Open AccessFluorescent Glycosylamides Produced by Microscale Derivatization of Free Glycans for Natural Glycan Microarrays
Author(s) -
Xuezheng Song,
Yi Lasanajak,
Baoyun Xia,
David F. Smith,
Richard D. Cummings
Publication year - 2009
Publication title -
acs chemical biology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.899
H-Index - 111
eISSN - 1554-8937
pISSN - 1554-8929
DOI - 10.1021/cb900067h
Subject(s) - glycan , reductive amination , acryloyl chloride , chemistry , fluorescence , pyranose , derivatization , monosaccharide , linker , biochemistry , combinatorial chemistry , sialic acid , hypochlorous acid , organic chemistry , chromatography , acrylate , mass spectrometry , polymer , physics , quantum mechanics , computer science , glycoprotein , operating system , catalysis , monomer
A novel strategy for creating naturally derived glycan microarrays has been developed. Glycosylamines are prepared from free reducing glycans and stabilized by reaction with acryloyl chloride to generate a glycosylamide in which the reducing monosaccharide has a closed-ring structure. Ozonolysis of the protected glycan yields an active aldehyde, to which a bifunctional fluorescent linker is coupled by reductive amination. The fluorescent derivatives are easily coupled through a residual primary alkylamine to generate glycan microarrays. This strategy preserves structural features of glycans required for antibody recognition and allows development of natural arrays of fluorescent glycans in which the cyclic pyranose structure of the reducing-end sugar residue is retained.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom