Organophosphorus Analogues and Derivatives of the Natural l -Amino Carboxylic Acids and Peptides. I. Enzymatic Synthesis of d -, Dl -, and l -Phosphinothricin and Their Cyclic Analogues

Acetylation of d-, Dl-, and l-3-amino-2-pyrrolidinone (1) to the 3-acetamido derivative 2 and treatment with ethyl methylphosphinate afforded the addition product 3. Strict selectivity was observed in the enzyme-catalyzed hydrolysis with the enzyme phosphodiesterase I, acylase, glutaminase, and α-chymotrypsin. The ester 7 and 1,2-azaphospholidine (8) were isolated by esterification of l-phosphinothricin (6).