1fp1 Citations

Structures of two natural product methyltransferases reveal the basis for substrate specificity in plant O-methyltransferases.

Nat Struct Biol 8 271-9 (2001)
Related entries: 1fp2, 1fpq, 6cig

Cited: 172 times
EuropePMC logo PMID: 11224575

Abstract

Chalcone O-methyltransferase (ChOMT) and isoflavone O-methyltransferase (IOMT) are S-adenosyl-l-methionine (SAM) dependent plant natural product methyltransferases involved in secondary metabolism in Medicago sativa (alfalfa). Here we report the crystal structure of ChOMT in complex with the product S-adenosyl-l-homocysteine and the substrate isoliquiritigenin (4,2',4'-trihydroxychalcone) refined to 1.8 A as well as the crystal structure of IOMT in complex with the products S-adenosyl-l-homocysteine and isoformononetin (4'-hydroxy-7-methoxyisoflavone) refined to 1.4 A. These two OMTs constitute the first plant methyltransferases to be structurally characterized and reveal a novel oligomerization domain and the molecular determinants for substrate selection. As such, this work provides a structural basis for understanding the substrate specificity of the diverse family of plant OMTs and facilitates the engineering of novel activities in this extensive class of natural product biosynthetic enzymes.

Reviews - 1fp1 mentioned but not cited (4)

  1. Many paths to methyltransfer: a chronicle of convergence. Schubert HL, Blumenthal RM, Cheng X. Trends Biochem Sci 28 329-335 (2003)
  2. Structure and function of enzymes involved in the biosynthesis of phenylpropanoids. Ferrer JL, Austin MB, Stewart C, Noel JP. Plant Physiol Biochem 46 356-370 (2008)
  3. AdoMet-dependent methylation, DNA methyltransferases and base flipping. Cheng X, Roberts RJ. Nucleic Acids Res 29 3784-3795 (2001)
  4. Molecular Origins of Functional Diversity in Benzylisoquinoline Alkaloid Methyltransferases. Morris JS, Facchini PJ. Front Plant Sci 10 1058 (2019)

Articles - 1fp1 mentioned but not cited (1)

  1. Structural and functional analysis of the pyocyanin biosynthetic protein PhzM from Pseudomonas aeruginosa. Parsons JF, Greenhagen BT, Shi K, Calabrese K, Robinson H, Ladner JE. Biochemistry 46 1821-1828 (2007)


Reviews citing this publication (26)

  1. Natural products and plant disease resistance. Dixon RA. Nature 411 843-847 (2001)
  2. The many faces of the helix-turn-helix domain: transcription regulation and beyond. Aravind L, Anantharaman V, Balaji S, Babu MM, Iyer LM. FEMS Microbiol Rev 29 231-262 (2005)
  3. Metabolic channeling in plants. Winkel BS. Annu Rev Plant Biol 55 85-107 (2004)
  4. Xanthohumol and related prenylflavonoids from hops and beer: to your good health! Stevens JF, Page JE. Phytochemistry 65 1317-1330 (2004)
  5. Rewriting the lignin roadmap. Humphreys JM, Chapple C. Curr Opin Plant Biol 5 224-229 (2002)
  6. Phytoestrogens. Dixon RA. Annu Rev Plant Biol 55 225-261 (2004)
  7. Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part I: Chemical diversity, impacts on plant biology and human health. Ververidis F, Trantas E, Douglas C, Vollmer G, Kretzschmar G, Panopoulos N. Biotechnol J 2 1214-1234 (2007)
  8. Melatonin biosynthesis in plants: multiple pathways catalyze tryptophan to melatonin in the cytoplasm or chloroplasts. Back K, Tan DX, Reiter RJ. J Pineal Res 61 426-437 (2016)
  9. Architectures, mechanisms and molecular evolution of natural product methyltransferases. Liscombe DK, Louie GV, Noel JP. Nat Prod Rep 29 1238-1250 (2012)
  10. Metabolome diversity: too few genes, too many metabolites? Schwab W. Phytochemistry 62 837-849 (2003)
  11. The evolutionary paths towards complexity: a metabolic perspective. Weng JK. New Phytol 201 1141-1149 (2014)
  12. Isoflavonoids of the leguminosae. Veitch NC. Nat Prod Rep 24 417-464 (2007)
  13. Floral benzenoid carboxyl methyltransferases: from in vitro to in planta function. Effmert U, Saschenbrecker S, Ross J, Negre F, Fraser CM, Noel JP, Dudareva N, Piechulla B. Phytochemistry 66 1211-1230 (2005)
  14. The enzymology of combinatorial biosynthesis. Reeves CD. Crit Rev Biotechnol 23 95-147 (2003)
  15. Evolution of morphine biosynthesis in opium poppy. Ziegler J, Facchini PJ, Geissler R, Schmidt J, Ammer C, Kramell R, Voigtländer S, Gesell A, Pienkny S, Brandt W. Phytochemistry 70 1696-1707 (2009)
  16. Enzyme mechanisms for sterol C-methylations. Nes WD. Phytochemistry 64 75-95 (2003)
  17. Putrescine N-methyltransferase--the start for alkaloids. Biastoff S, Brandt W, Dräger B. Phytochemistry 70 1708-1718 (2009)
  18. Structure, function, and engineering of enzymes in isoflavonoid biosynthesis. Wang X. Funct Integr Genomics 11 13-22 (2011)
  19. Enzymes in the biosynthesis of aromatic polyketide antibiotics. Schneider G. Curr Opin Struct Biol 15 629-636 (2005)
