Some non-anomerically C-C-linked carbohydrate amino acids related to leucine-synthesis and structure determination

Carbohydr Res. 2003 Jun 23;338(13):1349-57. doi: 10.1016/s0008-6215(03)00176-9.

Abstract

(5'R)-5'-Isobutyl-5'-[methyl (4R)-2,3-O-isopropylidene-beta-L-erythrofuranosid-4-C-yl]-imidazolidin-2',4'-dione was synthesised starting from methyl 2,3-O-isopropylidene-alpha-D-lyxo-pentodialdo-1,4-furanoside via methyl 6-deoxy-6-isopropyl-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose applying the Bucherer-Bergs reaction. Its 5'-R configuration was confirmed by X-ray crystallography. Corresponding alpha-amino acid-methyl (5R)-5-amino-5-C-carboxy-5,6-dideoxy-6-isopropyl-alpha-D-lyxo-hexofuranoside (alternative name: 2-[methyl (4R)-beta-L-erythrofuranosid-4-C-yl]-D-leucine) was obtained from the above hydantoin by acid hydrolysis of the isopropylidene group followed by basic hydrolysis of the hydantoin ring. Analogous derivatives with 5S configuration, formed in a minority, were also isolated and characterised.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Sugars / chemical synthesis*
  • Amino Sugars / chemistry
  • Carbohydrate Conformation
  • Crystallography, X-Ray
  • Hydantoins / chemistry
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Leucine / analogs & derivatives*
  • Leucine / chemical synthesis
  • Leucine / chemistry
  • Magnetic Resonance Spectroscopy
  • Monosaccharides / chemical synthesis*
  • Monosaccharides / chemistry
  • Stereoisomerism

Substances

  • (5'R)-5'-isobutyl-5'-(methyl (4R)-2,3-O-isopropylidene-beta-L-erythrofuranosid-4-C-yl)-imidazolidin-2',4'-dione
  • Amino Sugars
  • Hydantoins
  • Imidazoles
  • Monosaccharides
  • Leucine