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

Masakazu Tanaka | Zendy; Haruka Yakabi | Zendy; Haruki Nakatani | Zendy; Atsushi Ueda | Zendy; Mitsunobu Doi | Zendy; Makoto Oba | Zendy

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

Author(s) -

Masakazu Tanaka,

Haruka Yakabi,

Haruki Nakatani,

Atsushi Ueda,

Mitsunobu Doi,

Makoto Oba

Publication year - 2018

Publication title -

chimia international journal for chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.387

H-Index - 55

eISSN - 2673-2424

pISSN - 0009-4293

DOI - 10.2533/chimia.2018.848

Subject(s) - cyclopentene , cyclopentane , chemistry , side chain , crystallography , amino acid , stereochemistry , organic chemistry , polymer , biochemistry , catalysis

The cyclopentene-based ?,?-disubstituted ?-amino acid Ac5c= and its homopeptides, up to nonapeptides, were synthesized. The side-chain cyclopentene was expected to become symmetric, the C?-carbon to be puckered, and other C?, C?', C?, C?'-carbons to be coplanar. As expected, side-chain cyclopentene conformations became symmetric and C?-carbons were puckered. Conformational studies using FT-IR absorption, 1H NMR spectra, and X-ray crystallographic analyses revealed that Ac5c= homopeptides did not form a planar conformation, but assumed a 310-helical structure, similar to cyclopentane-based ?,?-disupstituted ?-amino acid homopeptides.

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