INHIBITION OF Δ8-Δ7-STEROL ISOMERASE AND OF CYCLOEUCALENOL-OBTUSIFOLIOL ISOMERASE BY N-BENZYL-8-AZA-4α,10-DIMETHYL-TRANS-DECAL-3β-OL, AN ANALOGUE OF A CARBOCATIONIC HIGH ENERGY INTERMEDIATE

Article abstract of DOI:10.1016/S0031-9422(00)81106-1

Key Word Index - Rubus fruticosus; Rosaceae; Zea mays; Gramineae; N-benzyl-8-aza-4α,10-dimethyl-trans-decal-3β-ol; high energy intermediate analogues; inhibition of Δ⁸ -> Δ⁷-sterol isomerase and of cycloeucalenol-obtusifoliol isomerase. - An enzymatic assay for the Δ⁸ -> Δ⁷-sterol isomerase, an enzyme involved in sterol biosynthesis, has been developed in higher plants.This assay has been used in the study of various inhibitors.N-Benzyl-8-aza-4α,10-dimethyl-trans-decal-3β-ol was designed to mimic the C-8 and C-9 carbocationic high energyintermediates occuring during the reactions catalysed by the Δ⁸ -> Δ⁷-sterol isomerase and the cycloeucalenol obtusifoliol isomerase, respectively.In accordance with the 'transition state analogues' theory, this analogue of a high energy intermediate was found to be a very potent and specific inhibitor of the two enzymatic reactions both in vitro and in vivo.