Synthesis of a bisubstrate-type inhibitor of N- acetylglucosaminyltransferases

Shinya Hanashima; Shino Manabe; Kei Ichiro Inamori; Naoyuki Taniguchi; Yukishige Ito

doi:10.1002/anie.200460388

Synthesis of a bisubstrate-type inhibitor of N- acetylglucosaminyltransferases

Shinya Hanashima, Shino Manabe, Kei Ichiro Inamori, Naoyuki Taniguchi, Yukishige Ito

PHA - Graduate School of Pharmaceutical Sciences (department affiliation only)

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

23 Citations (Scopus)

Abstract

Transfer interference: Synthesis of the bisubstrate-type N-acetylglucosaminyltransferase (GnT) inhibitor 1 was achieved by a polymer-resin hybrid capture-release strategy for the construction of the acceptor component. One-pot ligation in aqueous media produced the coupling product, and subsequent construction of a diphosphate linkage led to 1. Inhibitory activities toward GnT-V and GnT-IX were evaluated and revealed the potency of 1 toward the latter enzyme.

Original language	English
Pages (from-to)	5674-5677
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	43
Issue number	42
DOIs	https://doi.org/10.1002/anie.200460388
Publication status	Published - 2004 Oct 25

Keywords

Bisubstrates
Glycoproteins
Inhibitors
Solid-phase synthesis
Transferases

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10.1002/anie.200460388

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abstract = "Transfer interference: Synthesis of the bisubstrate-type N-acetylglucosaminyltransferase (GnT) inhibitor 1 was achieved by a polymer-resin hybrid capture-release strategy for the construction of the acceptor component. One-pot ligation in aqueous media produced the coupling product, and subsequent construction of a diphosphate linkage led to 1. Inhibitory activities toward GnT-V and GnT-IX were evaluated and revealed the potency of 1 toward the latter enzyme.",

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AU - Hanashima, Shinya

AU - Manabe, Shino

AU - Inamori, Kei Ichiro

AU - Taniguchi, Naoyuki

AU - Ito, Yukishige

PY - 2004/10/25

Y1 - 2004/10/25

N2 - Transfer interference: Synthesis of the bisubstrate-type N-acetylglucosaminyltransferase (GnT) inhibitor 1 was achieved by a polymer-resin hybrid capture-release strategy for the construction of the acceptor component. One-pot ligation in aqueous media produced the coupling product, and subsequent construction of a diphosphate linkage led to 1. Inhibitory activities toward GnT-V and GnT-IX were evaluated and revealed the potency of 1 toward the latter enzyme.

AB - Transfer interference: Synthesis of the bisubstrate-type N-acetylglucosaminyltransferase (GnT) inhibitor 1 was achieved by a polymer-resin hybrid capture-release strategy for the construction of the acceptor component. One-pot ligation in aqueous media produced the coupling product, and subsequent construction of a diphosphate linkage led to 1. Inhibitory activities toward GnT-V and GnT-IX were evaluated and revealed the potency of 1 toward the latter enzyme.

KW - Bisubstrates

KW - Glycoproteins

KW - Inhibitors

KW - Solid-phase synthesis

KW - Transferases

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Synthesis of a bisubstrate-type inhibitor of N- acetylglucosaminyltransferases

Abstract

Keywords

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