JBC, Vol. 252, Issue 8, 2575-2579, Apr, 1977
Chemical synthesis of phosphorylated retinoids. Their mannosyl acceptor activity in rat liver membranes
L. M. De Luca, J. P. Frot-Coutaz, C. S. Silverman-Jones and P. R. Roller
Phosphorylated retinoids were synthesized by a modification of the
procedure that Popjak et al. (Popjak, G., Cornforth, J. W., Cornforth, R.
H., Ryhage, R., and Goodman, D. S. (1962) J. Biol. Chem. 237, 56-61) used
to synthesize farnesylpyrophosphate. The all-trans-beta-retinyl phosphate;
all-trans-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatet
raene-1-yl phosphate; perhydromonoeneretinyl phosphate;
all-trans-beta-retinoyl phosphate; 13-cis-beta-retinoyl phosphate
derivatives were tested as acceptors of [14C]mannose from GDP-[14C]mannose
in a reaction catalyzed by rat liver membranes. The phosphate esters all
functioned as acceptors of mannose to give a product chromatographically
indistinguishable from endogenous mannosylretinyl phosphate. The mixed
anhydrides, however, did not function as mannosyl acceptors. Neither class
of compounds had any effect on the biosynthesis of dolichylmannosyl
phosphate. Rat liver membranes did not catalyze the transfer of
[14C]galactose from UDP-[14C]galactose to retinyl phosphate even at a
concentration of retinyl phosphate (0.73 mM) which stimulated formation o
mannosylretinyl phosphate by more than 50-fold...
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