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Proceedings of the National Academy of Sciences of the United States of America logoLink to Proceedings of the National Academy of Sciences of the United States of America
. 1988 Oct;85(19):7174–7176. doi: 10.1073/pnas.85.19.7174

Nonenzymatic synthesis of 5-aminoimidazole ribonucleoside and recognition of its facile rearrangement.

M P Groziak 1, B Bhat 1, N J Leonard 1
PMCID: PMC282146  PMID: 3174626

Abstract

5-Amino-1-beta-D-ribofuranosylimidazole 5'-monophosphate (AIR, 1) is the ubiquitous precursor to the purine ribonucleotides in vivo, and it serves as the biochemical precursor to the pyrimidine portion of thiamin (vitamin B1) in certain prokaryotic organisms. The corresponding ribonucleoside (AIRs, 5b) was prepared via chemical (nonenzymatic) synthesis from 5-amino-1-beta-D-ribofuranosylimidazole-4-carboxamide. The tri-O-acetylated derivative of AIRs (5a) was also prepared, and it was shown to undergo a facile ring transformation in aqueous pH 7 buffer to afford N-(imidazol-4-yl)-2,3,5-tri-O-acetyl-D-ribofuranosylamine as a 1:2 mixture of alpha and beta anomers (6a). Under similar conditions, compound 5b affords the corresponding unprotected beta-ribonucleosides 6b. This Dimroth-type ring transformation reaction of 5 to 6, which occurs primarily in neutral aqueous solution, may be responsible for the previously reported lability of AIRs and its derivatives. It may also have relevance to the postulated early biotic pathway to the 9- and 3-substituted purine nucleotide components of an all-purine biopolymer.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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