401. Synthesis and photolytic activation of 6''-O-2-nitrobenzyl uridine-5'-diphosphogalactose: a 'caged' UDP-Gal derivative.
- Author
-
Mannerstedt K and Hindsgaul O
- Subjects
- Acetylglucosamine chemistry, Amino Sugars chemistry, Molecular Structure, N-Acetyllactosamine Synthase chemistry, Nitrobenzenes chemical synthesis, Nitrobenzenes radiation effects, Spectrometry, Mass, Electrospray Ionization, Ultraviolet Rays, Uridine Diphosphate Galactose chemical synthesis, Uridine Diphosphate Galactose radiation effects, Uridine Diphosphate Sugars chemical synthesis, Nitrobenzenes chemistry, Photolysis, Uridine Diphosphate Galactose chemistry, Uridine Diphosphate Sugars chemistry
- Abstract
Placing an 2-nitrobenzyl group on O-6 of the galactosyl residue in uridine-5'-diphosphogalactose (UDP-Gal) gives 6''-O-2-nitrobenzyl-UDP-Gal that is shown to be inactive as a donor substrate for beta-(1-->4)-galactosyltransferase (GalT). On irradiation at 365 nm, the nitrobenzyl group is completely removed yielding native UDP-Gal that then transfers normally to produce the expected betaGal-(1-->4)-betaGlcNAc disaccharidic linkage. 6''-O-2-Nitrobenzyl-UDP-Gal thus fulfils the minimum requirements of a 'caged' UDP-Gal for application in time-resolved crystallographic studies of beta-(1-->4)-GalT.
- Published
- 2008
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