138458-26-1Relevant academic research and scientific papers
New synthesis of sn-1,2- and sn-2,3-O-diacylglycerols application to the synthesis of enantiopure phosphonates analogous to triglycerides: A new class of inhibitors of lipases
Marguet, Frank,Cavalier, Jean-Francois,Verger, Robert,Buono, Gerard
, p. 1671 - 1678 (1999)
Phosphonate compounds mimic the first transition state occurring during enzymatic carboxyester hydrolysis of natural substrates by forming a covalent bond with the catalytic serine. However, until now the organophosphorus compounds used in the inhibition studies more or less resembled a natural triglyceride substrate. In order to elucidate the interfacial activation and the mechanism of action of lipases, specific inhibitors need to be prepared. To achieve this goal, enantiomerically pure sn-1,2- and sn-2,3O- didecanoylglycerol compounds were prepared - starting from a C-4 chiral synthon, 3-buten-1,2-diol - and treated with n-pentylphosphonic dichloride and p-nitrophenol to afford the corresponding diastereomeric phosphonates, which were acylglycerol analogs. Subsequent separation of each of the phosphonate diastereomers A/B or ent-A/ent-B, performed by HPLC, led to four enantiopure stereoisomers that will be investigated as inhibitors of Human Pancreatic Lipase (HPL) and Human Gastric Lipase (HGL) using the monomolecular film technique.
Amine assisted enzymatic esterification of 1,2-diol monotosylates
Boaz,Zimmerman
, p. 153 - 156 (2007/10/02)
The enzymatic esterification of 1,2-diol monotosylates in organic solvent under standard conditions often fails to achieve the desired 50% conversion due to enzyme inactivation by acidic contaminants. The inclusion of an amine affords rapid conversion to
