Photolabile thymidine cleavable with a 532 nanometer laser

The synthesis and characterization of a novel 3′p-hydroxyphenacyl-caged thymidine bearing a 5′N,N-diisopropylcyanoethylphosphoramidite is presented representing a new methodology for the photoregulation of PCR and gene expression. Solid phase oligonucleotide synthesis affords a primer blocked at the...

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Bibliographic Details
Published in:Tetrahedron letters 2011-09, Vol.52 (39), p.4989-4991
Main Authors: Pickens, Chad J., Gee, Kyle R.
Format: Article
Language:English
Subjects:
Analytical, structural and metabolic biochemistry
Biological and medical sciences
Blocking
Caged thymidine
Carbohydrates. Nucleosides and nucleotides
Chemistry
Dna, deoxyribonucleoproteins
Exact sciences and technology
Fundamental and applied biological sciences. Psychology
General and physical chemistry
Lasers
Nucleic acids
Nucleosides, nucleotides and oligonucleotides
Oligonucleotides
Organic chemistry
p-Hydroxyphenacyl
PCR
Phosphoramidite
Photochemistry
Photolysis
Physical chemistry of induced reactions (with radiations, particles and ultrasonics)
Preparations and properties
Solid phases
Synthesis (chemistry)
Tetrahedrons
Thymidine
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Summary:The synthesis and characterization of a novel 3′p-hydroxyphenacyl-caged thymidine bearing a 5′N,N-diisopropylcyanoethylphosphoramidite is presented representing a new methodology for the photoregulation of PCR and gene expression. Solid phase oligonucleotide synthesis affords a primer blocked at the 3′ position, which could function as a phototrigger for polymerase activity. The caging group exhibits quantitative photolysis in 15s using a 532nm green hand laser.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.07.052