Characterization of Phosphoranes Obtained by the Spontaneous Carbonyl-Catalyzed Phosphorylation of Monosaccharides and Polyols in Aqueous Media.
activation
biophosphorylation
monosaccharides
phosphoranes
polyols
Journal
Chembiochem : a European journal of chemical biology
ISSN: 1439-7633
Titre abrégé: Chembiochem
Pays: Germany
ID NLM: 100937360
Informations de publication
Date de publication:
17 02 2020
17 02 2020
Historique:
received:
15
05
2019
revised:
14
07
2019
pubmed:
17
8
2019
medline:
5
2
2021
entrez:
17
8
2019
Statut:
ppublish
Résumé
Phosphorylation is a very important biochemical process in metabolism and biochemical marking. The mechanism for the biophosphorylation of substrates and the hydrolysis/transesterification of RNA has been suggested to proceed through phosphorane intermediates. Although the phosphorane intermediate/transition state has long been a subject of many theoretical models and studies, it has neither been isolated nor characterized, with most information derived from the hydrolysis and radiolabeling of cyclic phosphotriesters. We herein present the first report of the spontaneous phosphorylation of sugars and polyols in the absence of enzymes. That is, aldehydes and ketones combine with inorganic phosphates to form activated phosphates that phosphorylate alcohols without the requirement of any enzyme or additional activating agent. This phosphorylation is particularly favored in polyhydroxycarbonyls that can form internal cyclic acetals to give rise to the corresponding acetal phosphoranes. We have further characterized these phosphoranes and demonstrated their dehydration to the corresponding phosphates by using high-resolution mass spectroscopy. The phosphorylation of adenosine and uridine to form the corresponding phosphoranes was also achieved.
Identifiants
pubmed: 31418517
doi: 10.1002/cbic.201900328
doi:
Substances chimiques
Monosaccharides
0
Phosphates
0
Phosphoranes
0
Polymers
0
polyol
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
473-476Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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