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Glycoconjugate Journal 20, 107118, 2004 C 2004 Kluwer Academic Publishers. Manufactured in The Netherlands.
 

Summary: Glycoconjugate Journal 20, 107­118, 2004
C 2004 Kluwer Academic Publishers. Manufactured in The Netherlands.
Alpha-Galactosyl trisaccharide epitope:
Modification of the 6-primary positions and
recognition by human anti-Gal antibody
Peter R. Andreana, Przemyslaw Kowal, Adam J. Janczuk and Peng George Wang
Wayne State University, Detroit, MI 48202, USA
Galactose oxidase (EC 1.1.3.9, GAO) was used to convert the C-6 OH of Gal(1 4)Glc­OBn (5) to the corresponding
hydrated aldehyde (7). Chemical modification, through dehydratative coupling and reductive amination, gave rise to a small
library of Gal(1 4)Glc­OBn analogues (9a­f, 10, 11). UDP-[6-3
H]Gal studies indicated that 1,3-galactosyltransferase
recognized the C-6 modified Gal(1 4)Glc­OBn analogues (9a­f, 10, 11). Preparative scale reactions ensued, utilizing
a single enzyme UDP-Gal conversion as well as a dual enzymatic system (GalE and 1,3GalT), taking full advantage of the
more economical UDP-Glc, giving rise to compounds 6, 15­22. Gal(1 3)Gal(1 4)Glc­OBn trisaccharide (6) was
produced on a large scale (2 g) and subjected to the same chemoenzymatic modification as stated above to produce C-6
modified derivatives (23­30). An ELISA bioassay was performed utilizing human anti-Gal antibodies to study the binding
affinity of the derivatized epitopes (6, 15­30). Modifications made at the C-6 position did not alter the IgG antibody's
ability to recognize the unnatural epitopes. Modifications made at the C-6 position resulted in significant or complete
abrogation of recognition. The results indicate that the C-6 OH of the Gal trisaccharide epitope is not mandatory for
antibody recognition.

  

Source: Andreana, Peter R. - Department of Chemistry, Wayne State University

 

Collections: Chemistry