A Mechanism-Based Sphingosine-1-phosphate Lyase Inhibitor

被引：6

作者：

Pons, Guillem ^{[1
]}

Riba, Daniel ^{[1
]}

Casasampere, Mireia ^{[1
,2
]}

Izquierdo, Eduardo ^{[1
,2
]}

Abad, Jose-Luis ^{[1
]}

Fabrias, Gemma ^{[1
,3
]}

Rodriguez Ortega, Pilar G. ^{[4
]}

Lopez-Gonzalez, Juan J. ^{[4
]}

Montejo, Manuel ^{[4
]}

Casas, Josefina ^{[1
,3
]}

Delgado, Antonio ^{[1
,2
]}

机构：

[1] CSIC, Inst Adv Chem Catalonia IQAC CSIC, Res Unit Bioact Mol RUBAM, Dept Biol Chem, Jordi Girona 18-26, Barcelona 08034, Spain

[2] Univ Barcelona, Fac Pharm, Dept Pharmacol Toxicol & Med Chem, Unit Pharmaceut Chem,CSIC, Avda Joan XXIII S-N, E-08028 Barcelona, Spain

[3] Ctr Invest Biomed Red CIBEREHD, Madrid 28029, Spain

[4] Univ Jaen, Fac Expt Sci, Dept Phys & Analyt Chem, Campus Lagunillas, Jaen 23071, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 02期

关键词：

ABSOLUTE-CONFIGURATION; SPHINGOSINE; PRODUCT; ADDUCTS; PROTEIN; ENZYME; SITE;

D O I：

10.1021/acs.joc.9b02420

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a series of vinylated analogues of sphingosine-l-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.

引用

页码：419 / 429

页数：11

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