Oligomers of glycamino acid

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

研究成果: Article

55 引用 (Scopus)

抄録

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.

元の言語English
ページ(範囲)1999-2013
ページ数15
ジャーナルBioorganic and Medicinal Chemistry
10
発行部数6
DOI
出版物ステータスPublished - 2002
外部発表Yes

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

これを引用

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.

:: Bioorganic and Medicinal Chemistry, 巻 10, 番号 6, 2002, p. 1999-2013.

研究成果: Article

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, 巻. 10, 番号 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 その他. 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. :: Bioorganic and Medicinal Chemistry. 2002 ; 巻 10, 番号 6. pp. 1999-2013.
@article{151f38c3f1df4dafa83e1045fe7917b5,
title = "Oligomers of glycamino acid",
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.",
author = "Yoshitomo Suhara and Yoshiki Yamaguchi and Brian Collins and Schnaar, {Ronald L.} and Masaki Yanagishita and Hildreth, {James E K} and Ichio Shimada and Yoshitaka Ichikawa",
year = "2002",
doi = "10.1016/S0968-0896(02)00020-2",
language = "English",
volume = "10",
pages = "1999--2013",
journal = "Bioorganic and Medicinal Chemistry",
issn = "0968-0896",
publisher = "Elsevier Limited",
number = "6",

}

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

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.

UR - http://www.scopus.com/inward/record.url?scp=0036010349&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0036010349&partnerID=8YFLogxK

U2 - 10.1016/S0968-0896(02)00020-2

DO - 10.1016/S0968-0896(02)00020-2

M3 - Article

C2 - 11937360

AN - SCOPUS:0036010349

VL - 10

SP - 1999

EP - 2013

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

SN - 0968-0896

IS - 6

ER -