[reaction: see text] Synthesis of glycosyl cyanides was optimized with a new catalyst system. Reduction of tri-O-acetyl-beta-L-fucopyranosyl cyanide with Pd-hydrogen, in the presence of Ac(2)O and Boc(2)O, gave N-protected-mono- and -di-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylmethyl)-amines, which allow for the syntheses of small cluster oligosaccharide mimetics of fucopyranosylomethyl-substituted ureas. From di-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylmethyl) amine was also prepared a carbamoyl chloride as a potentially useful synthon for preparation of more complex C-glycosidic conjugates.
Three different characterization methods-13 C NMR spectroscopy, a terminal terpolymerization model, and a probability analysis based on the Poisson distribution-were used to determine the microstructure of random terpolymers. The methods were used to determine the amino acid sequence distribution of random terpolymers prepared from the polymerization of N-carboxyanhydrides that contained L-leucine, b-benzyl-L-aspartate, and L-valine. Poly(L-leucine-L-aspartic acid-L-valine) [poly(LDV)] was designed as a target specific substrate for the a 4 b 1 integrin that recognizes the tripeptide sequence leucine-aspartic acid-valine (LDV). The presence of the tripeptide sequence LDV within the polymer was determined to be eight LDV triad sequences on average in terpolymers of approximately 100 kDa.
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