Sustainable synthesis of N-methylated peptides in a continuous-flow fixed bed reactor

Aliz Szloszár, I. Mándity, F. Fülöp

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A rapid, simplified and highly efficient continuous-flow solid-phase peptide synthesis technology is reported for the direct synthesis of mono and multiple N-methylated cyclic alanine and valine peptides. Through an optimization study, we find that only 1.5 equivalents of the amino acids are sufficient for the couplings to maintain excellent conversions. Importantly, the technology is outstandingly sustainable, since three chemical steps are cancelled from the procedure and low amount of solvent is used, compared to traditional technologies. Furthermore, it is also applicable to the coupling of challenging amino acids, since pentavalines were constructed with high yield. The technology was successfully upscaled and peptide cyclization was carried out too. [Figure not available: see fulltext.].

Original languageEnglish
Pages (from-to)21-27
Number of pages7
JournalJournal of Flow Chemistry
Volume8
Issue number1
DOIs
Publication statusPublished - Mar 1 2018

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Peptides
Amino acids
Amino Acids
Cyclization
Valine
Alanine

Keywords

  • continuous-flow
  • N-methylation
  • peptides
  • peptidomimetics
  • SPPS
  • synthesis

ASJC Scopus subject areas

  • Chemistry (miscellaneous)
  • Fluid Flow and Transfer Processes
  • Organic Chemistry

Cite this

Sustainable synthesis of N-methylated peptides in a continuous-flow fixed bed reactor. / Szloszár, Aliz; Mándity, I.; Fülöp, F.

In: Journal of Flow Chemistry, Vol. 8, No. 1, 01.03.2018, p. 21-27.

Research output: Contribution to journalArticle

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