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

Govindan Chettur, Stephen J. Benkovic

Research output: Contribution to journalArticle

39 Citations (Scopus)

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

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Phosphoribosylglycinamide Formyltransferase
Phosphates
Phosphorylation
Anhydrides
Glycine
Condensation
acetamide
propylene
4-toluenesulfonic acid

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

Chettur, Govindan ; Benkovic, Stephen J. / A new chemical synthesis of 2-amino-(N-d-ribofuranosyl)acetamide 5′-phosphate. In: Carbohydrate Research. 1977 ; Vol. 56, No. 1. pp. 75-86.
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A new chemical synthesis of 2-amino-(N-d-ribofuranosyl)acetamide 5′-phosphate. / Chettur, Govindan; Benkovic, Stephen J.

In: Carbohydrate Research, Vol. 56, No. 1, 06.1977, p. 75-86.

Research output: Contribution to journalArticle

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AB - 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.

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