Synthesis of 3-guaninyl- and 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone nucleosides

Abdullah Saleh, John G. D'Angelo, Martha D. Morton, Jesse Quinn, Kendra Redden, Rafal W. Mielguz, Christopher Pavlik, Michael B. Smith

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Abstract

l- And d-glutamic acids, as well as trans-4-hydroxy-l-proline, are converted to the corresponding 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analog. The protecting group used to block the lactam nitrogen in key intermediates has a significant effect on the diastereoselectivity of the coupling reaction with adenine or guanine.

Original languageEnglish (US)
Pages (from-to)5574-5583
Number of pages10
JournalJournal of Organic Chemistry
Volume76
Issue number14
DOIs
Publication statusPublished - Jul 15 2011

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ASJC Scopus subject areas

  • Organic Chemistry

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Saleh, A., D'Angelo, J. G., Morton, M. D., Quinn, J., Redden, K., Mielguz, R. W., ... Smith, M. B. (2011). Synthesis of 3-guaninyl- and 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone nucleosides. Journal of Organic Chemistry, 76(14), 5574-5583. https://doi.org/10.1021/jo2004617