Enolphosphonate analogues of Cyclophostin. Fusarium solani cutinase was highly diastereoselective for the (Sp) configuration using (Sc) inhibitors, whereas no obvious stereopreference at phosphorus was observed with (Rc) compounds. Rv0183 from Mycobacterium tuberculosis exhibited strong enantioselective discrimination for (Sp) configuration regardless of the chirality at the asymmetric carbon atom. LipY from Mycobacterium tuberculosis discriminated only the unusual diastereoisomeric configuration (Rc, Rp) leading to the most potent inhibitor.


Type : Organophosphate, Cyclic OP, Lipase inhibitor

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Families : Cyclophostin-enolphosphonate ligand of proteins in family
Cutinase Monoglyceridelipase_lysophospholip

References (1)

Title : Enantioselective inhibition of microbial lipolytic enzymes by nonracemic monocyclic enolphosphonate analogues of cyclophostin - Point_2013_J.Med.Chem_56_4393
Author(s) : Point V , Malla RK , Carriere F , Canaan S , Spilling CD , Cavalier JF
Ref : Journal of Medicinal Chemistry , 56 :4393 , 2013
PubMedID: 23651298