[Derivatives of N-amidinoproline and their use in conventional and solid phase peptide synthesis].
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.
Burov
S V
SV
Moskalenko
Iu E
IuE
Leko
M V
MV
Dorosh
M Iu
MIu
Panarin
E F
EF
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
D004151:Dipeptides; D010455:Peptides; C039357:arginylproline; D005340:Fibrinogen; D011392:Proline