Fast and easy synthesis of the non-commercially available standard isobutyl monophosphate (ammonium salt)

Wendy Escobedo-Hinojosa; Stephan C Hammer; Julian L Wissner; Bernhard Hauer

doi:10.1016/j.mex.2021.101455

Fast and easy synthesis of the non-commercially available standard isobutyl monophosphate (ammonium salt)

MethodsX. 2021 Jul 14:8:101455. doi: 10.1016/j.mex.2021.101455. eCollection 2021.

Authors

Wendy Escobedo-Hinojosa¹, Stephan C Hammer¹, Julian L Wissner¹, Bernhard Hauer¹

Affiliation

¹ Department of Technical Biochemistry, Institute of Biochemistry and Technical Biochemistry, University of Stuttgart, Stuttgart, Germany.

Abstract

In an attempt to establish a biosynthetic route towards isobutene, we faced the problem that the first intermediate isobutyl-monophosphate was not commercially available. In order to overcome this limitation we searched in the literature for protocols reporting the synthesis of phosphate monoesters from alcohols. Based on the suitability of the preceding developments for our purposes, we established a customized method for the fast, easy and affordable generation of the pursued molecule. Herein, a prompt and straightforward method for isobutyl-monophosphate (ammonium salt) is provided.•This is a customized method for the production of isobutyl-monophosphate (ammonium salt), using isobutanol as starting compound•Synthesis takes place in a one-pot fashion, under mild reaction conditions, in 2 h•The established sequential strategy requires 8 h at the most, including synthesis and purification steps to obtain the isolated product.

Keywords: 31P-NMR; Monophosphorylation; One-pot synthesis; Phosphate activation; Phosphate monoesters.