Cryochemistry

Freezing effect on peptide coupling in different organic solutions

Tamás Vajda, Gyula Szókán, M. Hollósi

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The freezing effect on peptide coupling in organic solutions of different polarity has been investigated and compared with the results obtained in liquid phase. The model reaction of DCC-activated coupling of Boc-Ala-Phe-OH with H-Ala-OBut has been carried out in dioxane, dimethylsulfoxide and formamide, as well as in mixtures (90%/10%, v/v) of dioxane with acetonitrile, dimethylformamide, dimethylsulfoxide and formamide. The reactions have been traced and evaluated by RP-HPLC analysis. Freezing the reaction mixture resulted in all cases in a significant suppression of the N-dipeptidylurea side-product formation together with a slight decrease of tripeptide epimerization. The coupling yields and the side effects depended on the solvent, with the dioxane and dioxane/acetonitrile mixture produced the best results. The role of freezing and solvent in the improved results is discussed.

Original languageEnglish
Pages (from-to)300-304
Number of pages5
JournalJournal of Peptide Science
Volume4
Issue number4
Publication statusPublished - Jun 1998

Fingerprint

Freezing
Peptides
Dimethyl Sulfoxide
Dimethylformamide
High Pressure Liquid Chromatography
1,4-dioxane
Liquids
acetonitrile
formamide

Keywords

  • Cryochemistry
  • Frozen organic solution
  • Peptide coupling

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Analytical Chemistry

Cite this

Cryochemistry : Freezing effect on peptide coupling in different organic solutions. / Vajda, Tamás; Szókán, Gyula; Hollósi, M.

In: Journal of Peptide Science, Vol. 4, No. 4, 06.1998, p. 300-304.

Research output: Contribution to journalArticle

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