Synthetic routes to N-(1-deoxy-d-fructos-1-yl)amino acids by way of reductive amination of hexos-2-uloses

Donald J. Walton, John Douglas Mcpherson, Torsten Hvidt, Walter A. Szarek

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

There are described two routes to the synthesis of N-(1-deoxyd-fructos-1-yl) derivatives of l-valine, l-leucine, l-methionine, l-phenylalanine, and 6-aminohexanoic acid. One route involved reductive amination of d-arabino-hexos-2-ulose in the presence of sodium cyanoborohydride; yields were limited by the formation of significant quantities of N-(1-deoxyhexitol-1-yl)amino acids, which were difficult to remove. this drawback was overcome in the second route, which involved reductive amination of 2,3:4,5-di-O-isopropylidene-aldehydo-β-d-arabino-hexos-2-ulo-2,6-pyranose; following a deblocking step, N-(1-deoxy-d-fructos-1-yl) derivatives of the aforementioned amino acids were obtained in yields which were at least double those reported for the current procedure involving the reaction of an amino acid with d-glucose, and an Amadori type of rearrangement of the resulting d-glucosylamine.

Original languageEnglish (US)
Pages (from-to)123-130
Number of pages8
JournalCarbohydrate Research
Volume167
Issue numberC
DOIs
StatePublished - Sep 15 1987
Externally publishedYes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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