Metampicillin is a cyclic aminal produced by reaction of ampicillin with formaldehyde.
Metampicillin is a cyclic aminal produced by reaction of ampicillin with formaldehyde.
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DOI：
10.1038/s41598-020-74990-1
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发表时间：
2020-10-21
影响因子：
4.6
通讯作者：
Hopkinson RJ
中科院分区：
文献类型：
--
作者：
Reinbold R;John T;Spingardi P;Kawamura A;Schofield CJ;Hopkinson RJ
氨苄西林是一种β-内酰胺类抗生素，由氨苄西林与甲醛反应而成。尽管美他西林已经被研究用于治疗动物和人类的感染，但它的结构一直不清楚。我们报告的核磁共振研究显示，美乃西林含有一种甲醛衍生的环胺。溶液中过量甲醛的核磁共振时间历程实验表明，与环氨基氮反应形成了另一个具有额外的外环半氨基的产物。环外半氨基很容易被甲醛清除剂1，3-环己二酮反应除去，而环氨基亚甲基表现出更大的稳定性。总体结果表明，甲氨苄西林的结构中含有环氨基，并进一步揭示了甲醛与生物医学相关分子反应的复杂性。
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.
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影响因子：
3.2
作者：
Shishodia S;Zhang D;El-Sagheer AH;Brown T;Claridge TDW;Schofield CJ;Hopkinson RJ
通讯作者：
Hopkinson RJ
影响因子：
3.2
作者：
Hopkinson, Richard J.;Barlow, Philippa S.;Claridge, Timothy D. W.
通讯作者：
Claridge, Timothy D. W.
影响因子：
3.3
作者：
SUTHERLAND, R;CROYDON, EAP;ELSON, S
通讯作者：
ELSON, S
影响因子：
5.2
作者：
BROGARD J M;PINGET M;LAVILLAUREIX J
通讯作者：
LAVILLAUREIX J
影响因子：
4.6
作者：
Reinbold, Raphael;John, Tobias;Hopkinson, Richard J.
通讯作者：
Hopkinson, Richard J.