MISC

1997年7月

Structure-activity relationships of penem antibiotics: crystallographic structures and implications for their antimicrobial activities

Bioorganic and Medicinal Chemistry
  • Rie Tanaka
  • ,
  • Yoshiaki Oyama
  • ,
  • Seiichi Imajo
  • ,
  • Shinsuke Matsuki
  • ,
  • Masaji Ishiguro

5
7
開始ページ
1389
終了ページ
1399
記述言語
英語
掲載種別
DOI
10.1016/S0968-0896(97)00073-4

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.

リンク情報
DOI
https://doi.org/10.1016/S0968-0896(97)00073-4
PubMed
https://www.ncbi.nlm.nih.gov/pubmed/9377099
ID情報
  • DOI : 10.1016/S0968-0896(97)00073-4
  • ISSN : 0968-0896
  • PubMed ID : 9377099
  • SCOPUS ID : 0030861043

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