EPSP SYNTHASE INHIBITOR DESIGN .3. SYNTHESIS AND EVALUATION OF A NEW 5-OXAMIC ACID ANALOG OF EPSP WHICH INCORPORATES A MALONATE ETHER AS A 3-PHOSPHATE MIMIC

Authors
COREY SD PANSEGRAU PD WALKER MC SIKORSKI JA
Citation
Sd. Corey et al., EPSP SYNTHASE INHIBITOR DESIGN .3. SYNTHESIS AND EVALUATION OF A NEW 5-OXAMIC ACID ANALOG OF EPSP WHICH INCORPORATES A MALONATE ETHER AS A 3-PHOSPHATE MIMIC, Bioorganic & medicinal chemistry letters, 3(12), 1993, pp. 2857-2862
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
3
Issue
12
Year of publication
1993
Pages
2857 - 2862
Database
ISI
SICI code
0960-894X(1993)3:12<2857:ESID.S>2.0.ZU;2-I
Abstract
The unusual shikimate oxamic acid analog 3, containing a 3-malonate et her, was synthesized and found to be a potent product-analog inhibitor of EPSP synthase (K(i) = 5.2 +/- 0.2 muM). The potency of 3 confirms that these 3-malonate ethers function as effective 3-phosphate replace ments in this system and that the oxamic acid moiety represents an unu sual mimetic of the EPSP carboxyvinyl ether group.