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Synthesis of chiral five‐membered carbocyclic ring amino acids with an acetal moiety and helical conformations of its homo‐chiral homopeptides
Author(s) -
Koba Yurie,
Hirata Yoko,
Ueda Atsushi,
Oba Makoto,
Doi Mitsunobu,
Demizu Yosuke,
Kurihara Masaaki,
Tanaka Masakazu
Publication year - 2016
Publication title -
peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.22769
Subject(s) - chemistry , moiety , acetal , ring (chemistry) , stereochemistry , chirality (physics) , organic chemistry , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark
Chiral five‐membered carbocyclic ring amino acids bearing various diol acetal moieties were synthesized starting from l ‐malic acid, and homo‐chiral homopeptides composed of cyclic amino acid (S)‐Ac 5 c 3EG bearing an ethylene glycol acetal, up to an octapeptide, were prepared. A conformational analysis revealed that (S)‐Ac 5 c 3EG homopeptides formed helical structures. (S)‐Ac 5 c 3EG homopeptides, up to hexapeptides, formed helical structures without controlling the helical screw direction, while (S)‐Ac 5 c 3EG hepta‐ and octapeptides formed helical structures with a preference for the left‐handed (M) helical‐screw direction. © 2015 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 106: 555–562, 2016.