Automated solid-phase synthesis of glycopeptides. Incorporation of unprotected mono- and disaccharide units of n-glycoprotein antennae into T cell epitopic peptides

Laszlo Otvos, Laszlo Urge, M. Hollósi, Krzysztof Wroblewski, Grazyna Graczyk, Gerald D. Fasman, Jan Thurin

Research output: Contribution to journalArticle

60 Citations (Scopus)

Abstract

A new reagent for custom synthesis of N-glycosylated peptides, Fmoc-Asn[GlcNAc(1»4)-GlcNAc]-OH, has been prepared. The O-glycosidic bond survived the trifluoroacetic acid cleavage. High coupling efficiencies were obtained when this glycoamino acid derivative was used for solid-phase synthesis of a test peptide and a T cell epitopic dodecapeptide containing an Asn residue in mid-chain position. An automated peptide synthesizer was used to produce the parent Asn peptide and its N-acetyl-glycosyl mono- and disaccharide derivatives.

Original languageEnglish
Pages (from-to)5889-5892
Number of pages4
JournalTetrahedron Letters
Volume31
Issue number41
DOIs
Publication statusPublished - 1990

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Solid-Phase Synthesis Techniques
T-cells
Glycopeptides
Monosaccharides
Disaccharides
Glycoproteins
Antennas
T-Lymphocytes
Peptides
Peptide T
Trifluoroacetic Acid
Derivatives
Acids
difluprednate

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Automated solid-phase synthesis of glycopeptides. Incorporation of unprotected mono- and disaccharide units of n-glycoprotein antennae into T cell epitopic peptides. / Otvos, Laszlo; Urge, Laszlo; Hollósi, M.; Wroblewski, Krzysztof; Graczyk, Grazyna; Fasman, Gerald D.; Thurin, Jan.

In: Tetrahedron Letters, Vol. 31, No. 41, 1990, p. 5889-5892.

Research output: Contribution to journalArticle

Otvos, Laszlo ; Urge, Laszlo ; Hollósi, M. ; Wroblewski, Krzysztof ; Graczyk, Grazyna ; Fasman, Gerald D. ; Thurin, Jan. / Automated solid-phase synthesis of glycopeptides. Incorporation of unprotected mono- and disaccharide units of n-glycoprotein antennae into T cell epitopic peptides. In: Tetrahedron Letters. 1990 ; Vol. 31, No. 41. pp. 5889-5892.
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