α/β-Chimera peptide synthesis with cyclic β-sugar amino acids: the efficient coupling protocol

Adrienn Nagy, Viktória Goldschmidt Gőz, I. Pintér, Viktor Farkas, A. Perczel

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The synthesis of α/β-chimeras comprises peptide bond formation from α- to β-, from β- to β-, and from β- to α-amino acid residues. The fine-tuned solid phase synthesis of –GXXG– chimera peptides containing the simplest achiral α-amino acid glycine and two cyclic SAAs of different ring size [X denoting cyclic β-Sugar Amino Acids (β-SAA)] is reported, variants containing Fmoc–RibAFU(ip)–OH a furanoid-, and Fmoc–GlcAPU(Me)–OH a pyranoid-type structural “Lego-element”. Systematic search for the best coupling strategy with both H–β-SAA–OHs is described, including the comparison of the different coupling reagents and conditions. Selecting the optimal reagent (from commonly used PyBOP, HATU and HOBt) was assisted by time-resolved 1 H-NMR: formation and stability of the Fmoc protected active esters were compared. We found that PyBOP is the best choice for successfully coupling both H–β-SAA–OH prototypes. The present comparative results open a reasonable route for building efficiently various –β-SAA– containing homo- and heterooligomers.

Original languageEnglish
JournalAmino Acids
DOIs
Publication statusPublished - Jan 1 2019

Fingerprint

Cyclic Amino Acids
Sugar Acids
Sugars
Amino Acids
Peptides
Glycine
Esters
Nuclear magnetic resonance

Keywords

  • Carbopeptoid
  • Foldamers
  • PyBOP
  • Sugar active ester
  • Sugar amino acids

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

α/β-Chimera peptide synthesis with cyclic β-sugar amino acids : the efficient coupling protocol. / Nagy, Adrienn; Goldschmidt Gőz, Viktória; Pintér, I.; Farkas, Viktor; Perczel, A.

In: Amino Acids, 01.01.2019.

Research output: Contribution to journalArticle

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