Dimethylformamide → Benzyloxycarbonyl-L-phenylalanine

Participants

Reaction Steps

A solution of N-CBZ-phenylalanine oximinobiotin methyl ester (10.0 mg, 0.018 mmol) in distilled H2O (0.99 mL)/DMF (0.01 mL) was treated with lipase (candida cylindracea, 3 mg, ca. 2000 units) and analyzed by HPLC. After 1 H, the probiotin was cleaved to form N-CBZ-phenylalanine and oximinobiotin methyl ester. Control samples containing no lipase did not show evidence of cleavage. The crude reaction mixture caused a displacement of HABA from the HABA/avidin or HABA/streptavidin complexes, confirming that the oximinobiotin methyl ester was produced by the hydrolysis. Control reactions which did not contain lipase failed to displace the HABA from the HABA/avidin or HABA/streptavidin complexes. This shows that probiotin did not bind to avidin or streptavidin until activated, that is until it was converted to oximinobiotin methyl ester, by lipase.

Provenance & Evidence