Total synthesis of azumamide A and azumamide E, evaluation as histone deacetylase inhibitors, and design of a more potent analogue
Total synthesis of azumamide A and azumamide E, evaluation as histone deacetylase inhibitors, and design of a more potent analogue
The unprecedented diastereoselective Mannich reaction of a Z-allylsulfoximine was a key step in the total synthesis of the marine natural products azumamide A and E, and an unnatural analogue. Their relative potency as histone deacetylase inhibitors was evaluated and found to correlate with predicted zinc-binding affinity.
cyclic tetrapeptides, asymmetric-synthesis, spiruchostatin-a
1105-1108
Wen, S.J.
75be9329-c03f-4510-96f8-715fd458e980
Carey, K.L.
7059c804-fa72-4839-a274-4b08718d4aac
Nakao, Y.
8c2a5b95-4120-4220-83a1-b46d506ecf64
Fusetani, N.
af190e7b-aa75-4194-a655-97102ed496df
Packham, G.
86855c5b-6b61-4367-b14b-c2fc2ba2ed11
Ganesan, A.
62aa5a87-9308-4383-8686-99726b6bcfb9
2007
Wen, S.J.
75be9329-c03f-4510-96f8-715fd458e980
Carey, K.L.
7059c804-fa72-4839-a274-4b08718d4aac
Nakao, Y.
8c2a5b95-4120-4220-83a1-b46d506ecf64
Fusetani, N.
af190e7b-aa75-4194-a655-97102ed496df
Packham, G.
86855c5b-6b61-4367-b14b-c2fc2ba2ed11
Ganesan, A.
62aa5a87-9308-4383-8686-99726b6bcfb9
Wen, S.J., Carey, K.L., Nakao, Y., Fusetani, N., Packham, G. and Ganesan, A.
(2007)
Total synthesis of azumamide A and azumamide E, evaluation as histone deacetylase inhibitors, and design of a more potent analogue.
Organic Letters, 9 (6), .
(doi:10.1002/chin.200731169).
Abstract
The unprecedented diastereoselective Mannich reaction of a Z-allylsulfoximine was a key step in the total synthesis of the marine natural products azumamide A and E, and an unnatural analogue. Their relative potency as histone deacetylase inhibitors was evaluated and found to correlate with predicted zinc-binding affinity.
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Published date: 2007
Keywords:
cyclic tetrapeptides, asymmetric-synthesis, spiruchostatin-a
Identifiers
Local EPrints ID: 54405
URI: http://eprints.soton.ac.uk/id/eprint/54405
ISSN: 1523-7060
PURE UUID: a6b534bb-b20e-4ae8-a1e1-434b2b60c377
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Date deposited: 31 Jul 2008
Last modified: 15 Mar 2024 10:47
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Contributors
Author:
S.J. Wen
Author:
K.L. Carey
Author:
Y. Nakao
Author:
N. Fusetani
Author:
G. Packham
Author:
A. Ganesan
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