Abstract
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 language | English |
---|---|
Pages (from-to) | 367-375 |
Number of pages | 9 |
Journal | Bioorganic and Medicinal Chemistry |
Volume | 6 |
Issue number | 4 |
DOIs | |
Publication status | Published - Apr 1998 |
Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry