Beilstein J. Org. Chem.2012,8, 712–725, doi:10.3762/bjoc.8.80
modification of terminal galactose and N-acetylgalactosamine residues of poly-N-acetyllactosamine (poly-LacNAc) oligomers and N,N-diacetyllactosamine (LacDiNAc) by galactose oxidase. Product formation starting from different poly-LacNAc oligomers was characterised and optimised regarding formation of the C6
oligomers containing terminally and/or internally modified galactose residues were obtained, which can be used for binding studies and various other applications.
Keywords: chemo-enzymatic synthesis; galactose oxidase; glycosyltransferase; LacDiNAc; poly-N-acetyllactosamine; Introduction
N
-Acetyllactosamine (LacNAc; Galβ1,4GlcNAc) structures are important carriers of glycan epitopes, such as ABH or Lewis blood group determinants. Some of these are present on extended poly-N-acetyllactosamine glycans (poly-LacNAc; [Galβ1,4GlcNAc]n) which serve as spacers and additional information carriers [1][2][3][4
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Graphical Abstract
Scheme 1:
Reaction scheme of terminal galactose in poly-LacNAc-glycans (1a–d) or GalNAc in LacDiNAc (2) by ga...