  20. Echinomycin biosynthesis. Sato M, Nakazawa T, Tsunematsu Y, Hotta K, Watanabe K. Curr Opin Chem Biol 17 537-545 (2013)
  21. Natural Products Impacting DNA Methyltransferases and Histone Deacetylases. Akone SH, Ntie-Kang F, Stuhldreier F, Ewonkem MB, Noah AM, Mouelle SEM, Müller R. Front Pharmacol 11 992 (2020)
  22. Recent Advances in Heterologous Synthesis Paving Way for Future Green-Modular Bioindustries: A Review With Special Reference to Isoflavonoids. Sajid M, Stone SR, Kaur P. Front Bioeng Biotechnol 9 673270 (2021)
  23. Genome-guided exploration of metabolic features of Streptomyces peucetius ATCC 27952: past, current, and prospect. Thuan NH, Dhakal D, Pokhrel AR, Chu LL, Van Pham TT, Shrestha A, Sohng JK. Appl Microbiol Biotechnol 102 4355-4370 (2018)
  24. Diversification of Chemical Structures of Methoxylated Flavonoids and Genes Encoding Flavonoid-O-Methyltransferases. Liu Y, Fernie AR, Tohge T. Plants (Basel) 11 564 (2022)
  25. Current perspectives on the beneficial effects of soybean isoflavones and their metabolites on plants. Kim IS. Food Sci Biotechnol 31 515-526 (2022)
  26. Functional Diversification and Structural Origins of Plant Natural Product Methyltransferases. Lashley A, Miller R, Provenzano S, Jarecki SA, Erba P, Salim V. Molecules 28 43 (2022)

Articles citing this publication (141)

  1. Functional analysis of genetic variation in catechol-O-methyltransferase (COMT): effects on mRNA, protein, and enzyme activity in postmortem human brain. Chen J, Lipska BK, Halim N, Ma QD, Matsumoto M, Melhem S, Kolachana BS, Hyde TM, Herman MM, Apud J, Egan MF, Kleinman JE, Weinberger DR. Am J Hum Genet 75 807-821 (2004)
  2. Structure and stability of cohesin's Smc1-kleisin interaction. Haering CH, Schoffnegger D, Nishino T, Helmhart W, Nasmyth K, Löwe J. Mol Cell 15 951-964 (2004)
  3. Natural history of S-adenosylmethionine-binding proteins. Kozbial PZ, Mushegian AR. BMC Struct Biol 5 19 (2005)
  4. Structural basis for substrate recognition in the salicylic acid carboxyl methyltransferase family. Zubieta C, Ross JR, Koscheski P, Yang Y, Pichersky E, Noel JP. Plant Cell 15 1704-1716 (2003)
  5. Structural basis for the modulation of lignin monomer methylation by caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase. Zubieta C, Kota P, Ferrer JL, Dixon RA, Noel JP. Plant Cell 14 1265-1277 (2002)
  6. Characterization of phenylpropene O-methyltransferases from sweet basil: facile change of substrate specificity and convergent evolution within a plant O-methyltransferase family. Gang DR, Lavid N, Zubieta C, Chen F, Beuerle T, Lewinsohn E, Noel JP, Pichersky E. Plant Cell 14 505-519 (2002)
  7. Structure, function, and evolution of plant O-methyltransferases. Lam KC, Ibrahim RK, Behdad B, Dayanandan S. Genome 50 1001-1013 (2007)
  8. Molecular cloning of a plant N-acetylserotonin methyltransferase and its expression characteristics in rice. Kang K, Kong K, Park S, Natsagdorj U, Kim YS, Back K. J Pineal Res 50 304-309 (2011)
  9. Water deficits affect caffeate O-methyltransferase, lignification, and related enzymes in maize leaves. A proteomic investigation. Vincent D, Lapierre C, Pollet B, Cornic G, Negroni L, Zivy M. Plant Physiol 137 949-960 (2005)
  10. EST analysis of hop glandular trichomes identifies an O-methyltransferase that catalyzes the biosynthesis of xanthohumol. Nagel J, Culley LK, Lu Y, Liu E, Matthews PD, Stevens JF, Page JE. Plant Cell 20 186-200 (2008)
  11. Crystal structures of alfalfa caffeoyl coenzyme A 3-O-methyltransferase. Ferrer JL, Zubieta C, Dixon RA, Noel JP. Plant Physiol 137 1009-1017 (2005)
  12. A novel Mg(2+)-dependent O-methyltransferase in the phenylpropanoid metabolism of Mesembryanthemum crystallinum. Ibdah M, Zhang XH, Schmidt J, Vogt T. J Biol Chem 278 43961-43972 (2003)
  13. Identification in methicillin-susceptible Staphylococcus hominis of an active primordial mobile genetic element for the staphylococcal cassette chromosome mec of methicillin-resistant Staphylococcus aureus. Katayama Y, Takeuchi F, Ito T, Ma XX, Ui-Mizutani Y, Kobayashi I, Hiramatsu K. J Bacteriol 185 2711-2722 (2003)
  14. Mechanism of histone lysine methyl transfer revealed by the structure of SET7/9-AdoMet. Kwon T, Chang JH, Kwak E, Lee CW, Joachimiak A, Kim YC, Lee J, Cho Y. EMBO J 22 292-303 (2003)
  15. Elucidation of the final reactions of DIMBOA-glucoside biosynthesis in maize: characterization of Bx6 and Bx7. Jonczyk R, Schmidt H, Osterrieder A, Fiesselmann A, Schullehner K, Haslbeck M, Sicker D, Hofmann D, Yalpani N, Simmons C, Frey M, Gierl A. Plant Physiol 146 1053-1063 (2008)
