Journal article
Metampicillin is a cyclic aminal produced by reaction of ampicillin with formaldehyde
- Abstract:
- Metampicillin is a β-lactam antibiotic that is prepared by the reaction of ampicillin with formaldehyde. Although metampicillin has been studied for treatment of infections in animals and humans, its structure has been unclear. We report NMR studies revealing that metampicillin contains a formaldehyde-derived cyclic aminal. NMR time-course experiments with excess formaldehyde in solution show formation of another product with an additional exocyclic hemiaminal group formed by reaction with the cyclic aminal nitrogen. The exocyclic hemiaminal group is readily removed by reaction with the formaldehyde scavenger 1,3-cyclohexanedione, whereas the cyclic aminal methylene exhibits greater stability. The overall results assign the structure of metampicillin as containing a cyclic aminal and further reveal the potential for complexity in the reaction of formaldehyde with biomedicinally relevant molecules.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, 1.5MB, Terms of use)
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- Publisher copy:
- 10.1038/s41598-020-74990-1
Authors
+ Biotechnology and Biological Sciences Research Council
More from this funder
- Grant:
- BB/L004275/1
- BB/L000121/1
- Publisher:
- Nature Research
- Journal:
- Scientific Reports More from this journal
- Volume:
- 10
- Article number:
- 17955
- Publication date:
- 2020-10-21
- Acceptance date:
- 2020-09-03
- DOI:
- EISSN:
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2045-2322
- Language:
-
English
- Keywords:
- Pubs id:
-
1132751
- Local pid:
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pubs:1132751
- Deposit date:
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2020-09-18
Terms of use
- Copyright holder:
- Reinbold et al.
- Copyright date:
- 2020
- Rights statement:
- Copyright © 2020 The Author(s). This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.
- Licence:
- CC Attribution (CC BY)
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