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1.3.3.4.2 Acid Phosphatases and Transphosphorylation Mechanism

DOI: 10.1055/sos-SD-214-00162

Wever, R.; Babich, L.; Hartog, A. F.Science of Synthesis: Biocatalysis in Organic Synthesis, (20151233.

Axelrod[‌60‌] and Appleyard[‌61‌] were the first to demonstrate transphosphorylation by non-ATP dependent enzymes. They showed that acid phosphatases (EC 3.1.3.2) from orange juice and prostatic extracts, respectively, catalyzed the transfer of the phosphate group from a phosphorylated donor to an acceptor. Transphosphorylation reactions with pyrophosphate (PPi), d-glucose 6-phosphate, and nucleoside 5′-triphosphate as phosphate donor are also catalyzed by the membrane-bound mammalian glucose 6-phosphatase from kidney and liver.[‌62‌] Interestingly, this enzyme has the same active site as many bacterial acid phosphatases.[‌63‌] Many bacterial species, e.g. E. coli,[‌64‌,‌65‌] Salmonella typhimurium,[‌66‌] and Citrobacter,[‌67‌] express phosphatases with phosphotransferase activity. These enzymes show broad substrate specificity, e.g. the 3′-hydroxy of the ribose in nicotinamide riboside, the hydroxy moiety of adenosine in nicotinamide adenine dinucleotide (NAD),[‌65‌] and simple alcohols and polyalcohols are phosphorylated by suitable donors. Synthetic procedures became possible when Asanoʼs group showed in pioneering studies that nonspecific acid phosphatases effectively transfer a phosphate group from pyrophosphate to nucleosides (Scheme 7).[‌15‌]

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