TY - JOUR
T1 - Oligomers of glycamino acid
AU - Suhara, Yoshitomo
AU - Yamaguchi, Yoshiki
AU - Collins, Brian
AU - Schnaar, Ronald L.
AU - Yanagishita, Masaki
AU - Hildreth, James E.K.
AU - Shimada, Ichio
AU - Ichikawa, Yoshitaka
N1 - Funding Information:
We are grateful to Dr. K. Ikeda (University of Shizuoka, Japan) for performing the NMR experiments. Some of the NMR studies were performed in the Biochemistry NMR Facility at Johns Hopkins University, which was established by a grant from the National Institutes of Health (GM 27512) and a Biomedical Shared Instrumentation Grant (1S10-RR06262–0). A fellowship from Uehara Memorial Foundation (to Y.S.) is gratefully acknowledged. This research was partly supported by NIH grant GM52324 (to Y.I.).
PY - 2002
Y1 - 2002
N2 - 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.
AB - 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.
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U2 - 10.1016/S0968-0896(02)00020-2
DO - 10.1016/S0968-0896(02)00020-2
M3 - Article
C2 - 11937360
AN - SCOPUS:0036010349
SN - 0968-0896
VL - 10
SP - 1999
EP - 2013
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 6
ER -