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 journalArticlepeer-review

10 Scopus citations

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
StatePublished - Jul 15 2011

ASJC Scopus subject areas

  • Organic Chemistry

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