  16. The structure of the RlmB 23S rRNA methyltransferase reveals a new methyltransferase fold with a unique knot. Michel G, Sauvé V, Larocque R, Li Y, Matte A, Cygler M. Structure 10 1303-1315 (2002)
  17. Local differentiation of sugar donor specificity of flavonoid glycosyltransferase in Lamiales. Noguchi A, Horikawa M, Fukui Y, Fukuchi-Mizutani M, Iuchi-Okada A, Ishiguro M, Kiso Y, Nakayama T, Ono E. Plant Cell 21 1556-1572 (2009)
  18. Flavonoid 3'-O-methyltransferase from rice: cDNA cloning, characterization and functional expression. Kim BG, Lee Y, Hur HG, Lim Y, Ahn JH. Phytochemistry 67 387-394 (2006)
  19. Elicitor-induced association of isoflavone O-methyltransferase with endomembranes prevents the formation and 7-O-methylation of daidzein during isoflavonoid phytoalexin biosynthesis. Liu CJ, Dixon RA. Plant Cell 13 2643-2658 (2001)
  20. Application of carborundum abrasion for investigating the leaf epidermis: molecular cloning of Catharanthus roseus 16-hydroxytabersonine-16-O-methyltransferase. Levac D, Murata J, Kim WS, De Luca V. Plant J 53 225-236 (2008)
  21. Structural basis for dual functionality of isoflavonoid O-methyltransferases in the evolution of plant defense responses. Liu CJ, Deavours BE, Richard SB, Ferrer JL, Blount JW, Huhman D, Dixon RA, Noel JP. Plant Cell 18 3656-3669 (2006)
  22. Structure-function analyses of a caffeic acid O-methyltransferase from perennial ryegrass reveal the molecular basis for substrate preference. Louie GV, Bowman ME, Tu Y, Mouradov A, Spangenberg G, Noel JP. Plant Cell 22 4114-4127 (2010)
  23. Characterization of three O-methyltransferases involved in noscapine biosynthesis in opium poppy. Dang TT, Facchini PJ. Plant Physiol 159 618-631 (2012)
  24. Structural, biochemical, and phylogenetic analyses suggest that indole-3-acetic acid methyltransferase is an evolutionarily ancient member of the SABATH family. Zhao N, Ferrer JL, Ross J, Guan J, Yang Y, Pichersky E, Noel JP, Chen F. Plant Physiol 146 455-467 (2008)
  25. Biosynthesis of 8-O-Methylated Benzoxazinoid Defense Compounds in Maize. Handrick V, Robert CA, Ahern KR, Zhou S, Machado RA, Maag D, Glauser G, Fernandez-Penny FE, Chandran JN, Rodgers-Melnik E, Schneider B, Buckler ES, Boland W, Gershenzon J, Jander G, Erb M, Köllner TG. Plant Cell 28 1682-1700 (2016)
  26. Molecular cloning of melatonin 2-hydroxylase responsible for 2-hydroxymelatonin production in rice (Oryza sativa). Byeon Y, Back K. J Pineal Res 58 343-351 (2015)
  27. Molecular cloning of columbamine O-methyltransferase from cultured Coptis japonica cells. Morishige T, Dubouzet E, Choi KB, Yazaki K, Sato F. Eur J Biochem 269 5659-5667 (2002)
  28. In silico analysis highlights the frequency and diversity of type 1 lantibiotic gene clusters in genome sequenced bacteria. Marsh AJ, O'Sullivan O, Ross RP, Cotter PD, Hill C. BMC Genomics 11 679 (2010)
  29. The actinomycin biosynthetic gene cluster of Streptomyces chrysomallus: a genetic hall of mirrors for synthesis of a molecule with mirror symmetry. Keller U, Lang M, Crnovcic I, Pfennig F, Schauwecker F. J Bacteriol 192 2583-2595 (2010)
  30. Biosynthesis of the major scent components 3,5-dimethoxytoluene and 1,3,5-trimethoxybenzene by novel rose O-methyltransferases. Scalliet G, Journot N, Jullien F, Baudino S, Magnard JL, Channelière S, Vergne P, Dumas C, Bendahmane M, Cock JM, Hugueney P. FEBS Lett 523 113-118 (2002)
  31. Biochemical and structural analysis of substrate promiscuity in plant Mg2+-dependent O-methyltransferases. Kopycki JG, Rauh D, Chumanevich AA, Neumann P, Vogt T, Stubbs MT. J Mol Biol 378 154-164 (2008)
  32. Flavivirus RNA cap methyltransferase: structure, function, and inhibition. Liu L, Dong H, Chen H, Zhang J, Ling H, Li Z, Shi PY, Li H. Front Biol (Beijing) 5 286-303 (2010)
  33. Scent evolution in Chinese roses. Scalliet G, Piola F, Douady CJ, Réty S, Raymond O, Baudino S, Bordji K, Bendahmane M, Dumas C, Cock JM, Hugueney P. Proc Natl Acad Sci U S A 105 5927-5932 (2008)
  34. cDNA cloning and biochemical characterization of S-adenosyl-L-methionine: 2,7,4'-trihydroxyisoflavanone 4'-O-methyltransferase, a critical enzyme of the legume isoflavonoid phytoalexin pathway. Akashi T, Sawada Y, Shimada N, Sakurai N, Aoki T, Ayabe S. Plant Cell Physiol 44 103-112 (2003)
  35. Functional characterization of a novel benzylisoquinoline O-methyltransferase suggests its involvement in papaverine biosynthesis in opium poppy (Papaver somniferum L). Pienkny S, Brandt W, Schmidt J, Kramell R, Ziegler J. Plant J 60 56-67 (2009)
  36. Genetic analysis of the biosynthesis of 2-methoxy-3-isobutylpyrazine, a major grape-derived aroma compound impacting wine quality. Guillaumie S, Ilg A, Réty S, Brette M, Trossat-Magnin C, Decroocq S, Léon C, Keime C, Ye T, Baltenweck-Guyot R, Claudel P, Bordenave L, Vanbrabant S, Duchêne E, Delrot S, Darriet P, Hugueney P, Gomès E. Plant Physiol 162 604-615 (2013)
