Synthesis of Galβ1→3 (Fucα1→4) GlcNAcβ-OR as potential acceptors for a new member of the α-1,2-L-fucosyltransferase family

Rakesh K. Jain; Sushama M. Pawar; E. V. Chandrasekaran; Conrad F. Piskorz; Khushi L. Matta

doi:10.1016/S0960-894X(00)80342-X

Synthesis of Galβ1→3 (Fucα1→4) GlcNAcβ-OR as potential acceptors for a new member of the α-1,2-L-fucosyltransferase family

Rakesh K. Jain
, Sushama M. Pawar
, E. V. Chandrasekaran
, Conrad F. Piskorz
, Khushi L. Matta

Department of Chemical and Biological Engineering

Roswell Park Cancer Institute

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

A stereoselective synthesis of Galβ1→3 (Fucα1→4) GlcNAcβ-Or (Lewis a) structures containing an anomeric p-nitrophenyl or benzyl group was accomplished through the use of methyl 3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranosid e. The compounds were used as acceptors to show in human ovarian tumors and a colon carcinoma cell line (Colo 205), the presence of a new type of α1,2-L-fucosyltransferase which converts the blood group determinant Lewis^a to Lewis^b.

Original language	English
Pages (from-to)	1333-1338
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	3
Issue number	6
DOIs	https://doi.org/10.1016/S0960-894X(00)80342-X
State	Published - Jun 1993

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title = "Synthesis of Galβ1→3 (Fucα1→4) GlcNAcβ-OR as potential acceptors for a new member of the α-1,2-L-fucosyltransferase family",

abstract = "A stereoselective synthesis of Galβ1→3 (Fucα1→4) GlcNAcβ-Or (Lewis a) structures containing an anomeric p-nitrophenyl or benzyl group was accomplished through the use of methyl 3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranosid e. The compounds were used as acceptors to show in human ovarian tumors and a colon carcinoma cell line (Colo 205), the presence of a new type of α1,2-L-fucosyltransferase which converts the blood group determinant Lewisa to Lewisb.",

author = "Jain, \{Rakesh K.\} and Pawar, \{Sushama M.\} and Chandrasekaran, \{E. V.\} and Piskorz, \{Conrad F.\} and Matta, \{Khushi L.\}",

year = "1993",

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doi = "10.1016/S0960-894X(00)80342-X",

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T1 - Synthesis of Galβ1→3 (Fucα1→4) GlcNAcβ-OR as potential acceptors for a new member of the α-1,2-L-fucosyltransferase family

AU - Jain, Rakesh K.

AU - Pawar, Sushama M.

AU - Chandrasekaran, E. V.

AU - Piskorz, Conrad F.

AU - Matta, Khushi L.

PY - 1993/6

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N2 - A stereoselective synthesis of Galβ1→3 (Fucα1→4) GlcNAcβ-Or (Lewis a) structures containing an anomeric p-nitrophenyl or benzyl group was accomplished through the use of methyl 3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranosid e. The compounds were used as acceptors to show in human ovarian tumors and a colon carcinoma cell line (Colo 205), the presence of a new type of α1,2-L-fucosyltransferase which converts the blood group determinant Lewisa to Lewisb.

AB - A stereoselective synthesis of Galβ1→3 (Fucα1→4) GlcNAcβ-Or (Lewis a) structures containing an anomeric p-nitrophenyl or benzyl group was accomplished through the use of methyl 3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranosid e. The compounds were used as acceptors to show in human ovarian tumors and a colon carcinoma cell line (Colo 205), the presence of a new type of α1,2-L-fucosyltransferase which converts the blood group determinant Lewisa to Lewisb.

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M3 - Article

AN - SCOPUS:0027286236

SN - 0960-894X

VL - 3

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EP - 1338

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 6

ER -

Synthesis of Galβ1→3 (Fucα1→4) GlcNAcβ-OR as potential acceptors for a new member of the α-1,2-L-fucosyltransferase family

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