New simplified inhibitors of EPSP synthase: The importance of ring size for recognition at the shikimate 3-phosphate site

✍ Scribed by Mark L. Peterson; Susan D. Corey; Jose L. Font; Mark C. Walker; James A. Sikorski

• Book ID: 104364673
• Publisher: Elsevier Science
• Year: 1996
• Tongue: English
• Weight: 291 KB
• Volume: 6
• Category: Article
• ISSN: 0960-894X
• DOI: 10.1016/s0960-894x(96)00527-6

✦ Synopsis

The simple 4-[(a-hydroxy)phosphonomethyl]-lH-pyrrole-2-carboxylate 4 is a surprisingly good S3Panalog inhibitor of EPSP synthase (competitive with S3P, Ki(app) = 14.5 + 0.7 laM). The affinity of 4 for free enzyme is nearly comparable to that of S3P (K d = 7 + 1.2 IxM). Compound 4 thus represents the first successful attempt to replace the highly substituted shikimate ring in S3P with a readily accessible heterocyclic scaffold.