ISSN:
0170-2041
Keywords:
Diazirines
;
Disaccharide-C-glycosides
;
C-Glycosides
;
Immunoglobulin A
;
Photoaffinity labelling
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
A Photolabile Disaccharide-C-glycoside as an Affinity Reagent for IgA X24By enzymatic β-galactosylation of 3,7-anhydro-2-azi-1,2-dideoxy-D-glycero-L-manno-octitol (2) with β-galactosidase from E. coli using o-nitrophenyl-β-D-galactopyranoside as donor the disaccharide-C-glycosides 8-O-(β-D-galactopyranosyl)- (7) and 3,7-anhydro-2-azi-1,2-dideoxy-5-O-(β-D-galactopyranosyl)-D-glycero-L-manno-octitol (9) were prepared and identified by 1H NMR. Compound 7 was also synthesized chemically. Whereas 2 and 9 showed no measurable affinity to the monoclonal antigalactan IgA X24, the binding constant for 7 was Ka = 0.96 × 104 [mol/1]-1 and therefore slightly better then the one for the ordinary disaccharide β-D-galactopyranosyl-(1→6)-D-galactose. Compound 7 is a very efficient photoaffinity label for IgA X24. Radioactive 7 was used to specifically modify the antibody preferentially in the heavy peptide chain.
Notes:
Neben anderen Übertragungsprodukten entstehen bei der Galactosylierung von 3,7-Anhydro-2-azi-1,2-didesoxy-D-glycero-L-manno-octitol (2) mit β-Galactosidase aus E. coli und o-Nitrophenyl-β-D-galactopyranosid als Donor die Disaccharid-C-glycoside 8-O-(β-D-Galactopyranosyl)- (7) und 3,7-Anhydro-2-azi-1,2-didesoxy-5-O-(β-D-galactopyranosyl)
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198919890161
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