Chiral Centers in the side chains of α-amino acids control the helical screw sense of peptides

被引：65
|
作者：
Tanaka, M [1 ]
Demizu, Y
Doi, M
Kurihara, M
Suemune, H
机构：
[1] Kyushu Univ, Grad Sch Pharmaceut Sci, Fukuoka 8128582, Japan
[2] Osaka Univ Pharmaceut Sci, Takatsuki, Osaka 5691094, Japan
[3] Natl Inst Hlth Sci, Div Organ Chem, Tokyo 1588501, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 40期
关键词：
amino acids; chirality; conformation analysis; helical structures; peptidomimetics;
D O I：
10.1002/anie.200460420
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Chirality on the side suffices: The screw sense of 310- and α-helices formed by the oligopeptides 1, which have no α-carbon chiral centers, is controlled by the chiral centers in their side chains. These results imply that just the side chain chiral centers of isoleucine and threonine would affect the secondary structure of their oligopeptides.
引用
收藏
页码：5360 / 5363
页数：4
相关论文
共 50 条
  • [1] Side-chain chiral centers of amino acids and helical-screw handedness of their peptides
    Tanaka, M.
    Nagano, M.
    Demizu, Y.
    Anan, K.
    Kurihara, M.
    Doi, M.
    Suemune, H.
    JOURNAL OF PEPTIDE SCIENCE, 2006, 12 : 204 - 204
  • [2] Helical Screw-Sense Preferences of Peptides Based on Chiral, Cα-Tetrasubstituted α-Amino Acids
    Crisma, Marco
    Toniolo, Claudio
    BIOPOLYMERS, 2015, 104 (01) : 46 - 64
  • [3] Side-chain chiral centers of amino acid and helical-screw handedness of its peptides
    1600, American Chemical Society, Columbus, United States (127):
  • [4] Side-chain chiral centers of amino acid and helical-screw handedness of its peptides
    Tanaka, M
    Anan, K
    Demizu, Y
    Kurihara, M
    Doi, M
    Suemune, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) : 11570 - 11571
  • [5] Origin of Helical Screw Sense Selectivity Induced by Chiral Constrained Cα-Tetrasubstituted α-Amino Acids in Aib-based Peptides
    Maffucci, Irene
    Clayden, Jonathan
    Contini, Alessandro
    JOURNAL OF PHYSICAL CHEMISTRY B, 2015, 119 (44): : 14003 - 14013
  • [6] Terminal effect of chiral residue on helical screw sense in achiral peptides
    Inai, Y
    Kurokawa, Y
    Hirabayashi, T
    BIOPOLYMERS, 1999, 49 (07) : 551 - 564
  • [7] First optically active diarylpolysilanes:: Facile helical screw sense control with only (S)-enantiopure side chains
    Koe, JR
    Fujiki, M
    Nakashima, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) : 9734 - 9735
  • [8] Synthesis and Helical Structures of Poly(ω-alkynamide)s Having Chiral Side Chains: Effect of Solvent on Their Screw-Sense Inversion
    Suzuki, Yuji
    Miyagi, Yu
    Shiotsuki, Masashi
    Inai, Yoshihito
    Masuda, Toshio
    Sanda, Fumio
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (46) : 15131 - 15143
  • [9] Controlling the helical screw sense of oligopeptide by α-amino acid side-chain chirality
    Tanaka, Masakazu
    Demizu, Yosuke
    Doi, Mitsunobu
    Kurihara, Masaaki
    Suemune, Hiroshi
    Peptides 2004, Proceedings: BRIDGES BETWEEN DISCIPLINES, 2005, : 277 - 278
  • [10] Helical-screw handedness of peptides composed of diastereoisomeric cyclic amino acids
    Nagano, Masanobu
    Tanaka, Masakazu
    Doi, Mitsunobu
    Kurihara, Masaaki
    Suemune, Hiroshi
    JOURNAL OF PEPTIDE SCIENCE, 2008, 14 (08) : 51 - 51
12345