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Carbohydrate Research 337 (2002) 12471259 www.elsevier.com/locate/carres

Summary: Carbohydrate Research 337 (2002) 12471259
The synthesis of deoxy-a-Gal epitope derivatives for the evaluation
of an anti-a-Gal antibody binding
Adam J. Janczuk, Wei Zhang, Peter R. Andreana, Joshua Warrick, Peng G. Wang*
Department of Chemistry, Wayne State Uni6ersity, Detroit, MI 48202, USA
Received 6 March 2002; accepted 16 June 2002
a-Gal epitopes (also termed as a-Gal) are carbohydrate structures bearing the a-D-Gal-(13)-b-D-Gal terminus 1 and are
known to be the antigen responsible for antibody-mediated hyperacute rejection in xenotransplantation. Terminal 2-, 3-, 4-, and
6-deoxy-Gal derivatives of a-Gal were synthesized. Inhibition ELISA using mouse laminin was established to determine the
binding affinity of the synthesized a-Gal derivatives. 4-Deoxy-a-Gal derivative 7 showed a significant reduction in antibody
recognition. The IC50 value was 15-fold poorer than the standard a-Gal epitopes a-D-Gal-(13)-b-D-Gal-(14)-b-D-Glc-NHAc
(39) and a-D-Gal-(13)-b-D-Gal-(14)-b-D-Glc-OBn (40). A similar observation was seen with 2-deoxy-a-Gal derivative 5,
whose IC50 value was nearly tenfold higher than the standards. Interestingly, substitution at the terminal 3-position resulted in
only a fourfold decrease in antibody recognition, suggesting a possible point of future derivation. Finally, 6-deoxy-a-Gal
derivative 8 exhibited similar antibody recognition to both a-Gal epitope 39 and a-Gal epitope 40. This strongly suggests that
derivatization at the 6-position can be accomplished without loss of antibody recognition. These findings can be utilized for the
future design of other a-Gal derivatives. 2002 Elsevier Science Ltd. All rights reserved.
Keywords: a-Gal epitope; Deoxy sugars; Xenotransplantation; Anti-a-Gal antibody


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


Collections: Chemistry