Bioorganic and Medicinal Chemistry p. 1389 - 1399 (1997)
Update date:2022-08-04
Topics:
Tanaka, Rie
Oyama, Yoshiaki
Imajo, Seiichi
Matsuki, Shinsuke
Ishiguro, Masaji
Twelve closely related crystal structures of the penem derivatives revealed a characteristic short contact of the oxygen atom in the C2 side-chains with the S1 atom. The side-chain conformations of the crystal structures showed a good correlation with the antimicrobial activity. In particular, the penems which show high antimicrobial activity have similar torsion angles for S1-C2-C1'-C2', suggesting that the disposition of the C2' atom would be important for binding to penicillin-interacting enzymes. Two conformations of the C6 hydroxyethyl group were observed in the crystal structures. Of those two, the conformation with a larger torsion angle (δ = 179.2°) is deduced to be the enzyme-bound conformation in the Michaelis complex.
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