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Synthesis and characterization of 16β-azidopregn-5-en-3β,17α-diol-21-one are reported. The azido steroid was studied by docking simulations as a substrate for a range of steroid-converting enzymes, including bacterial cholesterol oxidase and mammalian cytochromes P450 17-hydroxylase/17,20-lyase (CYP17A1) and 21-hydroxylase (CYP21A2). The derivative was calculated to localize similarly to natural substrates with binding energy values ranging from -7.2 to -11.9 kcal·mol-1. A fluorescent triazole derivative of 16βazidopregn-5-en-3β,17α-diol-21-one has been obtained using click chemistry approach. The azido steroid is proposed as a suitable molecular tool for studies of steroid biotransformations.

Synthesis and in silico evaluation of 16?-azido pregnenolone analogue as a clickable substrate for steroid-converting enzymes