Chemoenzymatic Synthesis of Keratan Sulfate Oligosaccharides Using UDP-Galactose-6-aldehyde To Control Sulfation at Galactosides

Yunfei Wu; Gerlof P. Bosman; Gaël M. Vos; Elif Uslu; Digantkumar Chapla; Chin Huang; Kelley W. Moremen; Geert-Jan Boons

doi:10.1021/acs.orglett.4c02899

Chemoenzymatic Synthesis of Keratan Sulfate Oligosaccharides Using UDP-Galactose-6-aldehyde To Control Sulfation at Galactosides

Yunfei Wu
, Gerlof P. Bosman
, Gaël M. Vos
, Elif Uslu
, Digantkumar Chapla
, Chin Huang
, Kelley W. Moremen
, Geert-Jan Boons^*

^*Corresponding author for this work

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

Abstract

Keratan sulfate (KS) is a highly complex proteoglycan that has a poly-LacNAc chain that can be modified by diverse patterns of sulfate esters at C-6 positions of galactoside (Gal) and N-acetylglucosamine (GlcNAc) residues. Here, a chemo-enzymatic methodology is described that can control the pattern of sulfation at Gal using UDP-Gal-aldehyde as a donor for poly-LacNAc assembly to temporarily block specific sites from sulfation by galactose 6-sulfotransferase (CHST1).

Original language	English
Pages (from-to)	8272–8277
Number of pages	6
Journal	Organic Letters
Volume	26
Issue number	39
Early online date	23 Sept 2024
DOIs	https://doi.org/10.1021/acs.orglett.4c02899
Publication status	Published - 2024

Bibliographical note

Publisher Copyright:
© 2024 The Authors. Published by American Chemical Society.

Funding

This research was supported by the European Commission (Grant 101020769 to Geert-Jan Boons) and the Chinese Scholarship Council (to Yunfei Wu).

Funders	Funder number
European Commission	101020769
Chinese Scholarship Council

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title = "Chemoenzymatic Synthesis of Keratan Sulfate Oligosaccharides Using UDP-Galactose-6-aldehyde To Control Sulfation at Galactosides",

abstract = "Keratan sulfate (KS) is a highly complex proteoglycan that has a poly-LacNAc chain that can be modified by diverse patterns of sulfate esters at C-6 positions of galactoside (Gal) and N-acetylglucosamine (GlcNAc) residues. Here, a chemo-enzymatic methodology is described that can control the pattern of sulfation at Gal using UDP-Gal-aldehyde as a donor for poly-LacNAc assembly to temporarily block specific sites from sulfation by galactose 6-sulfotransferase (CHST1).",

author = "Yunfei Wu and Bosman, \{Gerlof P.\} and Vos, \{Ga{\"e}l M.\} and Elif Uslu and Digantkumar Chapla and Chin Huang and Moremen, \{Kelley W.\} and Geert-Jan Boons",

note = "Publisher Copyright: {\textcopyright} 2024 The Authors. Published by American Chemical Society.",

year = "2024",

doi = "10.1021/acs.orglett.4c02899",

language = "English",

volume = "26",

pages = "8272–8277",

journal = "Organic Letters",

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TY - JOUR

T1 - Chemoenzymatic Synthesis of Keratan Sulfate Oligosaccharides Using UDP-Galactose-6-aldehyde To Control Sulfation at Galactosides

AU - Wu, Yunfei

AU - Bosman, Gerlof P.

AU - Vos, Gaël M.

AU - Uslu, Elif

AU - Chapla, Digantkumar

AU - Huang, Chin

AU - Moremen, Kelley W.

AU - Boons, Geert-Jan

PY - 2024

Y1 - 2024

N2 - Keratan sulfate (KS) is a highly complex proteoglycan that has a poly-LacNAc chain that can be modified by diverse patterns of sulfate esters at C-6 positions of galactoside (Gal) and N-acetylglucosamine (GlcNAc) residues. Here, a chemo-enzymatic methodology is described that can control the pattern of sulfation at Gal using UDP-Gal-aldehyde as a donor for poly-LacNAc assembly to temporarily block specific sites from sulfation by galactose 6-sulfotransferase (CHST1).

AB - Keratan sulfate (KS) is a highly complex proteoglycan that has a poly-LacNAc chain that can be modified by diverse patterns of sulfate esters at C-6 positions of galactoside (Gal) and N-acetylglucosamine (GlcNAc) residues. Here, a chemo-enzymatic methodology is described that can control the pattern of sulfation at Gal using UDP-Gal-aldehyde as a donor for poly-LacNAc assembly to temporarily block specific sites from sulfation by galactose 6-sulfotransferase (CHST1).

UR - https://www.scopus.com/pages/publications/85205740469

U2 - 10.1021/acs.orglett.4c02899

DO - 10.1021/acs.orglett.4c02899

M3 - Article

SN - 1523-7060

VL - 26

SP - 8272

EP - 8277

JO - Organic Letters

JF - Organic Letters

IS - 39

ER -

Chemoenzymatic Synthesis of Keratan Sulfate Oligosaccharides Using UDP-Galactose-6-aldehyde To Control Sulfation at Galactosides

Abstract

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