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[Derivatives of N-amidinoproline and their use in conventional and solid phase peptide synthesis].

Authors
  • Burov, S V
  • Moskalenko, Iu E
  • Leko, M V
  • Dorosh, M Iu
  • Panarin, E F
Type
Published Article
Journal
Bioorganicheskaia khimiia
Publication Date
Jan 01, 2006
Volume
32
Issue
6
Pages
565–573
Identifiers
PMID: 17180906
Source
Medline
License
Unknown

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.

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