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

Research output: Contribution to journalArticle

10 Scopus citations


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
Issue number14
Publication statusPublished - Jul 15 2011


ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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.