  37. Independent recruitment of an O-methyltransferase for syringyl lignin biosynthesis in Selaginella moellendorffii. Weng JK, Akiyama T, Ralph J, Chapple C. Plant Cell 23 2708-2724 (2011)
  38. Temporal global expression data reveal known and novel salicylate-impacted processes and regulators mediating powdery mildew growth and reproduction on Arabidopsis. Chandran D, Tai YC, Hather G, Dewdney J, Denoux C, Burgess DG, Ausubel FM, Speed TP, Wildermuth MC. Plant Physiol 149 1435-1451 (2009)
  39. The subcellular organization of strictosidine biosynthesis in Catharanthus roseus epidermis highlights several trans-tonoplast translocations of intermediate metabolites. Guirimand G, Guihur A, Ginis O, Poutrain P, Héricourt F, Oudin A, Lanoue A, St-Pierre B, Burlat V, Courdavault V. FEBS J 278 749-763 (2011)
  40. Functional analysis of members of the isoflavone and isoflavanone O-methyltransferase enzyme families from the model legume Medicago truncatula. Deavours BE, Liu CJ, Naoumkina MA, Tang Y, Farag MA, Sumner LW, Noel JP, Dixon RA. Plant Mol Biol 62 715-733 (2006)
  41. Crystal structure and functional mapping of human ASMT, the last enzyme of the melatonin synthesis pathway. Botros HG, Legrand P, Pagan C, Bondet V, Weber P, Ben-Abdallah M, Lemière N, Huguet G, Bellalou J, Maronde E, Beguin P, Haouz A, Shepard W, Bourgeron T. J Pineal Res 54 46-57 (2013)
  42. Two O-methyltransferases involved in the biosynthesis of methoxypyrazines: grape-derived aroma compounds important to wine flavour. Dunlevy JD, Soole KL, Perkins MV, Dennis EG, Keyzers RA, Kalua CM, Boss PK. Plant Mol Biol 74 77-89 (2010)
  43. Predicting the substrates of cloned plant O-methyltransferases. Schröder G, Wehinger E, Schröder J. Phytochemistry 59 1-8 (2002)
  44. The key role of phloroglucinol O-methyltransferase in the biosynthesis of Rosa chinensis volatile 1,3,5-trimethoxybenzene. Wu S, Watanabe N, Mita S, Dohra H, Ueda Y, Shibuya M, Ebizuka Y. Plant Physiol 135 95-102 (2004)
  45. Role of COMT in ADHD: a systematic meta-analysis. Sun H, Yuan F, Shen X, Xiong G, Wu J. Mol Neurobiol 49 251-261 (2014)
  46. Elucidation of the biosynthetic pathway of the allelochemical sorgoleone using retrobiosynthetic NMR analysis. Dayan FE, Kagan IA, Rimando AM. J Biol Chem 278 28607-28611 (2003)
  47. Furanocoumarin biosynthesis in Ammi majus L. Cloning of bergaptol O-methyltransferase. Hehmann M, Lukacin R, Ekiert H, Matern U. Eur J Biochem 271 932-940 (2004)
  48. A methyltransferase essential for the methoxypyrazine-derived flavour of wine. Dunlevy JD, Dennis EG, Soole KL, Perkins MV, Davies C, Boss PK. Plant J 75 606-617 (2013)
  49. A set of regioselective O-methyltransferases gives rise to the complex pattern of methoxylated flavones in sweet basil. Berim A, Hyatt DC, Gang DR. Plant Physiol 160 1052-1069 (2012)
  50. Crystal structure of norcoclaurine-6-O-methyltransferase, a key rate-limiting step in the synthesis of benzylisoquinoline alkaloids. Robin AY, Giustini C, Graindorge M, Matringe M, Dumas R. Plant J 87 641-653 (2016)
  51. Putrescine N-methyltransferases--a structure-function analysis. Teuber M, Azemi ME, Namjoyan F, Meier AC, Wodak A, Brandt W, Dräger B. Plant Mol Biol 63 787-801 (2007)
  52. Two O-methyltransferases isolated from flower petals of Rosa chinensis var. spontanea involved in scent biosynthesis. Wu S, Watanabe N, Mita S, Ueda Y, Shibuya M, Ebizuka Y. J Biosci Bioeng 96 119-128 (2003)
  53. Genetic Control and Evolution of Anthocyanin Methylation. Provenzano S, Spelt C, Hosokawa S, Nakamura N, Brugliera F, Demelis L, Geerke DP, Schubert A, Tanaka Y, Quattrocchio F, Koes R. Plant Physiol 165 962-977 (2014)
  54. The crystal structure of the novobiocin biosynthetic enzyme NovP: the first representative structure for the TylF O-methyltransferase superfamily. Gómez García I, Stevenson CE, Usón I, Freel Meyers CL, Walsh CT, Lawson DM. J Mol Biol 395 390-407 (2010)
  55. Crystal structure of aclacinomycin-10-hydroxylase, a S-adenosyl-L-methionine-dependent methyltransferase homolog involved in anthracycline biosynthesis in Streptomyces purpurascens. Jansson A, Niemi J, Lindqvist Y, Mäntsälä P, Schneider G. J Mol Biol 334 269-280 (2003)
  56. In planta production of the highly potent resveratrol analogue pterostilbene via stilbene synthase and O-methyltransferase co-expression. Rimando AM, Pan Z, Polashock JJ, Dayan FE, Mizuno CS, Snook ME, Liu CJ, Baerson SR. Plant Biotechnol J 10 269-283 (2012)
