title: An unusual reverse turn structure adopted by a furanoid sugar amino acid incorporated in gramicidin S.
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.
authors.affiliation: Leiden Institute of Chemistry, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
authors.forename: Gijsbert M
authors.initials: GM
authors.lastname: Grotenbreg
authors.forename: Mattie S M
authors.initials: MS
authors.lastname: Timmer
authors.forename: Antonio L
authors.initials: AL
authors.lastname: Llamas-Saiz
authors.forename: Martijn
authors.initials: M
authors.lastname: Verdoes
authors.forename: Gijsbert A
authors.initials: GA
authors.lastname: van der Marel
authors.forename: Mark J
authors.initials: MJ
authors.lastname: van Raaij
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
authors.forename: Mark
authors.initials: M
authors.lastname: Overhand
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D000606:Amino Sugars / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D006096:Gramicidin / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D011487:Protein Conformation
chemical_list: D000596:Amino Acids; D000606:Amino Sugars; D005663:Furans; D006096:Gramicidin