An Unusual Reverse Turn Structure Adopted by a Furanoid Sugar Amino Acid Incorporated in Gramicidin S

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2004 Mar 18

PMID 15025470

Citations 6

Authors

Gijsbert M Grotenbreg

Mattie S M Timmer

Antonio L Llamas-Saiz

Martijn Verdoes

Gijsbert A van der Marel

Mark J van Raaij

Herman S Overkleeft

Mark Overhand

Affiliations

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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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