Synthesis of a new transition-state analog of the sialyl donor. Inhibition of sialyltransferases

Hongbin Sun; Jingsong Yang; Katie E. Amaral; Benjamin A. Horenstein

doi:10.1016/S0040-4039(01)00204-0

Synthesis of a new transition-state analog of the sialyl donor. Inhibition of sialyltransferases

Hongbin Sun, Jingsong Yang, Katie E. Amaral, Benjamin A. Horenstein

Division of Science (Berks)

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

32 Scopus citations

Abstract

A new class of glycosyltransferase inhibitor has been designed and synthesized. The designed inhibitors 3a/3b provide conformational mimicry of the transition state in sialyltransfer reactions. The key synthetic steps involve a Meinwald rearrangement and a palladium-catalyzed carbonylation reaction. The results of kinetic studies show that 3a/3b exhibit significant inhibition on both 2,3- and 2,6-sialytransferases.

Original language	English (US)
Pages (from-to)	2451-2453
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	13
DOIs	https://doi.org/10.1016/S0040-4039(01)00204-0
State	Published - Mar 26 2001

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Synthesis of a new transition-state analog of the sialyl donor. Inhibition of sialyltransferases",

abstract = "A new class of glycosyltransferase inhibitor has been designed and synthesized. The designed inhibitors 3a/3b provide conformational mimicry of the transition state in sialyltransfer reactions. The key synthetic steps involve a Meinwald rearrangement and a palladium-catalyzed carbonylation reaction. The results of kinetic studies show that 3a/3b exhibit significant inhibition on both 2,3- and 2,6-sialytransferases.",

author = "Hongbin Sun and Jingsong Yang and Amaral, {Katie E.} and Horenstein, {Benjamin A.}",

note = "Funding Information: We wish to thank the University of Florida and National Science Foundation (CAREER Award MCB-9501866 to B.A.H.) for this work. ",

year = "2001",

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doi = "10.1016/S0040-4039(01)00204-0",

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T1 - Synthesis of a new transition-state analog of the sialyl donor. Inhibition of sialyltransferases

AU - Sun, Hongbin

AU - Yang, Jingsong

AU - Amaral, Katie E.

AU - Horenstein, Benjamin A.

N1 - Funding Information: We wish to thank the University of Florida and National Science Foundation (CAREER Award MCB-9501866 to B.A.H.) for this work.

PY - 2001/3/26

Y1 - 2001/3/26

N2 - A new class of glycosyltransferase inhibitor has been designed and synthesized. The designed inhibitors 3a/3b provide conformational mimicry of the transition state in sialyltransfer reactions. The key synthetic steps involve a Meinwald rearrangement and a palladium-catalyzed carbonylation reaction. The results of kinetic studies show that 3a/3b exhibit significant inhibition on both 2,3- and 2,6-sialytransferases.

AB - A new class of glycosyltransferase inhibitor has been designed and synthesized. The designed inhibitors 3a/3b provide conformational mimicry of the transition state in sialyltransfer reactions. The key synthetic steps involve a Meinwald rearrangement and a palladium-catalyzed carbonylation reaction. The results of kinetic studies show that 3a/3b exhibit significant inhibition on both 2,3- and 2,6-sialytransferases.

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U2 - 10.1016/S0040-4039(01)00204-0

DO - 10.1016/S0040-4039(01)00204-0

M3 - Article

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VL - 42

SP - 2451

EP - 2453

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 13

ER -

Synthesis of a new transition-state analog of the sialyl donor. Inhibition of sialyltransferases

Abstract

All Science Journal Classification (ASJC) codes

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