A novel structural class of photoswitchable oligonucleotide

Research output: Contribution to journalArticle

Authors

  • EE Smith
  • JN McClean
  • LA Cooke
  • M McCourt
  • MM Fabani
  • JS Vyle

Colleges, School and Institutes

Abstract

Directed Michaelis-Arbuzov reactions of support-bound internucleotide O-benzyl- or O-methyl-phosphite triesters with meta-phenylazobenzylamine or alkane-/glycol-linked alpha,omega-diamines were effected in the presence of iodine. The corresponding tritylated phosphoramidate-linked 11-mers were fully deprotected and released from the support under standard conditions and the fast- and slow-diastereoisomers of both the E- and the Z-meta-phenylazobenzyl-appended oligomers were readily resolved by RP-HPLC. The primary amine-functionalised oligonucleotides were either purified, detritylated and then finally treated with N-hydroxysuccinimidyl carboxylic acid ester derivatives of photoswitchable moieties (Route A) or first derivatised and then subsequently purified and detritylated (Route B). This latter route enabled resolution of fast- and slow-isomers of the trityl-on oligomers bearing novel photoswitchable azopyridine or 9-alkoxyanthracene moieties using RP-HPLC, following which the pure diastereoisomers were detritylated and characterised by MALDI-MS. (C) 2007 Elsevier Ltd. All rights reserved.

Details

Original languageEnglish
Pages (from-to)6569-6572
Number of pages4
JournalTetrahedron Letters
Volume48
Publication statusPublished - 10 Sep 2007