title: [Derivatives of N-amidinoproline and their use in conventional and solid phase peptide synthesis].
abstract: N-Amidinoproline, a hybrid structure modeling key features of the Arg-Pro sequence, was synthesized. The activation of carboxyl group of free N-amidinoproline was found to result in the formation of a cyclic side product, whose structure was confirmed by ESI MS, 1H NMR, and 13C NMR spectra. The preparation of N-(mesitylenesulfonylamidino)-L-proline using the mesitylenesulfonyl derivative of 2-methylisourea was demonstrated to be accompanied by partial racemization. The target product was synthesized by modification of N-amidinoproline by mesitylenesulfonyl chloride. The possibility of using N-amidinoproline in the N-terminal modification of a peptide chain was shown by the example of synthesis of an analogue of the 95-98 fragment of fibrinogen alpha chain.
authors.forename: S V
authors.initials: SV
authors.lastname: Burov
authors.forename: Iu E
authors.initials: IuE
authors.lastname: Moskalenko
authors.forename: M V
authors.initials: MV
authors.lastname: Leko
authors.forename: M Iu
authors.initials: MIu
authors.lastname: Dorosh
authors.forename: E F
authors.initials: EF
authors.lastname: Panarin
mesh_terms: D004151:Dipeptides / Q000138:chemical synthesis / Q000737:chemistry; D005340:Fibrinogen / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular / Q000379:methods; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D017433:Protein Structure, Secondary; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods
chemical_list: D004151:Dipeptides; D010455:Peptides; C039357:arginylproline; D005340:Fibrinogen; D011392:Proline