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- W2749616727 abstract "Pterin-containing natural products have diverse functions in life, but an efficient and easy scheme for their in vitro synthesis is not available. Here we report a chemoenzymatic 14-step, one-pot synthesis that can be used to generate 13C- and 15N-labeled dihydrofolates (H2F) from glucose, guanine, and p-aminobenzoyl-l-glutamic acid. This synthesis stands out from previous approaches to produce H2F in that the average yield of each step is >91% and it requires only a single purification step. The use of a one-pot reaction allowed us to overcome potential problems with individual steps during the synthesis. The availability of labeled dihydrofolates allowed the measurement of heavy-atom isotope effects for the reaction catalyzed by the drug target dihydrofolate reductase and established that protonation at N5 of H2F and hydride transfer to C6 occur in a stepwise mechanism. This chemoenzymatic pterin synthesis can be applied to the efficient production of other folates and a range of other natural compounds with applications in nutritional, medical, and cell-biological research." @default.
- W2749616727 created "2017-08-31" @default.
- W2749616727 creator A5002119734 @default.
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- W2749616727 creator A5011146439 @default.
- W2749616727 creator A5044842810 @default.
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- W2749616727 date "2017-09-06" @default.
- W2749616727 modified "2023-10-16" @default.
- W2749616727 title "Chemoenzymatic Assembly of Isotopically Labeled Folates" @default.
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- W2749616727 doi "https://doi.org/10.1021/jacs.7b06358" @default.
- W2749616727 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/28820585" @default.
- W2749616727 hasPublicationYear "2017" @default.
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