Application of gel-phase 13c-nmr to monitor solid phase peptide synthesis

E. Giralt, Jose Rizo-Rey, E. Pedroso

Research output: Contribution to journalArticle

93 Scopus citations

Abstract

The results presented in this article show the general applicability of gel-phase 13C-NMR to monitor solid phase peptide synthesis on the most commonly used polystyrene-based resins. The optimal conditions to acquire gel-phase 13C-NMR spectra of copoly(styrene-l%-divinylbenzene) has been determined. The technique proved to be applicable to characterize polystyrene-based starting supports as well as to the determination of their degree of functionality and purity. The stage-by-stage 13C-NMR characterization of the growing peptide chain during the synthesis of tripeptide H-Asn-(N-Me)Ala-Thr-NH2 on a benzhydrylamine resin is described. The structural information, derived from this technique is relevant for the synthetic process as the spectra can be acquired under similar conditions. The characteristics of the spectra facilitate monitoring of coupling and deprotection reactions.

Original languageEnglish (US)
Pages (from-to)4141-4152
Number of pages12
JournalTetrahedron
Volume40
Issue number20
DOIs
StatePublished - 1984

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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