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Gary Keck

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Organization: University of Utah
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Title:
The Bryostatin 1 A-Ring Acetate is Not the Critical Determinant for Antagonism of Phorbol Ester-Induced Biological Responses
Co-reporter:Gary E. Keck, Wei Li, Matthew B. Kraft, Noemi Kedei, Nancy E. Lewin and Peter M. Blumberg
Organic Letters 2009 Volume 11(Issue 11) pp:2277-2280
Publication Date(Web):May 6, 2009
DOI:10.1021/ol900585t
The contribution of the A-ring C7 acetate to the function of bryostatin 1 has been investigated through synthesis and biological evaluation of an analogue incorporating this feature into the bryopyran core structure. No enhanced binding affinity for protein kinase C (PKC) was observed, relative to previously characterized analogues lacking the C7 acetate. Functional assays showed biological responses characteristic of those induced by the phorbol ester PMA and distinctly different from those observed with bryostatin 1.
CAS:1207107-74-1
Conventional protein kinase C
Conventional protein kinase C
CAS:141436-78-4
Conventional protein kinase C
5H-Cyclopropa[3,4]benz[1,2-e]azulen-5-one,1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-,(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-
5H-Cyclopropa[3,4]benz[1,2-e]azulen-5-one,1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-,(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-
CAS:17673-25-5
5H-Cyclopropa[3,4]benz[1,2-e]azulen-5-one,1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-,(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-
BRYOSTATIN 1;(1S,3S,5Z,7R,8E,11S,12S,13E,15S,17R,21R,23R,25S)-25-(ACETYLOXY)-1,11,21-TRIHYDROXY-17-[(1R)-1-HYDROXYETHYL]-5,13-BIS(2-METHOXY-2-OXOETHYLIDENE)-10,10,26,26-TETRAMETHYL-19-OXO-18,27,28,29-TETRAOXATETRACYCLO[21.3.1.13,7.111,15]NONACOS-8-EN-12-Y
BRYOSTATIN 1;(1S,3S,5Z,7R,8E,11S,12S,13E,15S,17R,21R,23R,25S)-25-(ACETYLOXY)-1,11,21-TRIHYDROXY-17-[(1R)-1-HYDROXYETHYL]-5,13-BIS(2-METHOXY-2-OXOETHYLIDENE)-10,10,26,26-TETRAMETHYL-19-OXO-18,27,28,29-TETRAOXATETRACYCLO[21.3.1.13,7.111,15]NONACOS-8-EN-12-Y
CAS:83314-01-6
BRYOSTATIN 1;(1S,3S,5Z,7R,8E,11S,12S,13E,15S,17R,21R,23R,25S)-25-(ACETYLOXY)-1,11,21-TRIHYDROXY-17-[(1R)-1-HYDROXYETHYL]-5,13-BIS(2-METHOXY-2-OXOETHYLIDENE)-10,10,26,26-TETRAMETHYL-19-OXO-18,27,28,29-TETRAOXATETRACYCLO[21.3.1.13,7.111,15]NONACOS-8-EN-12-Y