Literature DB >> 15025470

An unusual reverse turn structure adopted by a furanoid sugar amino acid incorporated in gramicidin S.

Gijsbert M Grotenbreg1, Mattie S M Timmer, Antonio L Llamas-Saiz, Martijn Verdoes, Gijsbert A van der Marel, Mark J van Raaij, Herman S Overkleeft, Mark Overhand.   

Abstract

A new reverse turn, replacing one of the native type II' beta-turns in the cyclic peptide antibiotic gramicidin S, induced by a furanoid sugar amino acid is revealed. The C3-hydroxyl function plays a pivotal role by acting as a H-bond acceptor, consequently flipping the amide bond between residues i and i + 1, as was established by NMR and X-ray crystallographic analysis.

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Year:  2004        PMID: 15025470     DOI: 10.1021/ja0397254

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  4 in total

1.  Damage of the bacterial cell envelope by antimicrobial peptides gramicidin S and PGLa as revealed by transmission and scanning electron microscopy.

Authors:  Mareike Hartmann; Marina Berditsch; Jacques Hawecker; Mohammad Fotouhi Ardakani; Dagmar Gerthsen; Anne S Ulrich
Journal:  Antimicrob Agents Chemother       Date:  2010-06-07       Impact factor: 5.191

Review 2.  Expanding the polypeptide backbone: hydrogen-bonded conformations in hybrid polypeptides containing the higher homologues of alpha-amino acids.

Authors:  Sunanda Chatterjee; Rituparna Sinha Roy; P Balaram
Journal:  J R Soc Interface       Date:  2007-08-22       Impact factor: 4.118

3.  Illuminating the dark conformational space of macrocycles using dominant rotors.

Authors:  Diego B Diaz; Solomon D Appavoo; Anastasia F Bogdanchikova; Yury Lebedev; Timothy J McTiernan; Gabriel Dos Passos Gomes; Andrei K Yudin
Journal:  Nat Chem       Date:  2021-02-15       Impact factor: 24.427

4.  Macrocycles: lessons from the distant past, recent developments, and future directions.

Authors:  Andrei K Yudin
Journal:  Chem Sci       Date:  2014-11-03       Impact factor: 9.825

  4 in total

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