Helical structures of L-Leu-based peptides having chiral six-membered ring amino acids

被引：3

作者：

Umeno, Tomohiro ^{[1
]}

Ueda, Atsushi ^{[1
]}

Oba, Makoto ^{[1
]}

Doi, Mitsunobu ^{[2
]}

Hirata, Takayuki ^{[3
]}

Suemune, Hiroshi ^{[3
]}

Tanaka, Masakazu ^{[1
]}

机构：

[1] Nagasaki Univ, Grad Sch Biomed Sci, 1-14 Bunkyo Machi, Nagasaki 8528521, Japan

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

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

来源：

TETRAHEDRON | 2016年 / 72卷 / 22期

基金：

日本科学技术振兴机构;

关键词：

Helix; Conformation; Peptide; Cyclic amino acid; alpha; alpha-Disubstituted alpha-amino acid; X-RAY-DIFFRACTION; C-ALPHA; ALPHA-DIALKYLATED GLYCINES; LINEAR OLIGOPEPTIDES; CRYSTALLOGRAPHIC CHARACTERIZATION; CONFORMATIONAL CHARACTERIZATION; ENANTIOSELECTIVE EPOXIDATION; STEREOSELECTIVE-SYNTHESIS; INFRARED-ABSORPTION; SECONDARY STRUCTURE; CIRCULAR-DICHROISM;

D O I：

10.1016/j.tet.2016.04.040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

L-Leu-based peptides having chiral six-membered ring amino acids: Boc-{L-Leu-L-Leu-[(1R,3R)- or (1S,3R)-Ac(6)c(3M)}n-OMe [n=1 (2), 2 (4), 3 (5)1, were synthesized. A conformational analysis using FTIR absorption and NOESY NMR spectra revealed that these hexa- and nonapeptides having (1R,3R)-Ac(6)c(3M) or (1S,3R)-Ac(6)c(3M) formed helical structures in CDCl3 solution, while that using CD spectra suggested that the nonapeptide 5b having (1S,3R)-Ac(6)c(3M) become more right-handed (P) alpha-helical than the nonapeptide 5a having (1R,3R)-Ac(6)c(3M) in TFE solution. An X-ray crystallographic analysis showed that the hexapeptide 4b having (1S,3R)-Ac(6)c(3M) formed a partially distorted right-handed (P) 3(10)-/alpha-helical structure in the crystal state, while the nonapeptides 5a and 5b having (1R,3R)-Ac(6)c(3M) or (1S,3R)-Ac(6)c(3M) formed similar right-handed (P) alpha-helical backbone structures. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：3124 / 3131

页数：8

共 28 条

[1] Helical L-Leu-Based Peptides Having Chiral Five-Membered Carbocyclic Ring Amino Acids with an Ethylene Acetal Moiety
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[3] Synthesis of Chiral α-Trifluoromethyl α,α-Disubstituted α-Amino Acids and Conformational Analysis of L-Leu-Based Peptides with (R)- or (S)-α-Trifluoromethylalanine
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