Peptide foldamers composed of six-membered ring α,α-disubstituted α-amino acids with two changeable chiral acetal moieties

TETRAHEDRON

卷:71

Article

Tanda, Kazuhiro¹  Eto, Ryo²  Kato, Kazuya²  Oba, Makoto²  Ueda, Atsushi²  Suemune, Hiroshi¹  Doi, Mitsunobu³  Demizu, Yosuke⁴  Kurihara, Masaaki⁴  Tanaka, Masakazu² 

[1] Kyushu Univ, Grad Sch Pharmaceut Sci, Fukuoka 8128582, Japan

[2] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan

[3] Osaka Univ Pharmaceut Sci, Osaka 5691094, Japan

[4] Natl Inst Hlth Sci, Div Organ Chem, Tokyo 1588501, Japan

关键词: Conformation;    Peptides;    Helix;    alpha,alpha-disubstituted alpha-amino acid;    Foldamer;   

DOI  :  10.1016/j.tet.2015.04.031

来源: Elsevier

【 摘 要 】

Chiral cyclic alpha,alpha-disubstituted alpha-amino acids with four chiral centers at their acetal moieties were synthesized. An X-ray crystallographic analysis of homo-chiral tripeptide with (2R,3R)-butane-2,3-diol acetal moieties revealed that the tripeptide formed both (P) and (M) helical structures, and all peptide main-chain N(i)-H were intramolecularly hydrogen-bonded with the side-chain acetal -O- of the same amino acid residues (i). The effect of the four chiral centers in the amino acid residue on the peptide backbone helical-screw control was very weak. (C) 2015 Elsevier Ltd. All rights reserved.

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