The antibody catalysis route to the total synthesis of epothilones.
An efficient monoclonal aldolase antibody that proceeds by an enamine mechanism was generated by reactive immunization. Here, this catalyst has been used in the total synthesis of epothilones A (1) and C (3). The starting materials for the synthesis of these molecules have been obtained by using antibody-catalyzed aldol and retro-aldol reactions. These precursors were then converted to epothilones A (1) and C (3) to complete the total synthesis.
Sinha
S C
SC
The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA. subhash@scripps.edu or ral@scripps.edu
Barbas
C F
CF
Lerner
R A
RA
D017151:Antibodies, Catalytic / Q000737:chemistry* / Q000276:immunology; D034261:Epothilones; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D005634:Fructose-Bisphosphate Aldolase / Q000737:chemistry / Q000276:immunology*; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry*
D017151:Antibodies, Catalytic; D034261:Epothilones; D004852:Epoxy Compounds; D013844:Thiazoles; C093787:epothilone A; D005634:Fructose-Bisphosphate Aldolase