Biology

Enzymatic kinetic resolution of desmethylphosphinothricin indicates that phosphinic group is a bioisostere of carboxyl group

D. D. Biase, F. Cappadocio, et al.

Discover how Escherichia coli glutamate decarboxylase (EcGadB) transforms a unique phosphinic analog of glutamate into a metabolite with promising implications for prodrug design. This fascinating research was conducted by Daniela De Biase, Francesca Cappadocio, Eugenia Pennacchietti, Fabio Giovannercole, Antonio Coluccia, Jouko Vepsäläinen, and Alex Khomutov.

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Abstract

This study demonstrates that Escherichia coli glutamate decarboxylase (EcGadB) effectively decarboxylates the L-isomer of D,L-2-amino-4-(hydroxyphosphinyl)butyric acid (D,L-Glu-γ-PH), a phosphinic analog of glutamate, yielding 3-aminopropylphosphinic acid (GABA-PH). The research further shows that GABA-PH is metabolized by GABase to 3-(hydroxyphosphinyl)propionic acid (Succinate-PH). These findings suggest that the phosphinic group is a bioisostere of the carboxyl group, opening possibilities for prodrug design.

Publisher

Communications Chemistry

Published On

Sep 02, 2020

Authors

Daniela De Biase, Francesca Cappadocio, Eugenia Pennacchietti, Fabio Giovannercole, Antonio Coluccia, Jouko Vepsäläinen, Alex Khomutov

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