A multifunctional catalyst that stereoselectively assembles prodrugs
The catalytic stereoselective synthesis of compounds with chiral phosphorus centers remains an unsolved problem. State-of-the-art methods rely on resolution or stoichiometric chiral auxiliaries. Phosphoramidate prodrugs are a critical component of pronucleotide (ProTide) therapies used in the treatm...
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| Published in | Science (American Association for the Advancement of Science) Vol. 356; no. 6336; pp. 426 - 430 |
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| Main Authors | , , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Association for the Advancement of Science
28.04.2017
The American Association for the Advancement of Science |
| Subjects | |
| Online Access | Get full text |
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| Abstract | The catalytic stereoselective synthesis of compounds with chiral phosphorus centers remains an unsolved problem. State-of-the-art methods rely on resolution or stoichiometric chiral auxiliaries. Phosphoramidate prodrugs are a critical component of pronucleotide (ProTide) therapies used in the treatment of viral disease and cancer. Here we describe the development of a catalytic stereoselective method for the installation of phosphorus-stereogenic phosphoramidates to nucleosides through a dynamic stereoselective process. Detailed mechanistic studies and computational modeling led to the rational design of a multifunctional catalyst that enables stereoselectivity as high as 99:1. |
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| AbstractList | The catalytic stereoselective synthesis of compounds with chiral phosphorus centers remains an unsolved problem. State-of-the-art methods rely on resolution or stoichiometric chiral auxiliaries. Phosphoramidate prodrugs are a critical component of pronucleotide (ProTide) therapies used in the treatment of viral disease and cancer. Here we describe the development of a catalytic stereoselective method for the installation of phosphorus-stereogenic phosphoramidates to nucleosides through a dynamic stereoselective process. Detailed mechanistic studies and computational modeling led to the rational design of a multifunctional catalyst that enables stereoselectivity as high as 99:1. Getting phosphorus into healthy shapeProTide therapeutics play a trick on the body, getting nucleoside analogs where they need to be by decorating them with unnatural phosphoramidates in place of ordinary phosphates. These compounds pose an unusual synthetic challenge because their configuration must be controlled at phosphorus; most methods have been refined to manipulate the geometry of carbon. DiRocco et al. report a metal-free, small-molecule catalyst that attains high selectivity for nucleoside phosphoramidation by activating both reaction partners. Kinetic studies with an early prototype revealed a double role for the catalyst that inspired the rational design of a more active and selective dimeric structure.Science, this issue p. 426 The catalytic stereoselective synthesis of compounds with chiral phosphorus centers remains an unsolved problem. State-of-the-art methods rely on resolution or stoichiometric chiral auxiliaries. Phosphoramidate prodrugs are a critical component of pronucleotide (ProTide) therapies used in the treatment of viral disease and cancer. Here we describe the development of a catalytic stereoselective method for the installation of phosphorus-stereogenic phosphoramidates to nucleosides through a dynamic stereoselective process. Detailed mechanistic studies and computational modeling led to the rational design of a multifunctional catalyst that enables stereoselectivity as high as 99:1. ProTide therapeutics play a trick on the body, getting nucleoside analogs where they need to be by decorating them with unnatural phosphoramidates in place of ordinary phosphates. These compounds pose an unusual synthetic challenge because their configuration must be controlled at phosphorus; most methods have been refined to manipulate the geometry of carbon. DiRocco et al. report a metal-free, small-molecule catalyst that attains high selectivity for nucleoside phosphoramidation by activating both reaction partners. Kinetic studies with an early prototype revealed a double role for the catalyst that inspired the rational design of a more active and selective dimeric structure. Science, this issue p. 426 The catalytic stereoselective synthesis of compounds with chiral phosphorus centers remains an unsolved problem. State-of-the-art methods rely on resolution or stoichiometric chiral