Synthesis and application of a 5′-aldehyde phosphoramidite for covalent attachment of DNA to biomolecules

Chandrasekhar V. Miduturu, Scott K Silverman

Research output: Contribution to journalArticle

Abstract

We recently reported the use of covalently attached DNA as a structural constraint for rational control of macromolecular conformation. Reductive amination was employed to attach each strand of the duplex DNA constraint to RNA, utilizing an aldehyde tethered to the 5′-terminus of the DNA. Here we describe the synthesis of a thymidine phosphoramidite that has the 5′-tethered aldehyde masked as a 1,2-diol. We also describe optimized reductive amination conditions for linking 5′-aldehyde-DNA with 2′-amino-2′-deoxy-RNA. These procedures should be generally applicable for attaching DNA to biomolecules.

Original languageEnglish (US)
Pages (from-to)5774-5777
Number of pages4
JournalJournal of Organic Chemistry
Volume71
Issue number15
DOIs
StatePublished - Jul 21 2006

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Biomolecules
Aldehydes
Amination
DNA
RNA
Thymidine
Conformations
phosphoramidite

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and application of a 5′-aldehyde phosphoramidite for covalent attachment of DNA to biomolecules. / Miduturu, Chandrasekhar V.; Silverman, Scott K.

In: Journal of Organic Chemistry, Vol. 71, No. 15, 21.07.2006, p. 5774-5777.

Research output: Contribution to journalArticle

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