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Crystal structures of cephaibols.

Bunkóczi G, Schiell M, Vértesy L, Sheldrick GM
J Pept Sci 9 745-52
Related entries: 1ob4, 1ob6

Cited: 25 times
EuropePMC logo PMID: 14658793

Abstract

The crystal structures of the peptaibol antibiotics cephaibol A, cephaibol B and cephaibol C have been determined at ca. 0.9 A resolution. All three adopt a helical conformation with a sharp bend (of about 55 degrees) at the central hydroxyproline. All isovalines were found to possess the D configuration, superposition of all four models (there are two independent molecules in the cephaibol B structure) shows that the N-terminal helix is rigid and the C-terminus is flexible. There are differences in the hydrogen bonding patterns for the three structures that crystallize in different space groups despite relatively similar unit cell dimensions, but only in the case of cephaibol C does the packing emulate the formation of a membrane channel believed to be important for their biological function.

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Reviews citing this publication (1)

  1. Aib residues in peptaibiotics and synthetic sequences: analysis of nonhelical conformations. Aravinda S, Shamala N, Balaram P. Chem. Biodivers. 5 1238-1262 (2008)

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  10. The crystal structure of samarosporin I at atomic resolution. Gessmann R, Axford D, Evans G, Brückner H, Petratos K. J. Pept. Sci. 18 678-684 (2012)
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  12. The Emericellipsins A-E from an Alkalophilic Fungus Emericellopsis alkalina Show Potent Activity against Multidrug-Resistant Pathogenic Fungi. Kuvarina AE, Gavryushina IA, Kulko AB, Ivanov IA, Rogozhin EA, Georgieva ML, Sadykova VS. J Fungi (Basel) 7 153 (2021)
  13. Total synthesis of the peptaibols hypomurocin A3 and hypomurocin A5, and their conformation analysis. Pradeille N, Tzouros M, Möhle K, Linden A, Heimgartner H. Chem. Biodivers. 9 2528-2558 (2012)
  14. The achiral tetrapeptide Z-Aib-Aib-Aib-Gly-OtBu. Gessmann R, Brückner H, Petratos K. Acta Crystallogr C Struct Chem 70 1046-1049 (2014)
  15. A new density-modification procedure extending the application of the recent |ρ|-based phasing algorithm to larger crystal structures. Rius J, Torrelles X. Acta Crystallogr A Found Adv 77 339-347 (2021)
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  17. The crystal structure of the lipoaminopeptaibol helioferin, an antibiotic peptide from Mycogone rosea. Gessmann R, Brückner H, Berg A, Petratos K. Acta Crystallogr D Struct Biol 74 315-320 (2018)


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