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. 2024 Oct 4;26(39):8272-8277.
doi: 10.1021/acs.orglett.4c02899. Epub 2024 Sep 23.

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

Yunfei Wu  1 , Gerlof P Bosman  1 , Gaël M Vos  1 , Elif Uslu  1 , Digantkumar Chapla  2 , Chin Huang  2   3 , Kelley W Moremen  2   3 , Geert-Jan Boons  1   2   4   5
Affiliations

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

Yunfei Wu et al. Org Lett. .

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).

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
KS structure and chemoenzymatic synthesis strategy. (a) KS are N- and O-glycans having a sulfated poly-LacNAc chain. (b) Previously developed stop-and-go strategy for selective sulfation of Gal by 2,6-sialylation. (c) New stop-and-go strategy for selective sulfation of Gal using UDP-Gal-6-aldehyde. (d) Legend of monosaccharide structures.
Scheme 1
Scheme 1. Synthesis of UDP-Gal-6-aldehyde 2 and Acceptor Properties
Scheme 2
Scheme 2. Enzymatic Synthesis of Selectively Sulfated KS Oligosaccharides [R = (CH2)5NHCbz]
Scheme 3
Scheme 3. Formal Synthesis of KS-Derived Oligosaccharide 18
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