The first chemical synthesis of novel MeO-3-GlcUA derivative of hyaluronan-based disaccharide to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs)

Guohua Wei; Vip Kumar; Jun Xue; Robert D. Locke; Khushi L. Matta

doi:10.1016/j.tetlet.2009.09.042

The first chemical synthesis of novel MeO-3-GlcUA derivative of hyaluronan-based disaccharide to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs)

Guohua Wei
, Vip Kumar
, Jun Xue
, Robert D. Locke
, Khushi L. Matta

Department of Chemical and Biological Engineering

Roswell Park Cancer Institute
CAS - Research Center for Eco-Environmental Sciences

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

4 Scopus citations

Abstract

The first chemical synthesis of MeO-3-GlcUAp(1 →3)GlcNAc-UDP to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs) is described. Construction of the desired β(1 →3)-linked disaccharide 10 was achieved very efficiently by coupling MeO-3-GlcUA donor 3 with the suitable protected GlcNTroc acceptor 4 using BF₃Et₂O as Lewis acid. Chemoselective removal of anomeric NAP, phosphorylation, hydrogenation, coupling with UMP-morpholidate, and finally complete deprotection gave the target compound 1 in good yield.

Original language	English
Pages (from-to)	6543-6545
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	47
DOIs	https://doi.org/10.1016/j.tetlet.2009.09.042
State	Published - Nov 25 2009

Keywords

MeO-3-GlcUA Hyaluronic acid synthases (HASs) Oligosaccharides Phosphorylation

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10.1016/j.tetlet.2009.09.042

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title = "The first chemical synthesis of novel MeO-3-GlcUA derivative of hyaluronan-based disaccharide to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs)",

abstract = "The first chemical synthesis of MeO-3-GlcUAp(1 →3)GlcNAc-UDP to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs) is described. Construction of the desired β(1 →3)-linked disaccharide 10 was achieved very efficiently by coupling MeO-3-GlcUA donor 3 with the suitable protected GlcNTroc acceptor 4 using BF3Et2O as Lewis acid. Chemoselective removal of anomeric NAP, phosphorylation, hydrogenation, coupling with UMP-morpholidate, and finally complete deprotection gave the target compound 1 in good yield.",

keywords = "MeO-3-GlcUA Hyaluronic acid synthases (HASs) Oligosaccharides Phosphorylation",

author = "Guohua Wei and Vip Kumar and Jun Xue and Locke, \{Robert D.\} and Matta, \{Khushi L.\}",

year = "2009",

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T1 - The first chemical synthesis of novel MeO-3-GlcUA derivative of hyaluronan-based disaccharide to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs)

AU - Wei, Guohua

AU - Kumar, Vip

AU - Xue, Jun

AU - Locke, Robert D.

AU - Matta, Khushi L.

PY - 2009/11/25

Y1 - 2009/11/25

N2 - The first chemical synthesis of MeO-3-GlcUAp(1 →3)GlcNAc-UDP to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs) is described. Construction of the desired β(1 →3)-linked disaccharide 10 was achieved very efficiently by coupling MeO-3-GlcUA donor 3 with the suitable protected GlcNTroc acceptor 4 using BF3Et2O as Lewis acid. Chemoselective removal of anomeric NAP, phosphorylation, hydrogenation, coupling with UMP-morpholidate, and finally complete deprotection gave the target compound 1 in good yield.

AB - The first chemical synthesis of MeO-3-GlcUAp(1 →3)GlcNAc-UDP to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs) is described. Construction of the desired β(1 →3)-linked disaccharide 10 was achieved very efficiently by coupling MeO-3-GlcUA donor 3 with the suitable protected GlcNTroc acceptor 4 using BF3Et2O as Lewis acid. Chemoselective removal of anomeric NAP, phosphorylation, hydrogenation, coupling with UMP-morpholidate, and finally complete deprotection gave the target compound 1 in good yield.

KW - MeO-3-GlcUA Hyaluronic acid synthases (HASs) Oligosaccharides Phosphorylation

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DO - 10.1016/j.tetlet.2009.09.042

M3 - Article

AN - SCOPUS:78649852586

SN - 0040-4039

VL - 50

SP - 6543

EP - 6545

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 47

ER -

The first chemical synthesis of novel MeO-3-GlcUA derivative of hyaluronan-based disaccharide to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs)

Abstract

Keywords

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