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

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journal contribution
posted on 24.03.2004, 00:00 authored by 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
A new reverse turn, replacing one of the native type II‘ β-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.