Synthesis and photolytic activation of 6''-O-2-nitrobenzyl uridine-5'-diphosphogalactose: a 'caged' UDP-Gal derivative.
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.
Mannerstedt
Karin
K
Carlsberg Laboratory, Gamle Carlsberg Vej 10, Valby, Copenhagen, Denmark.
Hindsgaul
Ole
O
D000117:Acetylglucosamine / Q000737:chemistry; D000606:Amino Sugars / Q000737:chemistry; D015394:Molecular Structure; D009237:N-Acetyllactosamine Synthase / Q000737:chemistry; D009578:Nitrobenzenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D010782:Photolysis; D021241:Spectrometry, Mass, Electrospray Ionization; D014466:Ultraviolet Rays; D014531:Uridine Diphosphate Galactose / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D014539:Uridine Diphosphate Sugars / Q000138:chemical synthesis / Q000737:chemistry*
C529224:6''-O-2-nitrobenzyl uridine-5'-diphosphogalactose; D000606:Amino Sugars; D009578:Nitrobenzenes; D014539:Uridine Diphosphate Sugars; D014531:Uridine Diphosphate Galactose; C000458:N-acetyllactosamine; D009237:N-Acetyllactosamine Synthase; D000117:Acetylglucosamine