title: Fluorescent glycosylamides produced by microscale derivatization of free glycans for natural glycan microarrays.
abstract: 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.
authors.affiliation: Department of Biochemistry, Emory University School of Medicine, Atlanta, Georgia 30322, USA.
authors.forename: Xuezheng
authors.initials: X
authors.lastname: Song
authors.forename: Yi
authors.initials: Y
authors.lastname: Lasanajak
authors.forename: Baoyun
authors.initials: B
authors.lastname: Xia
authors.forename: David F
authors.initials: DF
authors.lastname: Smith
authors.forename: Richard D
authors.initials: RD
authors.lastname: Cummings
mesh_terms: D000586:Amination; D000906:Antibodies / Q000032:analysis / Q000378:metabolism; D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D005456:Fluorescent Dyes / Q000032:analysis* / Q000378:metabolism; D037102:Lectins / Q000032:analysis / Q000378:metabolism; D008969:Molecular Sequence Data; D010084:Oxidation-Reduction; D011134:Polysaccharides / Q000032:analysis* / Q000378:metabolism; D040081:Protein Array Analysis / Q000295:instrumentation / Q000379:methods*; D011485:Protein Binding
chemical_list: D000906:Antibodies; D005456:Fluorescent Dyes; D037102:Lectins; D011134:Polysaccharides