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Competitive inhibitors of yeast phosphoglucose isomerase: synthesis and evaluation of new types of phosphorylated sugars from the synthond-arabinonolactone-5-phosphate

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
318
Identifiers
DOI: 10.1016/s0008-6215(99)00100-7
Keywords
  • Enzyme Inhibitors
  • Hydroxamic Acids
  • Phosphoglucose Isomerase
  • Sugar Phosphates
Disciplines
  • Medicine

Abstract

Abstract Designed as competitive inhibitors of the isomerization reaction catalyzed by the potential chemotherapeutic target phosphoglucose isomerases (PGI), d-arabinonamide-5-phosphate and d-arabinonhydrazide-5-phosphate were synthesized and fully characterized. These new types of phosphorylated sugar derivatives were easily and efficiently obtained in a one-step procedure from the promising synthon d-arabinono-1,4-lactone 5-phosphate. These two compounds proved to be new good competitive inhibitors of yeast PGI with the substrate d-fructose-6-phosphate, though not as strong as d-arabinonhydroxamic acid-5-phosphate. Overall, our results are in accord with the postulated 1,2- cis-enediolate species as a probable high-energy intermediate of the PGI-catalyzed reaction.

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