TY - JOUR
T1 - Oligo(4-aminopiperidine-4-carboxylic acid)
T2 - An unusual basic oligopeptide with an acid-induced helical conformation
AU - Cho, Joon Il
AU - Tanaka, Masahiro
AU - Sato, Sota
AU - Kinbara, Kazushi
AU - Aida, Takuzo
PY - 2010/9/29
Y1 - 2010/9/29
N2 - In sharp contrast with helical polypeptides carrying basic side chains, Api8, a basic oligopeptide containing the non-natural achiral amino acid 4-aminopiperidine-4-carboxylic acid (Api), adopts a helical conformation only in acidic media. Alkaline titration of a protonated Api8 oligomer appended with a leucine derivative at its N-terminus showed that disruption of its helical conformation occurs in a pH range of 7-10. NMR studies indicated that the piperidine groups in Api8, when nonprotonated, possibly interact with the proximal amide protons in the peptide backbone and hamper the formation of the H-bonding network responsible for the helical conformation. The helical structure is induced not only by protonation but also by acylation of the piperidine groups.
AB - In sharp contrast with helical polypeptides carrying basic side chains, Api8, a basic oligopeptide containing the non-natural achiral amino acid 4-aminopiperidine-4-carboxylic acid (Api), adopts a helical conformation only in acidic media. Alkaline titration of a protonated Api8 oligomer appended with a leucine derivative at its N-terminus showed that disruption of its helical conformation occurs in a pH range of 7-10. NMR studies indicated that the piperidine groups in Api8, when nonprotonated, possibly interact with the proximal amide protons in the peptide backbone and hamper the formation of the H-bonding network responsible for the helical conformation. The helical structure is induced not only by protonation but also by acylation of the piperidine groups.
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U2 - 10.1021/ja106118w
DO - 10.1021/ja106118w
M3 - Article
C2 - 20812686
AN - SCOPUS:77957167819
VL - 132
SP - 13176
EP - 13178
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 38
ER -