10075-38-4Relevant articles and documents
Synthesis and evaluation of chlorinated substrate analogues for farnesyl diphosphate synthase
Heaps, Nicole A.,Poulter, C. Dale
experimental part, p. 1838 - 1843 (2011/06/22)
Substrate analogues for isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), where the C3 methyl groups were replaced by chlorine, were synthesized and evaluated as substrates for avian farnesyl diphosphate synthase (FPPase). The IPP analogue (3-ClIPP) was a cosubstrate when incubated with dimethylallyl diphosphate (DMAPP) or geranyl diphosphate (GPP) to give the corresponding chlorinated analogues of geranyl diphosphate (3-ClGPP) and farnesyl diphosphate (3-ClFPP), respectively. No products were detected in incubations of 3-ClIPP with 3-ClDMAPP. Incubation of IPP with 3-ClDMAPP gave 11-ClFPP as the sole product. Values of KM 3-ClIPP (with DMAPP) and KM 3-ClDMAPP (with IPP) were similar to those for IPP and DMAPP; however, values of κcat for both analogues were substantially lower. These results are consistent with a dissociative electrophilic alkylation mechanism where the rate-limiting step changes from heterolytic cleavage of the carbon-oxygen bond in the allylic substrate to alkylation of the double bond of the homoallylic substrate. 2011 American Chemical Society.
11-Substituted-desA-pregnanes and derivatives thereof
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, (2008/06/13)
This invention is directed to 11-substituted-desA-pregnanes and derivatives thereof which are useful as intermediates in the production of 9β,10α-known steroids of the pregnane series. These latter compounds can be utilized as progestational and salt-retaining agents.