Bioorganic and Medicinal Chemistry Letters p. 2853 - 2858 (1996)
Update date:2022-07-31
Topics:
Peterson, Mark L.
Corey, Susan D.
Font, Jose L.
Walker, Mark C.
Sikorski, James A.
The simple 4-[(α-hydroxy)phosphonomethyl]-1H-pyrrole-2-carboxylate 4 is a surprisingly good S3P-analog inhibitor of EPSP synthase (competitive with S3P, K(i(app)) = 14.5 ± 0.7 μM). The affinity of 4 for free enzyme is nearly comparable to that of S3P (K(d) = 7 ± 1.2 μM). Compound 4 thus represents the first successful attempt to replace the highly substituted shikimate ring in S3P with a readily accessible heterocyclic scaffold.
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