Strathprints logo
Strathprints Home | Open Access | Browse | Search | User area | Copyright | Help | Library Home | SUPrimo

Oligonucleotide conjugation to a cell-penetrating (tat) peptide by diels-alder cycloaddition

Steven, V. and Graham, D. (2008) Oligonucleotide conjugation to a cell-penetrating (tat) peptide by diels-alder cycloaddition. Organic and Biomolecular Chemistry, 6 (20). pp. 3781-3787. ISSN 1477-0520

Full text not available in this repository. (Request a copy from the Strathclyde author)

Abstract

Modifed oligonucleotides are routinely employed as analytical probes for use in diagnostics, e.g. in the examination of specific RNA sequences for infectious diseases, however, a major limiting factor in oligonucleotide-based diagnostics is poor cellular uptake of naked oligonucleotides. This problem can be overcome by covalent attachment of a so-called 'cell-penetrating peptide' to form an oligonucleotide peptide conjugate. Stepwise solid phase synthesis of such a conjugate is difficult and expensive due to the conflicting chemistries of oligonucleotides and peptides. A simple approach to overcome this is post-synthetic conjugation. Diels-Alder cycloaddition is an attractive methodology for oligonucleotide peptide conjugation; the reaction is fast, chemoselective and the reaction rate is greatly enhanced in aqueous media - ideal conditions for biological moieties. An oligodeoxyribonucleotide sequence has been derivatised with a series of dienes at the 5′-terminus, using a series of unique dienyl-modified phosphoramidites, and investigation into the effect of diene type on the efficiency of conjugation, using Diels-Alder cycloaddition with a maleimido-derivatised cell-penetrating (TAT) peptide, has been performed. This led to the observation that the optimal diene for conjugation was cyclohexadiene, allowing conjugation of oligodeoxyribonucleotides to a cell-penetrating peptide by Diels-Alder cycloaddition for the first time. (Taken from Swetswise web site: http://www.swetswise.com/eAccess/viewAbstract.do?articleID=38485673)

Item type: Article
ID code: 17022
Notes: http://suprimo.lib.strath.ac.uk/primo_library/libweb/action/search.do?scp.scps=scope%3A(SU)&srt=rank&tab=local&mode=Basic&dum=true&fn=search&frbg=&dstmp=1270647806478&dscnt=0&ct=search&vid=SUVU01&indx=1&vl(freeText0)=Organic%20%26%20biomolecular%20chemistry&vl(54032236UI0)=lsr02&vl(96071691UI1)=all_items
Keywords: oligonucleotide, conjugation, cell-penetrating (tat) peptide, diels-alder cycloaddition, Chemistry, Physical and theoretical chemistry, Biochemistry, Organic Chemistry, Physical and Theoretical Chemistry
Subjects: Science > Chemistry
Science > Chemistry > Physical and theoretical chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Related URLs:
Depositing user: Strathprints Administrator
Date Deposited: 07 Apr 2010 14:53
Last modified: 05 Sep 2014 02:43
URI: http://strathprints.strath.ac.uk/id/eprint/17022

Actions (login required)

View Item