Structural comparison of 1β-methylcarbapenem, carbapenem and penem: NMR studies and theoretical calculations

Tamiki Nishimura, Jun etsu Igarashi, Akira Sasaki, Makoto Sunagawa

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Structural comparisons of meropenem (1), desmethyl meropenem (2) and the penem analogue (3) which contain the same side chains at both C-2 and C-6 were performed using 1H NMR measurements together with 3-21G level of ab initio MO and molecular mechanics calculations. The ab initio MO calculations reproduced the skeletons of these strained β-lactam rings in good agreement with the crystallographic data. 1H NMR measurements in aqueous solution together with molecular modeling studies indicated that there were conformational differences of the C-2 and C-6 side chains in this series of compounds. These observations suggested that the conformational differences could affect their biological activities.

Original languageEnglish
Pages (from-to)367-375
Number of pages9
JournalBioorganic and Medicinal Chemistry
Issue number4
Publication statusPublished - Apr 1 1998
Externally publishedYes


All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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