Synthesis of artificial glycoconjugate polymers carrying 6-O-phosphocholine alpha-D-glucopyranoside, biologically active segment of main cell membrane glycolipids of Mycoplasma fermentans

As carbohydrate probes to investigate the biological activity of novel phos phocholine-containing glycoglycerolipids of M. fermentans, artificial glyco conjugate polymers carrying 6-O-phosphocholine alpha-D-glucopyranoside were synthesized. The synthesis involved a-selective 1-O-p-nitrophenylation (pN P) of 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose in the presence of a Lewis acid followed by the introduction of a phosphocholine group at pos ition O-6 by an amidite method. The pNP group was converted into ap -N-meth acrylamidophenyl group for subsequent radical polymerization.