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Asymmetric phosphorylation through catalytic P(III) phosphoramidite transfer: enantioselective synthesis of D-myo-inositol-6-phosphate. | LitMetric

AI Article Synopsis

  • Despite the widespread use of phosphoramidite chemistry for creating biophosphates, using it in asymmetric phosphoramidite transfer for phosphate esters has been mostly untested.
  • Researchers found that a tetrazole-functionalized peptide paired with 10-Å molecular sieves acts as an enantioselective catalyst for transferring phosphites effectively.
  • This method has led to a streamlined process for synthesizing myo-inositol-6-phosphate and provides new insights into using phosphate as a directing group for selectively resolving protected inositol monophosphate.

Article Abstract

Despite the ubiquitous use of phosphoramidite chemistry in the synthesis of biophosphates, catalytic asymmetric phosphoramidite transfer remains largely unexplored for phosphate ester synthesis. We have discovered that a tetrazole-functionalized peptide, in the presence of 10-Å molecular sieves, functions as an enantioselective catalyst for phosphite transfer. This chemistry in turn has been used as the key step in a streamlined synthesis of myo-inositol-6-phosphate. Mechanistic insights implicate phosphate as a directing group for a highly selective kinetic resolution of a protected inositol monophosphate. This work represents a distinct and efficient method for the selective catalytic phosphorylation of natural products.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2996443PMC
http://dx.doi.org/10.1073/pnas.1001111107DOI Listing

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