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Chemoenzymatic Synthesis of Sialyl‐Trimeric‐Lewis X
Author(s) -
Koeller Kathryn M.,
Wong ChiHuey
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(20000403)6:7<1243::aid-chem1243>3.0.co;2-j
Subject(s) - fucose , chemistry , sialic acid , glycosylation , glycolipid , sialyl lewis x , glycosyltransferase , stereochemistry , glycoprotein , regioselectivity , fucosyltransferase , chemical synthesis , enzyme , biochemistry , selectin , catalysis , organic chemistry , adhesion , in vitro
The decasaccharide sialyl‐trimeric‐Lewis x is a component of glycoproteins and glycolipids that serve as E‐ and P‐selectin ligands. The synthesis of this target structure was accomplished by utilizing a combination of chemical and enzymatic methods. Highlights of the chemical synthesis include minimal use of protecting groups and regioselective glycosylations to arrive at a linear tri‐lactosamine structure. Glycosyltransferase‐catalyzed reactions were then employed for the addition of the terminal sialic acid and branch‐point fucose residues. Notably, fucosyltransferases V and VI showed different specificities for the sialyl‐tri‐lactosamine core structure.