  57. Bisubstrate inhibitors for the enzyme catechol-O-methyltransferase (COMT): influence of inhibitor preorganisation and linker length between the two substrate moieties on binding affinity. Lerner C, Masjost B, Ruf A, Gramlich V, Jakob-Roetne R, Zürcher G, Borroni E, Diederich F. Org Biomol Chem 1 42-49 (2003)
  58. Systematic analysis of O-methyltransferase gene family and identification of potential members involved in the formation of O-methylated flavonoids in Citrus. Liu X, Luo Y, Wu H, Xi W, Yu J, Zhang Q, Zhou Z. Gene 575 458-472 (2016)
  59. The O-methyltransferase gene MdoOMT1 is required for biosynthesis of methylated phenylpropenes in ripe apple fruit. Yauk YK, Chagné D, Tomes S, Matich AJ, Wang MY, Chen X, Maddumage R, Hunt MB, Rowan DD, Atkinson RG. Plant J 82 937-950 (2015)
  60. Molecular cloning and characterization of a flavonoid-O-methyltransferase with broad substrate specificity and regioselectivity from Citrus depressa. Itoh N, Iwata C, Toda H. BMC Plant Biol 16 180 (2016)
  61. beta-alanine N-methyltransferase of Limonium latifolium. cDNA cloning and functional expression of a novel N-methyltransferase implicated in the synthesis of the osmoprotectant beta-alanine betaine. Raman SB, Rathinasabapathi B. Plant Physiol 132 1642-1651 (2003)
  62. Crystal structure of dissimilatory sulfite reductase D (DsrD) protein--possible interaction with B- and Z-DNA by its winged-helix motif. Mizuno N, Voordouw G, Miki K, Sarai A, Higuchi Y. Structure 11 1133-1140 (2003)
  63. Crystal structures of BchU, a methyltransferase involved in bacteriochlorophyll c biosynthesis, and its complex with S-adenosylhomocysteine: implications for reaction mechanism. Wada K, Yamaguchi H, Harada J, Niimi K, Osumi S, Saga Y, Oh-Oka H, Tamiaki H, Fukuyama K. J Mol Biol 360 839-849 (2006)
  64. Investigation of the molecular origins of protein-arginine methyltransferase I (PRMT1) product specificity reveals a role for two conserved methionine residues. Gui S, Wooderchak WL, Daly MP, Porter PJ, Johnson SJ, Hevel JM. J Biol Chem 286 29118-29126 (2011)
  65. Tertiary structure of thiopurine methyltransferase from Pseudomonas syringae, a bacterial orthologue of a polymorphic, drug-metabolizing enzyme. Scheuermann TH, Lolis E, Hodsdon ME. J Mol Biol 333 573-585 (2003)
  66. Crystal structure of SAM-dependent O-methyltransferase from pathogenic bacterium Leptospira interrogans. Hou X, Wang Y, Zhou Z, Bao S, Lin Y, Gong W. J Struct Biol 159 523-528 (2007)
  67. Functional analysis of MycE and MycF, two O-methyltransferases involved in the biosynthesis of mycinamicin macrolide antibiotics. Li S, Anzai Y, Kinoshita K, Kato F, Sherman DH. Chembiochem 10 1297-1301 (2009)
  68. Methylation of sulfhydryl groups: a new function for a family of small molecule plant O-methyltransferases. Coiner H, Schröder G, Wehinger E, Liu CJ, Noel JP, Schwab W, Schröder J. Plant J 46 193-205 (2006)
  69. Probing the mysteries of lignin biosynthesis: the crystal structure of caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase provides new insights. Eckardt NA. Plant Cell 14 1185-1189 (2002)
  70. Crystal structure of guanidinoacetate methyltransferase from rat liver: a model structure of protein arginine methyltransferase. Komoto J, Huang Y, Takata Y, Yamada T, Konishi K, Ogawa H, Gomi T, Fujioka M, Takusagawa F. J Mol Biol 320 223-235 (2002)
  71. Molecular basis of substrate promiscuity for the SAM-dependent O-methyltransferase NcsB1, involved in the biosynthesis of the enediyne antitumor antibiotic neocarzinostatin. Cooke HA, Guenther EL, Luo Y, Shen B, Bruner SD. Biochemistry 48 9590-9598 (2009)
  72. O-Methylation of benzaldehyde derivatives by "lignin specific" caffeic acid 3-O-methyltransferase. Kota P, Guo D, Zubieta C, Noel J, Dixon RA. Phytochemistry 65 837-846 (2004)
  73. Unraveling Additional O-Methylation Steps in Benzylisoquinoline Alkaloid Biosynthesis in California Poppy (Eschscholzia californica). Purwanto R, Hori K, Yamada Y, Sato F. Plant Cell Physiol 58 1528-1540 (2017)
  74. Cloning and Phylogenetic Analysis of Brassica napus L. Caffeic Acid O-Methyltransferase 1 Gene Family and Its Expression Pattern under Drought Stress. Li W, Lu J, Lu K, Yuan J, Huang J, Du H, Li J. PLoS One 11 e0165975 (2016)
  75. Functional characterization of MpaG', the O-methyltransferase involved in the biosynthesis of mycophenolic acid. Zhang W, Cao S, Qiu L, Qi F, Li Z, Yang Y, Huang S, Bai F, Liu C, Wan X, Li S. Chembiochem 16 565-569 (2015)
  76. A Novel N-Methyltransferase in Arabidopsis Appears to Feed a Conserved Pathway for Nicotinate Detoxification among Land Plants and Is Associated with Lignin Biosynthesis. Li W, Zhang F, Wu R, Jia L, Li G, Guo Y, Liu C, Wang G. Plant Physiol 174 1492-1504 (2017)
