Cyclodextrin-assisted Glycan Chain Extension on a Protected Glycosyl Amino Acid

6533b7d6fe1ef96bd126676f

RESEARCH PRODUCT

Cyclodextrin-assisted Glycan Chain Extension on a Protected Glycosyl Amino Acid

Andreas Liese Gregor Dudziak Nicole Bézay Horst Kunz Tilo Schwientek Henrik Clausen

subject

chemistry.chemical_classification Glycan Glycosylation biology Cyclodextrin Stereochemistry Organic Chemistry Biochemistry Amino acid carbohydrates (lipids)chemistry.chemical_compound chemistry Biosynthesis Yield (chemistry)Drug Discovery biology.protein Organic chemistry Glycosyl Solubility

description

By the use of cyclodextrins, we have enhanced the solubility of the protected amino acid glycan Fmoc-Thr(GalNAcα1)-OtBu (1b) up to 100-fold. This improvement enabled us to carry out an enzymatic glycosylation employing a β-galactosidase in combination with an α2,3-sialyltransferase without the aid of organic cosolvents. After optimization of the one-pot reaction, the sialylated core 1 structure Fmoc-Thr[Neu5Ac(α2-3)Gal(β1-3)GalNAcα1]-OtBu (3b) could be obtained with 50% yield.

year	journal	country	edition	language
2000-08-01	Tetrahedron

https://doi.org/10.1016/s0040-4020(00)00537-8

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