Peptide heterocycle conjugates: a diverted edman degradation protocol for the synthesis of N-terminal 2-iminohydantoins.
[reaction: see text] A modified Edman degradation procedure provides an effective means of introducing a heterocycle at the N-terminus of an alpha-amino acid amide or peptide. Reaction of a peptide with an isothiocyanate, followed by dehydrothiolative trapping of the intermediate thiourea, by intramolecular cyclization of the weakly nucleophilic adjacent amide nitrogen, generates an iminohydantoin. A solution-phase parallel synthesis of iminohydantoins and a polymer-supported synthesis of dipeptide- and tripeptide-derived iminohydantoins were also achieved.
Evindar
Ghotas
G
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
Batey
Robert A
RA
D000577:Amides / Q000737:chemistry; D003500:Cyclization; D006827:Hydantoins / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry*; D009842:Oligopeptides / Q000737:chemistry*; D013861:Thiocyanates / Q000737:chemistry; D013890:Thiourea / Q000737:chemistry
D000577:Amides; D006827:Hydantoins; D007097:Imines; D009842:Oligopeptides; D013861:Thiocyanates; D013890:Thiourea