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Conformational Studies on Peptides of α‐Aminoxy Acids with Functionalized Side‐Chains
Author(s) -
Yang Dan,
Liu GuoJun,
Hao Yu,
Li Wei,
Dong ZeMin,
Zhang DanWei,
Zhu NianYong
Publication year - 2010
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200900636
Subject(s) - side chain , chemistry , intramolecular force , hydrogen bond , methanol , peptide , cyclic peptide , stereochemistry , combinatorial chemistry , polymer chemistry , organic chemistry , molecule , polymer , biochemistry
Peptides of homochiral α‐aminoxy acids of nonpolar side chains can form a 1.8 8 ‐helix. In this paper, we report the conformational studies of α‐aminoxy peptides 1 , 2 , 3 , which have functionalized side chains, in both nonpolar and polar solvents. 1 H NMR, XRD, and FTIR absorption studies confirm the presence of the eight‐membered‐ring intramolecular hydrogen bonds (the N‐O turns) in nonpolar solvents as well as in methanol. CD studies of peptides 1 , 2 , 3 in different solvents indicate that a substantial degree of helical content is retained in methanol and acidic aqueous buffers. The introduction of functionalized side chains in α‐aminoxy peptides provides opportunities for designing biologically active peptides.