Chemoenzymatic synthesis of heparan sulfate tetrasaccharide from a N-acetyl-α-D-glucosamine-O-methylglycoside acceptor

Xing Zhang; Demetria M. Dickinson; Lei Lin; Matthew Suflita; Sultan Baytas; Robert J. Linhardt

doi:10.1016/j.tetlet.2019.02.036

Chemoenzymatic synthesis of heparan sulfate tetrasaccharide from a N-acetyl-α-D-glucosamine-O-methylglycoside acceptor

Xing Zhang, Demetria M. Dickinson, Lei Lin, Matthew Suflita, Sultan Baytas, Robert J. Linhardt

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

7 Scopus citations

Abstract

Heparan sulfate tetrasaccharide 2 was efficiently prepared in seven steps through chemoenzymatic synthesis. A monosaccharide 5, N-acetyl-α-D-glucosamine- O-methylglycoside (GlcNAc-OMe), was successfully used as an acceptor in a heparosan synthase (pmHS2)-catalyzed glycosylation reaction. This avoided the multi-step synthesis of a more complex disaccharide acceptor 3, greatly simplifying the route to tetrasaccharide target 2. This approach provides a critical tetrasaccharide intermediate for subsequent chemoenzymatic transformation to fondaparinux and its analogues.

Original language	English
Pages (from-to)	911-915
Number of pages	5
Journal	Tetrahedron Letters
Volume	60
Issue number	13
DOIs	https://doi.org/10.1016/j.tetlet.2019.02.036
State	Published - 28 Mar 2019
Externally published	Yes

Keywords

Chemoenzymatic synthesis
Heparan sulfate
Heparin
Oligosaccharides, glycosylation

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10.1016/j.tetlet.2019.02.036

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title = "Chemoenzymatic synthesis of heparan sulfate tetrasaccharide from a N-acetyl-α-D-glucosamine-O-methylglycoside acceptor",

abstract = "Heparan sulfate tetrasaccharide 2 was efficiently prepared in seven steps through chemoenzymatic synthesis. A monosaccharide 5, N-acetyl-α-D-glucosamine- O-methylglycoside (GlcNAc-OMe), was successfully used as an acceptor in a heparosan synthase (pmHS2)-catalyzed glycosylation reaction. This avoided the multi-step synthesis of a more complex disaccharide acceptor 3, greatly simplifying the route to tetrasaccharide target 2. This approach provides a critical tetrasaccharide intermediate for subsequent chemoenzymatic transformation to fondaparinux and its analogues.",

keywords = "Chemoenzymatic synthesis, Heparan sulfate, Heparin, Oligosaccharides, glycosylation",

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doi = "10.1016/j.tetlet.2019.02.036",

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T1 - Chemoenzymatic synthesis of heparan sulfate tetrasaccharide from a N-acetyl-α-D-glucosamine-O-methylglycoside acceptor

AU - Zhang, Xing

AU - Dickinson, Demetria M.

AU - Lin, Lei

AU - Suflita, Matthew

AU - Baytas, Sultan

AU - Linhardt, Robert J.

PY - 2019/3/28

Y1 - 2019/3/28

N2 - Heparan sulfate tetrasaccharide 2 was efficiently prepared in seven steps through chemoenzymatic synthesis. A monosaccharide 5, N-acetyl-α-D-glucosamine- O-methylglycoside (GlcNAc-OMe), was successfully used as an acceptor in a heparosan synthase (pmHS2)-catalyzed glycosylation reaction. This avoided the multi-step synthesis of a more complex disaccharide acceptor 3, greatly simplifying the route to tetrasaccharide target 2. This approach provides a critical tetrasaccharide intermediate for subsequent chemoenzymatic transformation to fondaparinux and its analogues.

AB - Heparan sulfate tetrasaccharide 2 was efficiently prepared in seven steps through chemoenzymatic synthesis. A monosaccharide 5, N-acetyl-α-D-glucosamine- O-methylglycoside (GlcNAc-OMe), was successfully used as an acceptor in a heparosan synthase (pmHS2)-catalyzed glycosylation reaction. This avoided the multi-step synthesis of a more complex disaccharide acceptor 3, greatly simplifying the route to tetrasaccharide target 2. This approach provides a critical tetrasaccharide intermediate for subsequent chemoenzymatic transformation to fondaparinux and its analogues.

KW - Chemoenzymatic synthesis

KW - Heparan sulfate

KW - Heparin

KW - Oligosaccharides, glycosylation

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DO - 10.1016/j.tetlet.2019.02.036

M3 - Article

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SN - 0040-4039

VL - 60

SP - 911

EP - 915

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 13

ER -

Chemoenzymatic synthesis of heparan sulfate tetrasaccharide from a N-acetyl-α-D-glucosamine-O-methylglycoside acceptor

Abstract

Keywords

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