An Unusual Reverse Turn Structure Adopted by a Furanoid Sugar Amino Acid Incorporated in Gramicidin S
Journal of the American Chemical Society2004Vol. 126(11), pp. 3444–3446
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Gijsbert M. Grotenbreg, Mattie S. M. Timmer, A.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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