3731-55-3Relevant academic research and scientific papers
Diverse size approach to incorporate and extend highly fluorescent unnatural nucleotides into DNA
Le, Binh Huy,Koo, Ja Choon,Joo, Han Na,Seo, Young Jun
, p. 3591 - 3596 (2017/06/13)
We have prepared a series of size-diverse unnatural nucleotides containing fluorescent (dApyrTP, dUpyrTP, dUantTP, dUthiTP) and quencher (dUazoTP) units, as well as nucleotides presenting small functional groups (dAethTP, dAoctTP, dUethTP, dUiodTP), all based on deoxyadenosine and deoxyuridine, and examined their suitability for use in enzymatic incorporation and extension into DNA. We observed a size-dependence of the incorporation and extension capability (following the order dUiodTP?=?dUethTP?=?dUthiTP?>?dUazoTP?>?dUpyrTP?>?dUantTP) during primer extension. This result was supported by circular dichroism (CD) spectra, which revealed a trend in the different B-form DNA structures depending on the size of the unit at the 5-position of the deoxyuridine (dUiodTP?>?dUethTP?>?dUthiTP?>?dUpyrTP), obtained from the PCR products. Interestingly, dUthiTP could be incorporated and extended into long DNA strands during primer extension and even PCR amplification, with CD spectroscopy confirming a stable secondary B-form duplex DNA structure. We observed full-length extension products even when combining dUthiTP with a template containing 24 continuous dA units during the primer extension. Thus, we believe that dUthiTP is a promising fluorescent nucleotide for a diverse range of biological applications requiring multiple incorporation and extension directly without disruption of B-form DNA structures.
A new efficient stereoselective method for the synthesis of (E)-5-aminoallyl-pyrimidine-5′-triphosphates using palladium-catalyzed heck reaction
Kore, Anilkumar R.,Senthilvelan, Annamalai,Shanmugasundaram, Muthian,Sandoval, David,Pardo, Andrew
, p. 221 - 228 (2015/04/27)
An efficient overall two-step strategy for the synthesis of, starting from commercially available pyrimidine-5′-triphosphate is described. The method involves regioselective iodination of pyrimidine-5′-triphosphate, followed by the palladium-catalyzed Heck coupling with allylamine. The catalytic reaction is highly stereoselective and compatible with many functional groups present in the reactants.
Rigid, conjugated, fluoresceinated thymidine triphosphates: Syntheses and polymerase mediated incorporation into DNA analogues
Thoresen, Lars H.,Jiao, Guan-Sheng,Haaland, Wade C.,Metzker, Michael L.,Burgess, Kevin
, p. 4603 - 4610 (2007/10/03)
Syntheses of a unique set of energy transfer dye labeled nucleoside triphosphates, compounds 1-3, are described. Attempts to prepare these compounds were only successful if the triphosphorylation reaction was performed before coupling the dye to the nucle
