Synthesis of uridine 5′-diphosphoiduronic acid: A potential substrate for the chemoenzymatic synthesis of heparin

Michel Weïwer; Trevor Sherwood; Dixy E. Green; Miao Chen; Paul L. DeAngelis; Jian Liu; Robert J. Linhardt

doi:10.1021/jo801409c

Synthesis of uridine 5′-diphosphoiduronic acid: A potential substrate for the chemoenzymatic synthesis of heparin

Michel Weïwer, Trevor Sherwood, Dixy E. Green, Miao Chen, Paul L. DeAngelis, Jian Liu, Robert J. Linhardt

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

18 Scopus citations

Abstract

(Chemical Equation Presented) An improved understanding of the biological activities of heparin requires structurally defined heparin oligosaccharides. The chemoenzymatic synthesis of heparin oligosaccharides relies on glycosyltransferases that use UDP-sugar nucleotides as donors. Uridine 5′-diphosphoiduronic acid (UDP-IdoA) and uridine 5′- diphosphohexenuronic acid (UDP-HexUA) have been synthesized as potential analogues of uridine 5′-diphosphoglucuronic acid (UDP-GlcA) for enzymatic incorporation into heparin oligosaccharides. Non-natural UDP-IdoA and UDP-HexUA were tested as substrates for various glucuronosyltransferases to better understand enzyme specificity.

Original language	English
Pages (from-to)	7631-7637
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	73
Issue number	19
DOIs	https://doi.org/10.1021/jo801409c
State	Published - 3 Oct 2008
Externally published	Yes

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title = "Synthesis of uridine 5′-diphosphoiduronic acid: A potential substrate for the chemoenzymatic synthesis of heparin",

abstract = "(Chemical Equation Presented) An improved understanding of the biological activities of heparin requires structurally defined heparin oligosaccharides. The chemoenzymatic synthesis of heparin oligosaccharides relies on glycosyltransferases that use UDP-sugar nucleotides as donors. Uridine 5′-diphosphoiduronic acid (UDP-IdoA) and uridine 5′- diphosphohexenuronic acid (UDP-HexUA) have been synthesized as potential analogues of uridine 5′-diphosphoglucuronic acid (UDP-GlcA) for enzymatic incorporation into heparin oligosaccharides. Non-natural UDP-IdoA and UDP-HexUA were tested as substrates for various glucuronosyltransferases to better understand enzyme specificity.",

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T1 - Synthesis of uridine 5′-diphosphoiduronic acid

T2 - A potential substrate for the chemoenzymatic synthesis of heparin

AU - Weïwer, Michel

AU - Sherwood, Trevor

AU - Green, Dixy E.

AU - Chen, Miao

AU - DeAngelis, Paul L.

AU - Liu, Jian

AU - Linhardt, Robert J.

PY - 2008/10/3

Y1 - 2008/10/3

N2 - (Chemical Equation Presented) An improved understanding of the biological activities of heparin requires structurally defined heparin oligosaccharides. The chemoenzymatic synthesis of heparin oligosaccharides relies on glycosyltransferases that use UDP-sugar nucleotides as donors. Uridine 5′-diphosphoiduronic acid (UDP-IdoA) and uridine 5′- diphosphohexenuronic acid (UDP-HexUA) have been synthesized as potential analogues of uridine 5′-diphosphoglucuronic acid (UDP-GlcA) for enzymatic incorporation into heparin oligosaccharides. Non-natural UDP-IdoA and UDP-HexUA were tested as substrates for various glucuronosyltransferases to better understand enzyme specificity.

AB - (Chemical Equation Presented) An improved understanding of the biological activities of heparin requires structurally defined heparin oligosaccharides. The chemoenzymatic synthesis of heparin oligosaccharides relies on glycosyltransferases that use UDP-sugar nucleotides as donors. Uridine 5′-diphosphoiduronic acid (UDP-IdoA) and uridine 5′- diphosphohexenuronic acid (UDP-HexUA) have been synthesized as potential analogues of uridine 5′-diphosphoglucuronic acid (UDP-GlcA) for enzymatic incorporation into heparin oligosaccharides. Non-natural UDP-IdoA and UDP-HexUA were tested as substrates for various glucuronosyltransferases to better understand enzyme specificity.

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Synthesis of uridine 5′-diphosphoiduronic acid: A potential substrate for the chemoenzymatic synthesis of heparin

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