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

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The cyclopentene-based α,α-disubstituted α-amino acid Ac5c= and its homopeptides, up to nonapeptides, were synthesized. The side-chain cyclopentene was expected to become symmetric, the Cα-carbon to be puckered, and other Cβ, Cβ', Cγ, Cγ'-carbons to be coplanar. As expected, side-chain cyclopentene conformations became symmetric and Cα-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 α,α-disupstituted α-amino acid homopeptides.
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Keywords: CONFORMATION; CYCLOPENTENE; HELIX; PEPTIDE; α,α-DISUBSTITUTED α-AMINO ACID

Document Type: Research Article

Affiliations: 1: Graduate School of Biomedical Sciences Nagasaki University, 1-14 Bunkyo-machi Nagasaki 852-8521, Japan;, Email: [email protected] 2: School of Pharmaceutical Sciences Nagasaki University, 1-14 Bunkyo-machi Nagasaki 852-8521, Japan 3: Graduate School of Biomedical Sciences Nagasaki University, 1-14 Bunkyo-machi Nagasaki 852-8521, Japan 4: Osaka University of Pharmaceutical Sciences Osaka 569-1094, Japan

Publication date: 01 December 2018

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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