SYNTHESIS AND EVALUATION OF SYNTHETIC ANALOGS OF DOLICHYL-P-P-CHITOBIOSE AS OLIGOSACCHARYLTRANSFERASE SUBSTRATES

被引：25

作者：

FANG, XG

GIBBS, BS

COWARD, JK

机构：

[1] UNIV MICHIGAN,DEPT CHEM,INTERDEPT PROGRAM MED CHEM,ANN ARBOR,MI 48109

[2] UNIV MICHIGAN,COLL PHARM,ANN ARBOR,MI 48109

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1995年 / 5卷 / 22期

关键词：

D O I：

10.1016/0960-894X(95)00460-B

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Five analogues of dolichylpyrophosphorylchitobiose containing shea, well defined lipid components were synthesized and evaluated as substrates for yeast oligosaccharyltransferase. All of the modified lipids led to a large decrease in enzyme-catalyzed glycosylation of the peptide substrate, BzAsnLeuThrNH(2), thus indicating a critical role for the polyisoprene, dolichol, in anchoring the oligosaccharide donor during catalysis.

引用

页码：2701 / 2706

页数：6

共 20 条

[1]

Lee, Coward, J. Org. Chem., 57, (1992)

[2]

Lee, Coward, Biochemistry, 32, (1993)

[3]

Imperiali, Zimmerman, Tetrahedron Lett., 29, (1988)

[4]

Kennedy, Carbohydrate Chemistry, (1988)

[5]

Robbins, Hubbard, Turco, Wirth, Cell, 12, (1977)

[6]

Flitsch, Pinches, Taylor, Turner, Chemo-enzymatic synthesis of a lipid-linked core trisaccharide of N-linked glycoproteins, Journal of the Chemical Society, Perkin Transactions 1, (1992)

[7]

Revers, Wilson, Webberly, Flitsch, Biochem. J., 299, (1994)

[8]

Rush, Shelling, Zingg, Ray, Waechter, J. Biol. Chem., 268, (1993)

[9]

Danilov, Chojnacki, FEBS Lett., 131, (1981)

[10]

Perich, Johns, Di-tert-butylN,N-Diethylphosphoramidite. A New Phosphitylating Agent for the Efficient Phosphorylation of Alcohols, Synthesis, (1988)

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