Synthesis of Selectively Labeled D-Fructose and D-Fructose Phosphate Analogs Locked in the Cyclic Furanose Form

Rachel Persky, Amnon Albeck

Research output: Contribution to journalArticlepeer-review

Abstract

2,5-Anhydroglucitol and 2,5-anhydromannitol and their 6-phosphate and 1,6-diphosphate derivatives are cyclic analogues of the α and β anomers of d-fructofuranose, d-fructofuranose-6-phosphate, and d-fructofuranose-1,6-diphosphate. They were synthesized from protected d-mannose or d-glucose. The synthetic method was developed with emphasis on selective 2H labeling of these compounds, as a model for 3H incorporation, which will be used for further biochemical studies. A key cyclization step, based on a benzyl ether nucleophilic attack on an activated alcohol, constructed the ring system. The stereochemistry at C2 (α/β anomers) and at C5 (D sugar) was controlled by selective epimerizations. Mono- and diphosphate analogues were obtained from the same intermediate by changing the sequence of deprotection and phosphorylation steps.
Original languageAmerican English
Pages (from-to)5632-5638
JournalThe Journal of Organic Chemistry
Volume65
Issue number18
StatePublished - 2000

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