  77. A radical S-adenosyl-L-methionine enzyme and a methyltransferase catalyze cyclopropane formation in natural product biosynthesis. Jin WB, Wu S, Jian XH, Yuan H, Tang GL. Nat Commun 9 2771 (2018)
  78. Statistical models for discerning protein structures containing the DNA-binding helix-turn-helix motif. McLaughlin WA, Berman HM. J Mol Biol 330 43-55 (2003)
  79. Structure-function relationships of wheat flavone O-methyltransferase: Homology modeling and site-directed mutagenesis. Zhou JM, Lee E, Kanapathy-Sinnaiaha F, Park Y, Kornblatt JA, Lim Y, Ibrahim RK. BMC Plant Biol 10 156 (2010)
  80. The three-dimensional structure of Arabidopsis thaliana O-methyltransferase predicted by homology-based modelling. Yang H, Ahn JH, Ibrahim RK, Lee S, Lim Y. J Mol Graph Model 23 77-87 (2004)
  81. Isolation and characterization of 27-O-demethylrifamycin SV methyltransferase provides new insights into the post-PKS modification steps during the biosynthesis of the antitubercular drug rifamycin B by Amycolatopsis mediterranei S699. Xu J, Mahmud T, Floss HG. Arch Biochem Biophys 411 277-288 (2003)
  82. Molecular Basis for Autocatalytic Backbone N-Methylation in RiPP Natural Product Biosynthesis. Ongpipattanakul C, Nair SK. ACS Chem Biol 13 2989-2999 (2018)
  83. Molecular Cloning and Functional Characterization of a Novel Isoflavone 3'-O-methyltransferase from Pueraria lobata. Li J, Li C, Gou J, Zhang Y. Front Plant Sci 7 793 (2016)
  84. S-adenosylmethionine-binding properties of a bacterial phospholipid N-methyltransferase. Aktas M, Gleichenhagen J, Stoll R, Narberhaus F. J Bacteriol 193 3473-3481 (2011)
  85. Structural and functional insights into O-methyltransferase from Bacillus cereus. Cho JH, Park Y, Ahn JH, Lim Y, Rhee S. J Mol Biol 382 987-997 (2008)
  86. A new structural form in the SAM/metal-dependent o‑methyltransferase family: MycE from the mycinamicin biosynthetic pathway. Akey DL, Li S, Konwerski JR, Confer LA, Bernard SM, Anzai Y, Kato F, Sherman DH, Smith JL. J Mol Biol 413 438-450 (2011)
  87. Characterization of an O-methyltransferase from soybean. Kim BG, Lee HJ, Park Y, Lim Y, Ahn JH. Plant Physiol Biochem 44 236-241 (2006)
  88. Cloning, Functional Characterization, and Catalytic Mechanism of a Bergaptol O-Methyltransferase from Peucedanum praeruptorum Dunn. Zhao Y, Wang N, Zeng Z, Xu S, Huang C, Wang W, Liu T, Luo J, Kong L. Front Plant Sci 7 722 (2016)
  89. PP2A-B'γ modulates foliar trans-methylation capacity and the formation of 4-methoxy-indol-3-yl-methyl glucosinolate in Arabidopsis leaves. Rahikainen M, Trotta A, Alegre S, Pascual J, Vuorinen K, Overmyer K, Moffatt B, Ravanel S, Glawischnig E, Kangasjärvi S. Plant J 89 112-127 (2017)
  90. Rational Reprogramming of O-Methylation Regioselectivity for Combinatorial Biosynthetic Tailoring of Benzenediol Lactone Scaffolds. Wang X, Wang C, Duan L, Zhang L, Liu H, Xu YM, Liu Q, Mao T, Zhang W, Chen M, Lin M, Gunatilaka AAL, Xu Y, Molnár I. J Am Chem Soc 141 4355-4364 (2019)
  91. Evolution of the key alkaloid enzyme putrescine N-methyltransferase from spermidine synthase. Junker A, Fischer J, Sichhart Y, Brandt W, Dräger B. Front Plant Sci 4 260 (2013)
  92. Heterodimeric O-methyltransferases involved in the biosynthesis of noscapine in opium poppy. Park MR, Chen X, Lang DE, Ng KKS, Facchini PJ. Plant J 95 252-267 (2018)
  93. Two types of O-methyltransferase are involved in biosynthesis of anticancer methoxylated 4'-deoxyflavones in Scutellaria baicalensis Georgi. Cui MY, Lu AR, Li JX, Liu J, Fang YM, Pei TL, Zhong X, Wei YK, Kong Y, Qiu WQ, Hu YH, Yang J, Chen XY, Martin C, Zhao Q. Plant Biotechnol J 20 129-142 (2022)
  94. Identifying Genes Involved in alkaloid Biosynthesis in Vinca minor Through Transcriptomics and Gene Co-Expression Analysis. Stander EA, Sepúlveda LJ, Dugé de Bernonville T, Carqueijeiro I, Koudounas K, Lemos Cruz P, Besseau S, Lanoue A, Papon N, Giglioli-Guivarc'h N, Dirks R, O'Connor SE, Atehortùa L, Oudin A, Courdavault V. Biomolecules 10 E1595 (2020)
  95. Overexpression of CrCOMT from Carex rigescens increases salt stress and modulates melatonin synthesis in Arabidopsis thaliana. Zhang K, Cui H, Cao S, Yan L, Li M, Sun Y. Plant Cell Rep 38 1501-1514 (2019)
  96. Structure and Biophysical Characterization of the S-Adenosylmethionine-dependent O-Methyltransferase PaMTH1, a Putative Enzyme Accumulating during Senescence of Podospora anserina. Chatterjee D, Kudlinzki D, Linhard V, Saxena K, Schieborr U, Gande SL, Wurm JP, Wöhnert J, Abele R, Rogov VV, Dötsch V, Osiewacz HD, Sreeramulu S, Schwalbe H. J Biol Chem 290 16415-16430 (2015)
  97. Molecular characterization of O-methyltransferases involved in isoquinoline alkaloid biosynthesis in Coptis japonica. Morishige T, Tamakoshi M, Takemura T, Sato F. Proc Jpn Acad Ser B Phys Biol Sci 86 757-768 (2010)
