Helical Structures of Cyclopentene-based α,α-Disubstituted α-Amino Acid Homopeptides

被引：1

作者：

Tanaka, Masakazu ^{[1
]}

Yakabi, Haruka ^{[2
]}

Nakatani, Haruki ^{[2
]}

Ueda, Atsushi ^{[1
]}

Doi, Mitsunobu ^{[3
]}

Oba, Makoto ^{[1
]}

机构：

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

[2] Nagasaki Univ, Sch Pharmaceut Sci, 1-14 Bunkyo Machi, Nagasaki 8528521, Japan

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

来源：

CHIMIA | 2018年 / 72卷 / 12期

关键词：

Conformation; Cyclopentene; alpha; alpha-Disubstituted alpha-amino acid; Helix; Peptide; X-RAY-DIFFRACTION; STEREOSELECTIVE-SYNTHESIS; C-ALPHA; ALPHA-DIALKYLATED GLYCINES; DIALKYLATED GLYCINES; PEPTIDES; VERSATILITY; CONFORMATION; ABSORPTION; HANDEDNESS; H-1-NMR;

D O I：

10.2533/chimia.2018.848

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The cyclopentene-based alpha,alpha-disubstituted alpha-amino acid Ac(5)c(=) and its homopeptides, up to nona-peptides, were synthesized. The side-chain cyclopentene was expected to become symmetric, the C-alpha-carbon to be puckered, and other C-beta, C-beta', C-gamma'-carbons to be coplanar. As expected, side-chain cyclopentene conformations became symmetric and Cu-carbons were puckered. Conformational studies using FT-IR absorption, H-1 NMR spectra, and X-ray crystallographic analyses revealed that Ac(5)c(=) homopeptides did not form a planar conformation, but assumed a 3(10)-helical structure, similar to cyclopentane-based alpha,alpha-disubstituted a-amino acid homopeptides.

引用

页码：848 / 852

页数：5

共 31 条

[31] Design, development, and scale-up of a selective meso-epoxide desymmetrization process [J].

Varie, David L. ;

Beck, Christopher ;

Borders, Sandra K. ;

Brady, Molly D. ;

Cronin, Jason S. ;

Ditsworth, Tracy K. ;

Hay, David A. ;

Hoard, David W. ;

Hoying, Richard C. ;

Linder, Ryan J. ;

Miller, Richard D. ;

Moher, Eric D. ;

Remacle, Jacob R. ;

Rieck, John A., III .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (03) :546-559

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