Synthesis of asymmetrized 2-benzyl-1,3-diaminopropane by a chemoenzymatic route: a tool for combinatorially developing peptidomimetics

Both enantiomers of monoacetamide 5, together with 'dipeptides' 30a,b and m onocarbamates 24, (R)-43 and (S)-43, all derived from 2-benzyl-1,3-diaminop ropane 4, were synthesized by a chemoenzymatic route starting from the know n monoacetate 12. The behaviour of 4 and of the bis(acylated) derivatives 8 -11 with respect to hydrolytic enzymes is also presented, together with an extensive study on the configurational stability of monoacylated derivative s of 4. (C) 1999 Elsevier Science Ltd. All rights reserved.