Chemoenzymatic synthesis of heparin and heparan sulfate analogs
AssigneeThe Regents of the University of California
InventorsXi Chen, Hai Yu, Yanhong Li, Yi Chen, Jingyao Qu, Musleh M. Muthana, Kam Lau, Lars Bode
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Abstract
The present invention provides a one-pot multi-enzyme method for preparing UDP-sugars from simple sugar starting materials. The invention also provides a one-pot multi-enzyme method for preparing oligosaccharides from simple sugar starting materials.
Claims29
A method of synthesizing a UDP-sugar, the method comprising forming a reaction mixture comprising a first sugar, a nucleotide-sugar pyrophosphorylase, and a first enzyme selected from the group consisting of a kinase and a dehydrogenase, under conditions sufficient to form the UDP-sugar.
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A method of preparing an oligosaccharide, the method comprising:
- forming a first reaction mixture comprising a first sugar, an acceptor sugar, a glycosyltransferase, a nucleotide-sugar pyrophosphorylase, and an enzyme selected from a kinase and a dehydrogenase,
- under conditions sufficient to convert the first sugar to a UDP-sugar, and sufficient to couple the sugar in the UDP-sugar to the acceptor sugar,
- thereby preparing the oligosaccharide.
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A method of preparing a sialylated oligosaccharide having at least two sialic acid moieties, the method comprising forming a reaction mixture comprising:
- a substrate sugar,
- cytidine-5′-monophospho-sialic acid (CMP-sialic acid or CMP-Sia) or a derivative thereof, and
- Photobacterium damselae α2-6-sialyltransferase (Pd2,6ST)
- under conditions sufficient to form the sialylated oligosaccharide.
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A sialylated oligosaccharide selected from the group consisting of:
- Neu5Acα2-3(Neu5Acα2-6)Galβ1-4Glc;
- Neu5Acα2-8Neu5Acα2-3 Galβ1-4Glc;
- Neu5Acα2-3(Neu5Acα2-6)Galβ1-3GlcNAc;
- Neu5Acα2-6Galβ1-4GlcNAcβ1-3(Neu5Acα2-6)Galβ1-4Glc (DSLNnT);
- Neu5Acα2-6Galβ1-3GlcNAcβ1-3(Neu5Acα2-6)Galβ1-4Glc;
- and
- Neu5Acα2-3(Neu5Acα2-6)Galβ1-9KDN.
Dependencies are inferred from the claim text.