Efficient synthesis of carbopeptoid oligomers: insight into mimicry of β-peptide

Yoshitomo Suhara, Masaaki Kurihara, Atsushi Kittaka, Yoshitaka Ichikawa

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The ready access to a new class of carbohydrate mimetics was demonstrated by the synthesis of tetrameric carbopeptoids, in which glycosidic bonds were replaced with amide linkages. We herein describe the detailed synthetis method of β(1→2)- and β(1→6)-linked carbopeptoids starting from each d-glucosamine and d-glucose derivative. The building blocks were polymerized using BOP reagent and DIEA to form a homooligomer. These produced carbopeptoids are resistant to glycosidases and have interesting biological activity. With conformational analysis by molecular modeling calculation, β(1→2)-linked decamer showed a typical 16-helix form as a mimic of β-peptide. Therefore, our polysaccharide analogues have potential as peptide foldamers.

Original languageEnglish
Pages (from-to)8207-8217
Number of pages11
JournalTetrahedron
Volume62
Issue number34
DOIs
Publication statusPublished - 2006 Aug 21
Externally publishedYes

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Oligomers
Peptides
Molecular modeling
Glycoside Hydrolases
Glucosamine
Bioactivity
Amides
Polysaccharides
Carbohydrates
Derivatives
Glucose
benzotriazol-1-yloxy-tris(dimethylamino)phosphonium
N,N-diisopropylethylamine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Efficient synthesis of carbopeptoid oligomers : insight into mimicry of β-peptide. / Suhara, Yoshitomo; Kurihara, Masaaki; Kittaka, Atsushi; Ichikawa, Yoshitaka.

In: Tetrahedron, Vol. 62, No. 34, 21.08.2006, p. 8207-8217.

Research output: Contribution to journalArticle

Suhara, Yoshitomo ; Kurihara, Masaaki ; Kittaka, Atsushi ; Ichikawa, Yoshitaka. / Efficient synthesis of carbopeptoid oligomers : insight into mimicry of β-peptide. In: Tetrahedron. 2006 ; Vol. 62, No. 34. pp. 8207-8217.
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