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Emissive Synthetic Cofactors: Enzymatic Interconversions of tz A Analogues of ATP, NAD + , NADH, NADP + , and NADPH
Author(s) -
Hallé François,
Fin Andrea,
Rovira Alexander R.,
Tor Yitzhak
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201711935
Subject(s) - nad+ kinase , cofactor , chemistry , stereochemistry , enzyme , nicotinamide adenine dinucleotide , dehydrogenase , nucleotide , biochemistry , gene
A series of enzymatic transformations, which generate visibly emissive isofunctional cofactors based on an isothiazolo[4,3‐ d ]pyrimidine analogue of adenosine ( tz A ), was developed. Nicotinamide adenylyl transferase condenses nicotinamide mononucleotide and tz ATP to yield N tz AD + , which can be enzymatically phosphorylated by NAD + kinase and ATP or tz ATP to the corresponding N tz ADP + . The latter can be engaged in NADP‐specific coupled enzymatic transformations involving conversion to N tz ADPH by glucose‐6‐phosphate dehydrogenase and reoxidation to N tz ADP + by glutathione reductase. The N tz ADP + / N tz ADPH cycle can be monitored in real time by fluorescence spectroscopy.