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The stereochemical requirement for protein kinase C activation by 3‐methyldiglycerides matches that found in naturally occurring tumor promoters aplysiatoxins
Author(s) -
Fanzuo Kong,
Yoshito Kishi,
Dolores PérezSala,
Robert R. Rando
Publication year - 1990
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(90)81364-t
Subject(s) - stereocenter , stereospecificity , diglyceride , stereochemistry , protein kinase a , chemistry , kinase , biochemistry , protein kinase c , biology , enzyme , enantioselective synthesis , catalysis
Protein kinase C is stereospecifically activated by, sn ‐1,2‐(S)‐diglycerides. A second chiral center was introduced into the diglycerides by preparing the 3‐methyl derivatives. The activation of protein kinase C was also stereospecific with respect to the new chiral center established at the C3 position of the methylated diglycerides. The stereospecificity of protein kinase C directed towards the C2 and C3 positions of the diglycerides is matched in the analogous C29 and C30 stereocenters of the tumor promoting debromoaplysiatoxins. This finding strengthens the view that the structurally diverse tumor promotors contain the embedded diglyceride‐like pharmacophore.