Synthesis and microbial transformation of β-amino nitriles

Abstract

Rhodococcus equi A4, Rhodococcus erythropolis NCIMB 11540 and Rhodococcus sp. R312 were investigated towards their ability to produce β-amino amides and acids from β-amino nitriles. The microorganisms show comparable trends: five-membered alicyclic 2-amino nitriles were transformed significantly faster than the six-membered compounds and the products of trans-2-amino nitriles (amides and acids) were formed considerably faster than the cis-counterparts (amides). The trans-five membered nitriles gave the amides ( 1b , 5b ) in excellent enantiomeric excess (94–99%), the biotransformation of trans-six membered substrates resulted in the formation of the acid ( 3c , 7c ) in excellent ee (87–99%). The ee's of the cis-compounds were throughout lower. Fifteen new substances were synthesized and characterized in the course of this work.