Chemoselective multicomponent one-pot assembly of purine precursors in water. Powner, M. W., Sutherland, J. D., & Szostak, J. W. Journal of the American Chemical Society, 132(46):16677–16688, 2010. doi abstract bibtex The recent development of a sequential, high-yielding route to activated pyrimidine nucleotides, under conditions thought to be prebiotic, is an encouraging step toward the greater goal of a plausible prebiotic pathway to RNA and the potential for an RNA world. However, this synthesis has led to a disparity in the methodology available for stepwise construction of the canonical pyrimidine and purine nucleotides. To address this problem, and further explore prebiotically accessible chemical systems, we have developed a high-yielding, aqueous, one-pot, multicomponent reaction that tethers masked-sugar moieties to prebiotically plausible purine precursors. A pH-dependent three-component reaction system has been discovered that utilizes key nucleotide synthons 2-aminooxazole and 5-aminoimidazoles, which allows the first divergent purine/pyrimidine synthesis to be proposed. Due to regiospecific aminoimidazole tethering, the pathway allows N9 purination only, thus suggesting the first prebiotically plausible mechanism for regiospecific N9 purination. © 2010 American Chemical Society.
@article{Powner2011b,
abstract = {The recent development of a sequential, high-yielding route to activated pyrimidine nucleotides, under conditions thought to be prebiotic, is an encouraging step toward the greater goal of a plausible prebiotic pathway to RNA and the potential for an RNA world. However, this synthesis has led to a disparity in the methodology available for stepwise construction of the canonical pyrimidine and purine nucleotides. To address this problem, and further explore prebiotically accessible chemical systems, we have developed a high-yielding, aqueous, one-pot, multicomponent reaction that tethers masked-sugar moieties to prebiotically plausible purine precursors. A pH-dependent three-component reaction system has been discovered that utilizes key nucleotide synthons 2-aminooxazole and 5-aminoimidazoles, which allows the first divergent purine/pyrimidine synthesis to be proposed. Due to regiospecific aminoimidazole tethering, the pathway allows N9 purination only, thus suggesting the first prebiotically plausible mechanism for regiospecific N9 purination. {\textcopyright} 2010 American Chemical Society.},
author = {Powner, Matthew W. and Sutherland, John D. and Szostak, Jack W.},
doi = {10.1021/ja108197s},
issn = {15205126},
journal = {Journal of the American Chemical Society},
number = {46},
pages = {16677--16688},
pmid = {21043502},
title = {{Chemoselective multicomponent one-pot assembly of purine precursors in water}},
volume = {132},
year = {2010}
}
Downloads: 0
{"_id":"tPCoEGom4BMjh8xYH","bibbaseid":"powner-sutherland-szostak-chemoselectivemulticomponentonepotassemblyofpurineprecursorsinwater-2010","authorIDs":["38kWX4KNdemC8LePC","ACBJim4Zh8wmGTkCn","iMh9dPmru8GvT3mZ5","jAwdzkP7zNRfmiqix","srCdKMLurqnxjZxgi","x4TZgwqj3xbovb4re"],"author_short":["Powner, M. W.","Sutherland, J. D.","Szostak, J. W."],"bibdata":{"bibtype":"article","type":"article","abstract":"The recent development of a sequential, high-yielding route to activated pyrimidine nucleotides, under conditions thought to be prebiotic, is an encouraging step toward the greater goal of a plausible prebiotic pathway to RNA and the potential for an RNA world. However, this synthesis has led to a disparity in the methodology available for stepwise construction of the canonical pyrimidine and purine nucleotides. To address this problem, and further explore prebiotically accessible chemical systems, we have developed a high-yielding, aqueous, one-pot, multicomponent reaction that tethers masked-sugar moieties to prebiotically plausible purine precursors. A pH-dependent three-component reaction system has been discovered that utilizes key nucleotide synthons 2-aminooxazole and 5-aminoimidazoles, which allows the first divergent purine/pyrimidine synthesis to be proposed. Due to regiospecific aminoimidazole tethering, the pathway allows N9 purination only, thus suggesting the first prebiotically plausible mechanism for regiospecific N9 purination. © 2010 American Chemical Society.","author":[{"propositions":[],"lastnames":["Powner"],"firstnames":["Matthew","W."],"suffixes":[]},{"propositions":[],"lastnames":["Sutherland"],"firstnames":["John","D."],"suffixes":[]},{"propositions":[],"lastnames":["Szostak"],"firstnames":["Jack","W."],"suffixes":[]}],"doi":"10.1021/ja108197s","issn":"15205126","journal":"Journal of the American Chemical Society","number":"46","pages":"16677–16688","pmid":"21043502","title":"Chemoselective multicomponent one-pot assembly of purine precursors in water","volume":"132","year":"2010","bibtex":"@article{Powner2011b,\r\nabstract = {The recent development of a sequential, high-yielding route to activated pyrimidine nucleotides, under conditions thought to be prebiotic, is an encouraging step toward the greater goal of a plausible prebiotic pathway to RNA and the potential for an RNA world. However, this synthesis has led to a disparity in the methodology available for stepwise construction of the canonical pyrimidine and purine nucleotides. To address this problem, and further explore prebiotically accessible chemical systems, we have developed a high-yielding, aqueous, one-pot, multicomponent reaction that tethers masked-sugar moieties to prebiotically plausible purine precursors. A pH-dependent three-component reaction system has been discovered that utilizes key nucleotide synthons 2-aminooxazole and 5-aminoimidazoles, which allows the first divergent purine/pyrimidine synthesis to be proposed. Due to regiospecific aminoimidazole tethering, the pathway allows N9 purination only, thus suggesting the first prebiotically plausible mechanism for regiospecific N9 purination. {\\textcopyright} 2010 American Chemical Society.},\r\nauthor = {Powner, Matthew W. and Sutherland, John D. and Szostak, Jack W.},\r\ndoi = {10.1021/ja108197s},\r\nissn = {15205126},\r\njournal = {Journal of the American Chemical Society},\r\nnumber = {46},\r\npages = {16677--16688},\r\npmid = {21043502},\r\ntitle = {{Chemoselective multicomponent one-pot assembly of purine precursors in water}},\r\nvolume = {132},\r\nyear = {2010}\r\n}\r\n","author_short":["Powner, M. W.","Sutherland, J. D.","Szostak, J. W."],"key":"Powner2011b","id":"Powner2011b","bibbaseid":"powner-sutherland-szostak-chemoselectivemulticomponentonepotassemblyofpurineprecursorsinwater-2010","role":"author","urls":{},"metadata":{"authorlinks":{"powner, m":"https://bibbase.org/show?bib=benjaminthoma.github.io%2Fpubs.bib"}},"downloads":0,"html":""},"bibtype":"article","biburl":"http://pownerlab.com/pubs.bib","creationDate":"2020-06-26T14:21:50.271Z","downloads":0,"keywords":[],"search_terms":["chemoselective","multicomponent","one","pot","assembly","purine","precursors","water","powner","sutherland","szostak"],"title":"Chemoselective multicomponent one-pot assembly of purine precursors in water","year":2010,"dataSources":["9KEjTYsWfRuZ6w4rN","yni5TKeSthCoJvNNf","mdpZLZEzva4rFp2vp"]}