Synthesis of Optically Pure Norcantharidin Analogue NCA‐01, a Highly Selective Protein Phosphatase 2B Inhibitor, and its Derivatives | Zendy

Shimizu  Tadashi | Zendy; Iizuka Masato | Zendy; Matsukura Hiroko | Zendy; Hashizume Daisuke | Zendy; Sodeoka Mikiko | Zendy

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Synthesis of Optically Pure Norcantharidin Analogue NCA‐01, a Highly Selective Protein Phosphatase 2B Inhibitor, and its Derivatives

Author(s) -

Shimizu Tadashi,

Iizuka Masato,

Matsukura Hiroko,

Hashizume Daisuke,

Sodeoka Mikiko

Publication year - 2012

Publication title -

chemistry – an asian journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.18

H-Index - 106

eISSN - 1861-471X

pISSN - 1861-4728

DOI - 10.1002/asia.201200077

Subject(s) - enantiomer , chemistry , jurkat cells , phosphatase , stereochemistry , optically active , enantiomeric excess , combinatorial chemistry , organic chemistry , enzyme , enantioselective synthesis , catalysis , immune system , t cell , immunology , biology

An efficient synthetic route to optically pure norcantharidin analogue NCA‐01, a highly selective inhibitor of protein phosphatase 2B (PP2B; calcineurin), has been developed. The absolute stereochemistry of the enantiomers was determined by X‐ray crystallographic analysis. Optically pure NCA derivatives that had various substituents at the C1 position were synthesized in a similar manner. The PP2B‐inhibitory activities of NCA‐01 and its derivatives were independent of the enantiomeric form. NCA‐01 dimethyl ester potently inhibited IL‐2 production in Jurkat cells.

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