Synthesis and Application of a 5‘-Aldehyde Phosphoramidite for Covalent Attachment of DNA to Biomolecules

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 de...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-07, Vol.71 (15), p.5774-5777
Main Authors: Miduturu, Chandrasekhar V, Silverman, Scott K
Format: Article
Language:English
Subjects:
Aldehydes - chemical synthesis
Aldehydes - chemistry
Amines - chemistry
Analytical, structural and metabolic biochemistry
Biological and medical sciences
Carbohydrates. Nucleosides and nucleotides
Chemistry
DNA - chemistry
DNA - metabolism
Dna, deoxyribonucleoproteins
Exact sciences and technology
Fundamental and applied biological sciences. Psychology
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Nucleic acids
Nucleosides, nucleotides and oligonucleotides
Organic chemistry
Organophosphorus Compounds - chemical synthesis
Organophosphorus Compounds - chemistry
Preparations and properties
RNA - chemistry
RNA - metabolism
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo060723m