A new chemical synthesis of 2-amino-(N-d-ribofuranosyl)acetamide 5′-phosphate

Govindan Chettur, Stephen J. Benkovic

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39 Scopus citations

Abstract

2-amino-(N-d-ribosyl)acetamide 5′-phosphate (GAR, 10) has been prepared in a readily scaled-up synthesis from 2,3-O-isopropylidene-d-ribofuranosylamine p-toluenesulfonate (3) by condensation with the mixed anhydride of N-(benzyloxy-carbonyl)glycine, followed by phosphorylation with 2-cyanoethyl phosphate and removal of the protecting groups. By varying the conditions, the α-4 and the β-5 anomers could be obtained and separated from each other. Anomerization occurs upon removing the O-isopropylidene group from either 7 or 8, so that the final compound (10) is an equimolar mixture of both anomers, of which only one is active toward GAR-transformylase.

Original languageEnglish (US)
Pages (from-to)75-86
Number of pages12
JournalCarbohydrate Research
Volume56
Issue number1
DOIs
StatePublished - Jun 1977

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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