Synthesis of 2-(4,6-Dimethoxy-1,3,5-triazin-2-yloxyimino) derivatives: Application in solution peptide synthesis

Tarfah I. Al-Warhi, Hassan M.A. AL-Hazimi, Ayman El-Faham, Fernando Albericio

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A new class of 1,3,5-triazinyloxyimino derivatives were prepared, characterized and tested for reactivity in solution peptide synthesis. The new triazinyloxyimino derivatives failed to activate the carboxyl group during formation of peptide bonds, but gave the corresponding N-triazinyl amino acid derivatives as a major product. The oxyma (ethyl 2-cyano-2-(hydroxyimino) acetate) uronium salt was superior to other uronium salts in terms of racemization, while 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT, 9) gave the best results.

Original languageEnglish
Pages (from-to)9403-9417
Number of pages15
JournalMolecules
Volume15
Issue number12
DOIs
Publication statusPublished - 1 Dec 2010

Fingerprint

peptides
Salts
salts
Derivatives
Triazines
Peptides
carboxyl group
synthesis
amino acids
acetates
reactivity
Amino Acids
products
D-4-chloro-17 beta-hydroxy-3-oxo-17 alpha-methylandrosta-1,4-diene
oxyma
ethyl 2-cyano-2-(hydroxyimino)acetate

Keywords

  • Coupling reagents
  • Racemization
  • Solution phase peptide synthesis
  • Triazinyloximino derivatives
  • Uronium salt

Cite this

Al-Warhi, Tarfah I. ; AL-Hazimi, Hassan M.A. ; El-Faham, Ayman ; Albericio, Fernando. / Synthesis of 2-(4,6-Dimethoxy-1,3,5-triazin-2-yloxyimino) derivatives : Application in solution peptide synthesis. In: Molecules. 2010 ; Vol. 15, No. 12. pp. 9403-9417.
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Synthesis of 2-(4,6-Dimethoxy-1,3,5-triazin-2-yloxyimino) derivatives : Application in solution peptide synthesis. / Al-Warhi, Tarfah I.; AL-Hazimi, Hassan M.A.; El-Faham, Ayman; Albericio, Fernando.

In: Molecules, Vol. 15, No. 12, 01.12.2010, p. 9403-9417.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of 2-(4,6-Dimethoxy-1,3,5-triazin-2-yloxyimino) derivatives

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