A2 Vertaisarvioitu katsausartikkeli tieteellisessä lehdessä
Hydrolysis and Isomerization of Sugar Phosphates and Carbohydrate Phosphodiesters
Tekijät: Mikkola S
Kustantaja: BENTHAM SCIENCE PUBL LTD
Julkaisuvuosi: 2013
Journal: Current Organic Chemistry
Tietokannassa oleva lehden nimi: CURRENT ORGANIC CHEMISTRY
Lehden akronyymi: CURR ORG CHEM
Numero sarjassa: 14
Vuosikerta: 17
Numero: 14
Aloitussivu: 1525
Lopetussivu: 1544
Sivujen määrä: 20
ISSN: 1385-2728
DOI: https://doi.org/10.2174/1385272811317140008
Tiivistelmä
Phosphoesters are abundant in carbohydrate structures, yet their chemical reactivity is less well known than that of nucleoside phosphoesters. Both classes of compounds contain sugar bound phosphoesters, but structural versatility of carbohydrates means that the reactivity range is wider, and reaction mechanisms not feasible in nucleic acid chemistry, are possible. Sugar phosphates, as well as their phosphodiester and phosphoanhydride derivatives with a phosphate group in glycosylic position, react like acetals under acidic conditions. Substrates with a phosphate group attached to an alcoholic OH react by intramolecular transesterification similar to that of RNA provided that there is a suitably positioned HO-group and a suitable leaving group. If there is a free carbonyl group allowing anomeric equilibria, base-catalyzed phosphate elimination through enediolate intermediates may compete with the cleavage, particularly under alkaline conditions. The few reports on phosphate migration show that the reaction is conceivable, but the competition between cleavage and phosphate migration possibly is different from reactions of nucleic acids and nucleotides.
Phosphoesters are abundant in carbohydrate structures, yet their chemical reactivity is less well known than that of nucleoside phosphoesters. Both classes of compounds contain sugar bound phosphoesters, but structural versatility of carbohydrates means that the reactivity range is wider, and reaction mechanisms not feasible in nucleic acid chemistry, are possible. Sugar phosphates, as well as their phosphodiester and phosphoanhydride derivatives with a phosphate group in glycosylic position, react like acetals under acidic conditions. Substrates with a phosphate group attached to an alcoholic OH react by intramolecular transesterification similar to that of RNA provided that there is a suitably positioned HO-group and a suitable leaving group. If there is a free carbonyl group allowing anomeric equilibria, base-catalyzed phosphate elimination through enediolate intermediates may compete with the cleavage, particularly under alkaline conditions. The few reports on phosphate migration show that the reaction is conceivable, but the competition between cleavage and phosphate migration possibly is different from reactions of nucleic acids and nucleotides.
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