EFFECTIVE SYNTHESIS OF 4 ISOMERIC TREHALOSE DICORYNOMYCOLATES (TDCMS)AND THEIR IMMUNOADJUVANT ACTIVITIES

Authors
NISHIZAWA M GARCIA DM MINAGAWA R NOGUCHI Y IMAGAWA H YAMADA H WATANABE R YOO YC AZUMA I
Citation
M. Nishizawa et al., EFFECTIVE SYNTHESIS OF 4 ISOMERIC TREHALOSE DICORYNOMYCOLATES (TDCMS)AND THEIR IMMUNOADJUVANT ACTIVITIES, Synlett, (5), 1996, pp. 452
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
5
Year of publication
1996
Database
ISI
SICI code
0936-5214(1996):5<452:ESO4IT>2.0.ZU;2-6
Abstract
Four stereoisomers of trehalose 6,6'-dicorynomycolate (TDCM) have been synthesized by using Noyori's BINAP-Ru catalyzed asymmetric hydrogena tion of a racemic beta-ketolactone in very high diastereo- and enantio -selectivity as the key step. TDCM with RR fatty acid showed indisting uishable H-1 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 act ivities.