Oligomers of glycamino acid

Yoshitomo Suhara, Yoshiki Yamaguchi, Brian Collins, Ronald L. Schnaar, Masaki Yanagishita, James E K Hildreth, Ichio Shimada, Yoshitaka Ichikawa

Research output: Contribution to journalArticle

55 Citations (Scopus)

Abstract

Glycamino acids, a family of sugar amino acids, are derivatives of C-glycosides that possesses a carboxyl group at the C-1 position and an amino group replacing one of the hydroxyl groups at either the C-2, 3, 4, or 6 position. We have prepared a series of glucose-type glycamino acids as monomeric building blocks: these are derivatives of 2-NH2-Glc-β-CO2H 1, 3-NH2-Glc-β-CO2H 2, 4-NH2-Glc-β-CO2H 3, and 6-NH2-Glc-β-CO2H 4 and constructed four types of homo-oligomers, β(1→2)-linked I, β(1→3)-linked II, β(1→4)-linked III, and β(1→6)-linked IV, employing the well-established N-Boc and BOP strategy. CD and NMR spectral studies of these oligomers suggested that only the β(1→2)-linked homo-oligomer possessed a helical structure that seems to be predetermined by the linkage position. Homo-oligomers with β(1→2)-linkages I and β(1→6)-linkages IV were also subjected to O-sulfation, and these O-sulfated oligomers were found to be able, in a linkage-specific manner, to effectively inhibit L-selectin-mediated cell adhesion, HIV infection, and heparanase activity without the anticoagulant activity associated with naturally occurring sulfated polysaccharides such as heparin.

Original languageEnglish
Pages (from-to)1999-2013
Number of pages15
JournalBioorganic and Medicinal Chemistry
Volume10
Issue number6
DOIs
Publication statusPublished - 2002
Externally publishedYes

Fingerprint

Oligomers
Acids
Derivatives
L-Selectin
Cell adhesion
Sugars
Hydroxyl Radical
Anticoagulants
Polysaccharides
Heparin
Nuclear magnetic resonance
Amino Acids
Glucose

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Suhara, Y., Yamaguchi, Y., Collins, B., Schnaar, R. L., Yanagishita, M., Hildreth, J. E. K., ... Ichikawa, Y. (2002). Oligomers of glycamino acid. Bioorganic and Medicinal Chemistry, 10(6), 1999-2013. https://doi.org/10.1016/S0968-0896(02)00020-2

Oligomers of glycamino acid. / Suhara, Yoshitomo; Yamaguchi, Yoshiki; Collins, Brian; Schnaar, Ronald L.; Yanagishita, Masaki; Hildreth, James E K; Shimada, Ichio; Ichikawa, Yoshitaka.

In: Bioorganic and Medicinal Chemistry, Vol. 10, No. 6, 2002, p. 1999-2013.

Research output: Contribution to journalArticle

Suhara, Y, Yamaguchi, Y, Collins, B, Schnaar, RL, Yanagishita, M, Hildreth, JEK, Shimada, I & Ichikawa, Y 2002, 'Oligomers of glycamino acid', Bioorganic and Medicinal Chemistry, vol. 10, no. 6, pp. 1999-2013. https://doi.org/10.1016/S0968-0896(02)00020-2
Suhara Y, Yamaguchi Y, Collins B, Schnaar RL, Yanagishita M, Hildreth JEK et al. Oligomers of glycamino acid. Bioorganic and Medicinal Chemistry. 2002;10(6):1999-2013. https://doi.org/10.1016/S0968-0896(02)00020-2
Suhara, Yoshitomo ; Yamaguchi, Yoshiki ; Collins, Brian ; Schnaar, Ronald L. ; Yanagishita, Masaki ; Hildreth, James E K ; Shimada, Ichio ; Ichikawa, Yoshitaka. / Oligomers of glycamino acid. In: Bioorganic and Medicinal Chemistry. 2002 ; Vol. 10, No. 6. pp. 1999-2013.
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