Effective Synthesis of Four Isomeric Trehalose Dicorynomycolates (TDCMs) and Their Immunoadjuvant Activities
31 December 2000 (online)
Four stereoisomers of trehalose 6,6’-dicorynomycolate (TDCM) have been synthesized by using Noyori’s BINAP-Ru catalyzed asymmetric hydrogenation of a racemic β-ketolactone in very high diastereo- and enantio-selectivity as the key step. TDCM with RR fatty acid showed indistinguishable 1H NMR with that isolated from Corynebacterium matruchotii. Although all four stereoisomers of TDCM showed immunoadjuvant activity, natural RR TDCM as well as artificial SS TDCM showed significant activities.
TDCM - trehalose dicorynomycolate - immunoadjuvant activity - BINAP-Ru