Synthesis of a simplified bryostatin C-ring analogue that binds to the CRD2 of human PKC-alpha and construction of a novel BC-analogue by an unusual Julia olefination process

Hale, K. J.; Frigerio, M.; Manaviazar, S.; Hummersone, M. G.; Fillingham, I. J.; Barsukov, I. G.; Damblon, Christian; Gescher, A.; Roberts, G. C. K.

doi:10.1021/ol027392u

Article (Scientific journals)

Synthesis of a simplified bryostatin C-ring analogue that binds to the CRD2 of human PKC-alpha and construction of a novel BC-analogue by an unusual Julia olefination process

Hale, K. J.; Frigerio, M.; Manaviazar, S. et al.

2003 • In Organic Letters, 5 (4), p. 499-502

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https://hdl.handle.net/2268/77941

DOI
10.1021/ol027392u

PubMed
12583753

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Abstract :

[en] [GRAPHICS] The synthesis of two truncated bryostatin analogues 2 and 3 is described. High-field NMR measurements on the C-ring analogue 3 in (CH3CN)-H-2 containing 25% (H2O)-H-2 have shown that it binds to the CRD2 of human PKC-alpha at virtually the same position as phorbol-13-acetate (PA) and bryostatin 1 (1). NMR titration studies have also revealed that 3 binds to the CRD2 with a potency similar in magnitude to PA but much less potently than 1.

Disciplines :

Chemistry

Author, co-author :

Hale, K. J.

Frigerio, M.

Manaviazar, S.

Hummersone, M. G.

Fillingham, I. J.

Barsukov, I. G.

Damblon, Christian ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie biologique structurale

Gescher, A.

Roberts, G. C. K.

Language :

English

Title :

Synthesis of a simplified bryostatin C-ring analogue that binds to the CRD2 of human PKC-alpha and construction of a novel BC-analogue by an unusual Julia olefination process

Publication date :

2003

Journal title :

Organic Letters

ISSN :

1523-7060

eISSN :

1523-7052

Publisher :

American Chemical Society

Volume :

Issue :

Pages :

499-502

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 27 November 2010

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