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Crystal structure of precorrin-8x methyl mutase.

Shipman LW, Li D, Roessner CA, Scott AI, Sacchettini JC
Structure 9 587-96 (2001)
Cited: 14 times
EuropePMC logo PMID: 11470433

Abstract

Background

The crystal structure of precorrin-8x methyl mutase (CobH), an enzyme of the aerobic pathway to vitamin B12, provides evidence that the mechanism for methyl migration can plausibly be regarded as an allowed [1,5]-sigmatropic shift of a methyl group from C-11 to C-12 at the C ring of precorrin-8x to afford hydrogenobyrinic acid.

Results

The dimeric structure of CobH creates a set of shared active sites that readily discriminate between different tautomers of precorrin-8x and select a discrete tautomer for sigmatropic rearrangement. The active site contains a strictly conserved histidine residue close to the site of methyl migration in ring C of the substrate.

Reviews - 1i1h mentioned but not cited (1)

  1. The requirement for cobalt in vitamin B12: A paradigm for protein metalation. Osman D, Cooke A, Young TR, Deery E, Robinson NJ, Warren MJ. Biochim Biophys Acta Mol Cell Res 1868 118896 (2021)

Articles - 1i1h mentioned but not cited (2)

  1. An enzyme-trap approach allows isolation of intermediates in cobalamin biosynthesis. Deery E, Schroeder S, Lawrence AD, Taylor SL, Seyedarabi A, Waterman J, Wilson KS, Brown D, Geeves MA, Howard MJ, Pickersgill RW, Warren MJ. Nat Chem Biol 8 933-940 (2012)
  2. Contribution to the prediction of the fold code: application to immunoglobulin and flavodoxin cases. Banach M, Prudhomme N, Carpentier M, Duprat E, Papandreou N, Kalinowska B, Chomilier J, Roterman I. PLoS One 10 e0125098 (2015)


Reviews citing this publication (3)

  1. Biosynthesis of the modified tetrapyrroles-the pigments of life. Bryant DA, Hunter CN, Warren MJ. J Biol Chem 295 6888-6925 (2020)
  2. Current developments and challenges in the search for a naturally selected Diels-Alderase. Kim HJ, Ruszczycky MW, Liu HW. Curr Opin Chem Biol 16 124-131 (2012)
  3. The expanding world of biosynthetic pericyclases: cooperation of experiment and theory for discovery. Jamieson CS, Ohashi M, Liu F, Tang Y, Houk KN. Nat Prod Rep 36 698-713 (2019)

Articles citing this publication (8)

  1. Asymmetric Enzymatic Synthesis of Allylic Amines: A Sigmatropic Rearrangement Strategy. Prier CK, Hyster TK, Farwell CC, Huang A, Arnold FH. Angew Chem Int Ed Engl 55 4711-4715 (2016)
  2. The crystal structure of MT0146/CbiT suggests that the putative precorrin-8w decarboxylase is a methyltransferase. Keller JP, Smith PM, Benach J, Christendat D, deTitta GT, Hunt JF. Structure 10 1475-1487 (2002)
  3. Structural basis for stereoselective dehydration and hydrogen-bonding catalysis by the SAM-dependent pericyclase LepI. Cai Y, Hai Y, Ohashi M, Jamieson CS, Garcia-Borras M, Houk KN, Zhou J, Tang Y. Nat Chem 11 812-820 (2019)
  4. Construction of Fluorescent Analogs to Follow the Uptake and Distribution of Cobalamin (Vitamin B12) in Bacteria, Worms, and Plants. Lawrence AD, Nemoto-Smith E, Deery E, Baker JA, Schroeder S, Brown DG, Tullet JMA, Howard MJ, Brown IR, Smith AG, Boshoff HI, Barry CE, Warren MJ. Cell Chem Biol 25 941-951.e6 (2018)
  5. Co(ll)-detection does not follow Kco(ll) gradient: channelling in Co(ll)-sensing. Patterson CJ, Pernil R, Dainty SJ, Chakrabarti B, Henry CE, Money VA, Foster AW, Robinson NJ. Metallomics 5 352-362 (2013)
  6. X-Ray snapshots of a pyridoxal enzyme: a catalytic mechanism involving concerted [1,5]-hydrogen sigmatropy in methionine γ-lyase. Sato D, Shiba T, Karaki T, Yamagata W, Nozaki T, Nakazawa T, Harada S. Sci Rep 7 4874 (2017)
  7. Crystal structure of a predicted precorrin-8x methylmutase from Thermoplasma acidophilum. Cuff ME, Miller DJ, Korolev S, Xu X, Anderson WF, Edwards A, Joachimiak A, Savchenko A. Proteins 58 751-754 (2005)
  8. The crystal structure of putative precorrin isomerase CbiC in cobalamin biosynthesis. Xue Y, Wei Z, Li X, Gong W. J Struct Biol 153 307-311 (2006)


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