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. 2020 Jan 17;85(2):419-429.
doi: 10.1021/acs.joc.9b02420. Epub 2020 Jan 3.

A Mechanism-Based Sphingosine-1-phosphate Lyase Inhibitor

Guillem Pons  1 , Daniel Riba  1 , Mireia Casasampere  1   2 , Eduardo Izquierdo  1   2 , José-Luís Abad  1 , Gemma Fabriàs  1   3 , Pilar G Rodríguez Ortega  4 , Juan J López-González  4 , Manuel Montejo  4 , Josefina Casas  1   3 , Antonio Delgado  1   2
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A Mechanism-Based Sphingosine-1-phosphate Lyase Inhibitor

Guillem Pons et al. J Org Chem. .

Abstract

The synthesis of a series of vinylated analogues of sphingosine-1-phosphate together with their unambiguous configurational assignment by VCD methods is reported. Among them, compound RBM10-8 can irreversibly inhibit human sphingosine-1-phosphate lyase (hS1PL) while behaving also as an enzyme substrate. These findings, together with the postulated mechanism for S1PL activity, reinforce the role of RBM10-8 as a new mechanism-based hS1PL inhibitor.

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