  98. MtmMII-mediated C-methylation during biosynthesis of the antitumor drug mithramycin is essential for biological activity and DNA-drug interaction. Rodríguez D, Quirós LM, Salas JA. J Biol Chem 279 8149-8158 (2004)
  99. Biochemical Studies of Mycobacterial Fatty Acid Methyltransferase: A Catalyst for the Enzymatic Production of Biodiesel. Petronikolou N, Nair SK. Chem Biol 22 1480-1490 (2015)
  100. O-Methyltransferases involved in biphenyl and dibenzofuran biosynthesis. Khalil MN, Brandt W, Beuerle T, Reckwell D, Groeneveld J, Hänsch R, Gaid MM, Liu B, Beerhues L. Plant J 83 263-276 (2015)
  101. Structural basis for modification of flavonol and naphthol glucoconjugates by Nicotiana tabacum malonyltransferase (NtMaT1). Manjasetty BA, Yu XH, Panjikar S, Taguchi G, Chance MR, Liu CJ. Planta 236 781-793 (2012)
  102. Defects in the synthetic pathway prevent DIF-1 mediated stalk lineage specification cascade in the non-differentiating social amoeba, Acytostelium subglobosum. Mohri K, Hata T, Kikuchi H, Oshima Y, Urushihara H. Biol Open 3 553-560 (2014)
  103. Molecular cloning and characterization of O-methyltransferases from the flower buds of Iris hollandica. Yoshihara N, Fukuchi-Mizutani M, Okuhara H, Tanaka Y, Yabuya T. J Plant Physiol 165 415-422 (2008)
  104. O-Methylation of phenylphenalenone phytoalexins in Musaacuminata and Wachendorfia thyrsiflora. Otálvaro F, Jitsaeng K, Munde T, Echeverri F, Quiñones W, Schneider B. Phytochemistry 71 206-213 (2010)
  105. Rhamnetin production based on the rational design of the poplar O-methyltransferase enzyme and its biological activities. Lee S, Shin SY, Lee Y, Park Y, Kim BG, Ahn JH, Chong Y, Lee YH, Lim Y. Bioorg Med Chem Lett 21 3866-3870 (2011)
  106. The Functional Characterization of a Site-Specific Apigenin 4'-O-methyltransferase Synthesized by the Liverwort Species Plagiochasma appendiculatum. Liu H, Xu RX, Gao S, Cheng AX. Molecules 22 E759 (2017)
  107. Unusual pseudosubstrate specificity of a novel 3,5-dimethoxyphenol O-methyltransferase cloned from Ruta graveolens L. Burga L, Wellmann F, Lukacin R, Witte S, Schwab W, Schröder J, Matern U. Arch Biochem Biophys 440 54-64 (2005)
  108. Catalytic specificity of pea O-methyltransferases suggests gene duplication for (+)-pisatin biosynthesis. Akashi T, VanEtten HD, Sawada Y, Wasmann CC, Uchiyama H, Ayabe S. Phytochemistry 67 2525-2530 (2006)
  109. Characterization of an O-methyltransferase specific to guaiacol-type benzenoids from the flowers of loquat (Eriobotrya japonica). Koeduka T, Kajiyama M, Furuta T, Suzuki H, Tsuge T, Matsui K. J Biosci Bioeng 122 679-684 (2016)
  110. Genome-Wide Comprehensive Analysis the Molecular Phylogenetic Evaluation and Tissue-Specific Expression of SABATH Gene Family in Salvia miltiorrhiza. Wang B, Wang S, Wang Z. Genes (Basel) 8 E365 (2017)
  111. A Comparative Genomic and Transcriptomic Survey Provides Novel Insights into N-Acetylserotonin Methyltransferase (ASMT) in Fish. Zhang K, Ruan Z, Li J, Bian C, You X, Coon SL, Shi Q. Molecules 22 E1653 (2017)
  112. Biochemical Characterization of a Flavonoid O-methyltransferase from Perilla Leaves and Its Application in 7-Methoxyflavonoid Production. Park HL, Lee JC, Lee K, Lee JM, Nam HJ, Bhoo SH, Lee TH, Lee SW, Cho MH. Molecules 25 E4455 (2020)
  113. Crystal structure of LepI, a multifunctional SAM-dependent enzyme which catalyzes pericyclic reactions in leporin biosynthesis. Chang Z, Ansbacher T, Zhang L, Yang Y, Ko TP, Zhang G, Liu W, Huang JW, Dai L, Guo RT, Major DT, Chen CC. Org Biomol Chem 17 2070-2076 (2019)
  114. Expression and functional analysis of the nobiletin biosynthesis-related gene CitOMT in citrus fruit. Seoka M, Ma G, Zhang L, Yahata M, Yamawaki K, Kan T, Kato M. Sci Rep 10 15288 (2020)
  115. Targeted knockout of the gene OsHOL1 removes methyl iodide emissions from rice plants. Carlessi M, Mariotti L, Giaume F, Fornara F, Perata P, Gonzali S. Sci Rep 11 17010 (2021)
  116. The O-methyltransferase SrsB catalyzes the decarboxylative methylation of alkylresorcylic acid during phenolic lipid biosynthesis by Streptomyces griseus. Nakano C, Funa N, Ohnishi Y, Horinouchi S. J Bacteriol 194 1544-1551 (2012)
  117. Activity of chalcones derived from 2,4,5-trimethoxybenzaldehyde against Meloidogyne exigua and in silico interaction of one chalcone with a putative caffeic acid 3-O-methyltransferase from Meloidogyne incognita. Nunes AS, Campos VP, Mascarello A, Stumpf TR, Chiaradia-Delatorre LD, Machado AR, Santos Júnior HM, Yunes RA, Nunes RJ, Oliveira DF. Exp Parasitol 135 661-668 (2013)
