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You are at : All > Oligonucleotides > Custom Oligonucleotide Components > Custom Oligonucleotide Components by Property > Isomorphic-Intrinsically Fluorescent

Isomorphic-Intrinsically Fluorescent

The non-emissive nature of the nucleobases found in natural nucleic acids has triggered the development of emissive nucleoside analogs. When carefully designed and employed, fluorescent nucleosides, nucleotides and oligonucleotides serve an unparalleled role in exploring fundamental biochemical transformations and facilitate the fabrication of biophysical and discovery assays. A key criterion for the design and successful implementation of such probes is to minimize structural and functional perturbation, which is an inevitable consequence of replacing any native residue with a synthetic probe. This important constraint has led to the development of intrinsically emissive nucleoside analogs that display high structural resemblance to their native counterparts, a characteristic commonly described as isomorphicity.

Isomorphic nucleobase analogs are heterocycles that closely resemble the corresponding natural nucleobases with respect to their overall dimensions, hydrogen bonding patterns, and ability to form isostructural W-C base pairs. A clear advantage of these analogs is their strong similarity to the native nucleosides and minimally perturbing nature, when compared with the diverse analogs discussed above. Since favorable photophysical characteristics, such as red-shifted absorption and high emission quantum efficiencies, are typically associated with significant structural perturbation and extended conjugation, isomorphic fluorescent nucleosides are the most challenging to design.
 
1. Sinkeldam RW, Greco NJ, Tor Y. Fluorescent analogs of biomolecular building blocks: design, properties, and applications. Chem Rev. 2010 May 12;110(5):2579-619.
2. Okamoto A, Saito Y, Saito I. Design of base-discriminating fluorescent nucleosides. J Photochem Photobiol C Photo. 2005 Oct: 6(2-3): 108-122.
3. Wilson JN, Kool ET. Fluorescent DNA base replacements: Reporters and sensors for biological systems. Org Biomol Chem. 2006 Dec 7;4(23):4265-74.
4. Dodd DW, Hudson RHE. Intrinsically Fluorescent Base-Discriminating Nucleoside Analogs. Mini Rev Org Chem. 2009 Nov; 6(4): 378-391.
5. Wilhelmsson LM. Fluorescent nucleic acid base analogues. Q Rev Biophys. 2010 May;43(2):159-83.
6. Kimoto M, Cox RS 3rd, Hirao I. Unnatural base pair systems for sensing and diagnostic applications. Expert Rev Mol Diagn. 2011 Apr;11(3):321-31.
7. Greco NJ, Tor Y. Simple fluorescent pyrimidine analogues detect the presence of DNA abasic sites. J Am Chem Soc. 2005 Aug 10;127(31):10784-5.
8. Tor Y, Del Valle S, Jaramillo D, Srivatsan SG, Rios A, Weizman H. Designing New Isomorphic Fluorescent Nucleobase Analogues: The Thieno[3,2-d]pyrimidine Core. Tetrahedron. 2007 Apr 23; 63(17); 3608-3614.
9. Tor Y. Exploring RNA-ligand interactions. Pure Appl Chem. 2009 Jan 1; 81(2); 1365-3075.

 

2-Aminopurine-2'-deoxyriboside
Etheno-2'-deoxyadenosine
2-Aminopurine-riboside
2-Aminopurine-2'-O-methylriboside
Pyrrolo-2'-deoxycytidine
Thienoguanosine
Thienouridine
Thienocytidine
2'-Deoxythienoguanosine


 

 


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