auxiliaries. Phosphoramidate prodrugs are a critical component of pronucleotide (ProTide) therapies used in the treatment of viral disease and cancer. Here we describe the development of a catalytic stereoselective method for the installation of phosphorus-stereogenic phosphoramidates to nucleosides through a dynamic stereoselective process. Detailed mechanistic studies and computational modeling led to the rational design of a multifunctional catalyst that enables stereoselectivity as high as 99:1. ProTide therapeutics play a trick on the body, getting nucleoside analogs where they need to be by decorating them with unnatural phosphoramidates in place of ordinary phosphates. These compounds pose an unusual synthetic challenge because their configuration must be controlled at phosphorus; most methods have been refined to manipulate the geometry of carbon. DiRocco et al. report a metal-free, small-molecule catalyst that attains high selectivity for nucleoside phosphoramidation by activating both reaction partners. Kinetic studies with an early prototype revealed a double role for the catalyst that inspired the rational design of a more active and selective dimeric structure. Science , this issue p. 426 A doubly activating catalyst efficiently forms key phosphorus-based chiral centers inherent to ProTide therapeutics. The catalytic stereoselective synthesis of compounds with chiral phosphorus centers remains an unsolved problem. State-of-the-art methods rely on resolution or stoichiometric chiral auxiliaries. Phosphoramidate prodrugs are a critical component of pronucleotide (ProTide) therapies used in the treatment of viral disease and cancer. Here we describe the development of a catalytic stereoselective method for the installation of phosphorus-stereogenic phosphoramidates to nucleosides through a dynamic stereoselective process. Detailed mechanistic studies and computational modeling led to the rational design of a multifunctional catalyst that enables stereoselectivity as high as 99:1. |
| Author | Maligres, Peter Limanto, John Dropinski, James Ruck, Rebecca T. Klapars, Artis Reibarkh, Mikhail Campeau, Louis-Charles Hyde, Alan M. Brunskill, Andrew Ji, Yining Sherer, Edward C. DiRocco, Daniel A. Mathew, Rose Davies, Ian W. |
| Author_xml | – sequence: 1 givenname: Daniel A. surname: DiRocco fullname: DiRocco, Daniel A. – sequence: 2 givenname: Yining surname: Ji fullname: Ji, Yining – sequence: 3 givenname: Edward C. surname: Sherer fullname: Sherer, Edward C. – sequence: 4 givenname: Artis surname: Klapars fullname: Klapars, Artis – sequence: 5 givenname: Mikhail surname: Reibarkh fullname: Reibarkh, Mikhail – sequence: 6 givenname: James surname: Dropinski fullname: Dropinski, James – sequence: 7 givenname: Rose surname: Mathew fullname: Mathew, Rose – sequence: 8 givenname: Peter surname: Maligres fullname: Maligres, Peter – sequence: 9 givenname: Alan M. surname: Hyde fullname: Hyde, Alan M. – sequence: 10 givenname: John surname: Limanto fullname: Limanto, John – sequence: 11 givenname: Andrew surname: Brunskill fullname: Brunskill, Andrew – sequence: 12 givenname: Rebecca T. surname: Ruck fullname: Ruck, Rebecca T. – sequence: 13 givenname: Louis-Charles surname: Campeau fullname: Campeau, Louis-Charles – sequence: 14 givenname: Ian W. surname: Davies fullname: Davies, Ian W. |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28450641$$D View this record in MEDLINE/PubMed |
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| Snippet | The catalytic stereoselective synthesis of compounds with chiral phosphorus centers remains an unsolved problem. State-of-the-art methods rely on resolution or... ProTide therapeutics play a trick on the body, getting nucleoside analogs where they need to be by decorating them with unnatural phosphoramidates in place of... Getting phosphorus into healthy shapeProTide therapeutics play a trick on the body, getting nucleoside analogs where they need to be by decorating them with... |
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| SubjectTerms | Amides - chemical synthesis Antineoplastic Agents - chemical synthesis Antiviral Agents - chemical synthesis Cancer Catalysis Catalysts Chemical compounds Chemical synthesis Computer applications Computer Simulation Critical components Drugs Mathematical models Nucleoside analogs Nucleosides Nucleosides - chemical synthesis Phosphates Phosphoric Acids - chemical synthesis Phosphorus Prodrugs Prodrugs - chemical synthesis Selectivity Stereoisomerism Stereoselectivity |
| Title | A multifunctional catalyst that stereoselectively assembles prodrugs |
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