  118. Identification and Characterization of Two New S-Adenosylmethionine-Dependent Methyltransferase Encoding Genes Suggested Their Involvement in Stipe Elongation of Flammulina velutipes. Huang Q, Mukhtar I, Zhang Y, Wei Z, Han X, Huang R, Yan J, Xie B. Mycobiology 47 441-448 (2019)
  119. Sequence analysis, in silico modeling and docking studies of caffeoyl CoA-O-methyltransferase of Populus trichopora. Phogat N, Vindal V, Kumar V, Inampudi KK, Prasad NK. J Mol Model 16 1461-1471 (2010)
  120. Structural and expressional divergence of genes encoding O-methyltransferase in wheat. Jung JH, Hong MJ, Kim DY, Kim JY, Heo HY, Kim TH, Jang CS, Seo YW. Genome 51 856-869 (2008)
  121. Two O-methyltransferases from Picea abies: characterization and molecular basis of different reactivity. Kim BG, Kim DH, Sung SH, Kim DE, Chong Y, Ahn JH. Planta 232 837-844 (2010)
  122. Altered regioselectivity of a poplar O-methyltransferase, POMT-7. Kim BG, Lee YJ, Lee S, Lim Y, Cheong Y, Ahn JH. J Biotechnol 138 107-111 (2008)
  123. Detection of an O-methyltransferase synthesising acetosyringone in methyl jasmonate-treated tobacco cell-suspensions cultures. Negrel J, Javelle F, Wipf D. Phytochemistry 99 52-60 (2014)
  124. Elucidation of the methyl transfer mechanism catalyzed by chalcone O-methyltransferase: a density functional study. Cui FC, Pan XL, Liu W, Liu JY. J Comput Chem 32 3068-3074 (2011)
  125. Rational Design of Resveratrol O-methyltransferase for the Production of Pinostilbene. Herrera DP, Chánique AM, Martínez-Márquez A, Bru-Martínez R, Kourist R, Parra LP, Schüller A. Int J Mol Sci 22 4345 (2021)
  126. Role of Serine 286 in cosubstrate binding and catalysis of a flavonol O-methyltransferase. Kornblatt J, Muzac I, Lim Y, Ahn JH, Ibrahim RK. Biochem Cell Biol 82 531-537 (2004)
  127. Structure and mechanism of an antibiotics-synthesizing 3-hydroxykynurenine C-methyltransferase. Chen SC, Huang CH, Lai SJ, Liu JS, Fu PK, Tseng ST, Yang CS, Lai MC, Ko TP, Chen Y. Sci Rep 5 10100 (2015)
  128. The purification, crystallization and preliminary structural characterization of PhzM, a phenazine-modifying methyltransferase from Pseudomonas aeruginosa. Gohain N, Thomashow LS, Mavrodi DV, Blankenfeldt W. Acta Crystallogr Sect F Struct Biol Cryst Commun 62 887-890 (2006)
  129. A high-throughput screen for directed evolution of the natural product sulfotransferase LipB. Koryakina I, Neville J, Nonaka K, Van Lanen SG, Williams GJ. J Biomol Screen 16 845-851 (2011)
  130. A thorough analysis and categorization of bacterial interrupted adenylation domains, including previously unidentified families. Lundy TA, Mori S, Garneau-Tsodikova S. RSC Chem Biol 1 233-250 (2020)
  131. COMT Val158 Met moderates the link between rank and aggression in a non-human primate. Gutleb DR, Roos C, Noll A, Ostner J, Schülke O. Genes Brain Behav 17 e12443 (2018)
  132. Molecular cloning of an O-methyltransferase from adventitious roots of Carapichea ipecacuanha. Cheong BE, Takemura T, Yoshimatsu K, Sato F. Biosci Biotechnol Biochem 75 107-113 (2011)
  133. Alkaloids from flowers of Erythrina corallodendron. Zhao HE, Wu J, Xu FQ, Bao MF, Jin CS, Cai XH. Nat Prod Res 33 1298-1303 (2019)
  134. Crystal structures of PigF, an O-methyltransferase involved in the prodigiosin synthetic pathway, reveal an induced-fit substrate-recognition mechanism. Qiu S, Xu D, Xu M, Zhou H, Sun N, Zhang L, Zhao M, He J, Ran T, Sun B, Wang W. IUCrJ 9 316-327 (2022)
  135. Methyl allyl ether formation in plants: novel S-adenosyl L-methionine:coniferyl alcohol 9-O-methyltransferase from suspension cultures of three Linum species. Berim A, Schneider B, Petersen M. Plant Mol Biol 64 279-291 (2007)
  136. Molecular Characterisation of Flavanone O-methylation in Eucalyptus. Somaletha Chandran K, Humphries J, Goodger JQD, Woodrow IE. Int J Mol Sci 23 3190 (2022)
  137. A Permissive Amide N-Methyltransferase for Dithiolopyrrolones. Chen X, Johnson RM, Li B. ACS Catal 13 1899-1905 (2023)
  138. Identification and characterization of two Isatis indigotica O-methyltransferases methylating C-glycosylflavonoids. Tan Y, Yang J, Jiang Y, Sun S, Wei X, Wang R, Bu J, Li D, Kang L, Chen T, Guo J, Cui G, Tang J, Huang L. Hortic Res 9 uhac140 (2022)
  139. Mycobacterial MMAR_2193 catalyzes O-methylation of diverse polyketide cores. Giri GR, Saxena P. PLoS One 17 e0262241 (2022)
  140. Regioselective stilbene O-methylations in Saccharinae grasses. Lui ACW, Pow KC, Lin N, Lam LPY, Liu G, Godwin ID, Fan Z, Khoo CJ, Tobimatsu Y, Wang L, Hao Q, Lo C. Nat Commun 14 3462 (2023)
  141. Structure of methyltransferase RedM that forms the dimethylpyrrolinium of the bisindole reductasporine. Daniel-Ivad P, Ryan KS. J Biol Chem 300 105520 (2023)