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Synlett 1996; 1996(5): 452-454
DOI: 10.1055/s-1996-5464
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Effective Synthesis of Four Isomeric Trehalose Dicorynomycolates (TDCMs) and Their Immunoadjuvant Activities

Mugio Nishizawa1 , Dulce M. García, Ryutaro Minagawa, Yohko Noguchi, Hiroshi Imagawa, Hidetoshi Yamada, Ryosuke Watanabe, Yung Choon Yoo, Ichiro Azuma2
  • 1Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima 770, Japan, Fax 81-886-55-3051; E-mail mugion@mandala.co.jp
  • 2Institute of Immunological Science, Hokkaido University, Sapporo 060, Japan, Fax 81-11-709-6482, E-mail i_azuma@imm.hokudai.ac.jp
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Publication Date:
31 December 2000 (online)

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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