Solid-phase synthesis of conformationally constrained peptidomimetics based on a 3,6-disubstituted-1,4-diazepan-2,5-dione core.
Starting from a Cl-trytyl linked hydroxylamine, a hydroxamic dipeptide having serine in the second position was prepared by using DMTMM as the coupling agent. Mitsunobu cyclization carried out under microwave heating gave very good yields of a 3,6-disubstituted-perhydro-diazepin-2,5-dione. This heterocycle can be used as a new platform for combinatorial chemistry or as a constraint to rigidify a small peptide.
D001381:Azepines / Q000737:chemistry*; D040761:Biomimetic Materials / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006877:Hydroxamic Acids / Q000737:chemistry; D007202:Indicators and Reagents; D008968:Molecular Conformation
D001381:Azepines; D004151:Dipeptides; D006877:Hydroxamic Acids; D007202:Indicators and Reagents