SYNTHETIC STUDY ON LIPOTEICHOIC ACID OF GRAM-POSITIVE BACTERIA .1. SYNTHESIS OF PROPOSED FUNDAMENTAL STRUCTURE OF STREPTOCOCCUS-PYOGENES LIPOTEICHOIC ACID

Synthetic study on Streptococcus pyogenes lipoteichoic acid (LTA) which was reported to induce nontoxic TNF is described. The proposed fundamental structure of LTA was constructed by coupling of the glycolipid part with the poly(glycerol phosphate) (PGP) part and subsequent deprotection. The PGP part was prepared by a simple repeating procedure using the phosphoramidite method for the construction of 1,3-phosphodiester-linkage. The glycolipid part was synthesized using appropriate glycosyl fluorides as donors, where the p-nitrobenzyl group was successfully applied to temporary protection of a hydroxyl function.