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Metampicillin is a Cyclic Aminal Produced by Reaction of Ampicillin With Formaldehyde

Lookup NU author(s): Professor Akane Kawamura

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This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).


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 metadata

Author(s): Reinbold R, John T, Spingardi P, Kawamura A, Schofield CJ, Hopkinson RJ

Publication type: Article

Publication status: Published

Journal: Scientific Reports

Year: 2020

Volume: 10

Online publication date: 21/10/2020

Acceptance date: 03/09/2020

Date deposited: 30/11/2020

ISSN (electronic): 2045-2322

Publisher: Nature Publishing Group

URL: https://doi.org/10.1038/s41598-020-74990-1

DOI: 10.1038/s41598-020-74990-1

PubMed id: 33087772


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Funding

Funder referenceFunder name
091857/7/10/7
Adolf-Haeuser foundation
BB/J001694/2
BB/L000121/1
BB/R506655/1
C8717/A18245
FRIAS
GlaxoSmithKline
EP/R512060/1
ERASMUS Placement
Oxford-GSK-Crick Doctoral Programme in Chemical Biology
Verband-der-Freunde-der-Universitaet-Freiburg foundation

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