Ritter-type reaction of C-(1-bromo-1-deoxy-d-glycopyranosyl)formamides and its application for the synthesis of oligopeptides incorporating anomeric α-amino acids

K. Czifrák, Viktor Gyóllai, K. Kövér, L. Somsák

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

O-Peracetylated or -perbenzoylated C-(1-bromo-1-deoxy-d-glycopyranosyl) formamides of d-gluco, d-galacto, and d-arabino configuration were reacted with Ag(I)-salts or HgO in nitrile solvents to give N-acyl-1-cyano-d- glycopyranosylamines with an axial C-N bond at the anomeric centre. In the presence of HgBr 2, Hg(CN) 2, or InCl 3 the anomer of the above glycosylamine with an equatorial C-N bond was also isolated or detected. In CH 3NO 2 solutions as few as 5-10 equiv of the nitrile were sufficient to get acceptable yields for the products. Under similar conditions N-substituted C-(2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-β-d- galactopyranosyl)formamides gave anomeric spiro-oxazoline derivatives which, upon mild acidic hydrolysis, opened up to di- and tripeptides of anomeric α-amino acids.

Original languageEnglish
Pages (from-to)2104-2112
Number of pages9
JournalCarbohydrate Research
Volume346
Issue number14
DOIs
Publication statusPublished - Oct 18 2011

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Formamides
Oligopeptides
Nitriles
Amino Acids
Dipeptides
Hydrolysis
Salts
Derivatives

Keywords

  • 2-Amino-2-deoxy-hept(hex)-2-ulopyranosononitrile
  • 2-Bromo-2-deoxy-hept(hex)-2-ulopyranosonamide
  • Anomeric α-amino acid
  • Oligopeptide
  • Ritter-reaction

ASJC Scopus subject areas

  • Biochemistry
  • Analytical Chemistry
  • Organic Chemistry

Cite this

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title = "Ritter-type reaction of C-(1-bromo-1-deoxy-d-glycopyranosyl)formamides and its application for the synthesis of oligopeptides incorporating anomeric α-amino acids",
abstract = "O-Peracetylated or -perbenzoylated C-(1-bromo-1-deoxy-d-glycopyranosyl) formamides of d-gluco, d-galacto, and d-arabino configuration were reacted with Ag(I)-salts or HgO in nitrile solvents to give N-acyl-1-cyano-d- glycopyranosylamines with an axial C-N bond at the anomeric centre. In the presence of HgBr 2, Hg(CN) 2, or InCl 3 the anomer of the above glycosylamine with an equatorial C-N bond was also isolated or detected. In CH 3NO 2 solutions as few as 5-10 equiv of the nitrile were sufficient to get acceptable yields for the products. Under similar conditions N-substituted C-(2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-β-d- galactopyranosyl)formamides gave anomeric spiro-oxazoline derivatives which, upon mild acidic hydrolysis, opened up to di- and tripeptides of anomeric α-amino acids.",
keywords = "2-Amino-2-deoxy-hept(hex)-2-ulopyranosononitrile, 2-Bromo-2-deoxy-hept(hex)-2-ulopyranosonamide, Anomeric α-amino acid, Oligopeptide, Ritter-reaction",
author = "K. Czifr{\'a}k and Viktor Gy{\'o}llai and K. K{\"o}v{\'e}r and L. Soms{\'a}k",
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T1 - Ritter-type reaction of C-(1-bromo-1-deoxy-d-glycopyranosyl)formamides and its application for the synthesis of oligopeptides incorporating anomeric α-amino acids

AU - Czifrák, K.

AU - Gyóllai, Viktor

AU - Kövér, K.

AU - Somsák, L.

PY - 2011/10/18

Y1 - 2011/10/18

N2 - O-Peracetylated or -perbenzoylated C-(1-bromo-1-deoxy-d-glycopyranosyl) formamides of d-gluco, d-galacto, and d-arabino configuration were reacted with Ag(I)-salts or HgO in nitrile solvents to give N-acyl-1-cyano-d- glycopyranosylamines with an axial C-N bond at the anomeric centre. In the presence of HgBr 2, Hg(CN) 2, or InCl 3 the anomer of the above glycosylamine with an equatorial C-N bond was also isolated or detected. In CH 3NO 2 solutions as few as 5-10 equiv of the nitrile were sufficient to get acceptable yields for the products. Under similar conditions N-substituted C-(2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-β-d- galactopyranosyl)formamides gave anomeric spiro-oxazoline derivatives which, upon mild acidic hydrolysis, opened up to di- and tripeptides of anomeric α-amino acids.

AB - O-Peracetylated or -perbenzoylated C-(1-bromo-1-deoxy-d-glycopyranosyl) formamides of d-gluco, d-galacto, and d-arabino configuration were reacted with Ag(I)-salts or HgO in nitrile solvents to give N-acyl-1-cyano-d- glycopyranosylamines with an axial C-N bond at the anomeric centre. In the presence of HgBr 2, Hg(CN) 2, or InCl 3 the anomer of the above glycosylamine with an equatorial C-N bond was also isolated or detected. In CH 3NO 2 solutions as few as 5-10 equiv of the nitrile were sufficient to get acceptable yields for the products. Under similar conditions N-substituted C-(2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-β-d- galactopyranosyl)formamides gave anomeric spiro-oxazoline derivatives which, upon mild acidic hydrolysis, opened up to di- and tripeptides of anomeric α-amino acids.

KW - 2-Amino-2-deoxy-hept(hex)-2-ulopyranosononitrile

KW - 2-Bromo-2-deoxy-hept(hex)-2-ulopyranosonamide

KW - Anomeric α-amino acid

KW - Oligopeptide

KW - Ritter-reaction

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