title: Efficient synthesis of peptides by extension at the N- and C-terminii of arginine.
abstract: L-N(omega)-nitroarginine and L-arginine were coupled with N-(Cbz-alpha-aminoacyl)benzotriazoles and N-Cbz-dipeptidoylbenzotriazoles to provide arginine LL-dipeptides 9a-e, 11a-d; LLL-tripeptides 18a-c, 20; and diastereomeric mixtures (9b+9b'), (9c+9c'), (11b+11b') and (18c+18c') [compound numbers written within parentheses represent a diastereomeric mixture or racemate; compound numbers without parentheses represent an achiral compound or a single enantiomer] by extension at the N-terminus of arginine, in isolated yields of 66-95% with complete retention of chirality as evidenced by NMR and HPLC analysis. Arginine LL-dipeptides 15a-d were synthesized by extension at the C-terminus of arginine in isolated yield of 66-80%, using benzotriazole activated arginine L-(omega)NO2-Arg-Bt, 13. Our methodology has also been used to synthesize the protected RGD peptide (Cbz(alpha)-L-(omega)NO2-Arg-Gly-L-Asp-(OH)2) 21.
authors.affiliation: Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu
authors.forename: Alan R
authors.initials: AR
authors.lastname: Katritzky
authors.forename: Geeta
authors.initials: G
authors.lastname: Meher
authors.forename: Tamari
authors.initials: T
authors.lastname: Narindoshvili
mesh_terms: D001120:Arginine / Q000031:analogs & derivatives / Q000737:chemistry*; D008968:Molecular Conformation; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D009842:Oligopeptides; D001120:Arginine