5'-O-DMT-2'-O-tert-Butyldimethylsilyl-N6-Benzoyl-8-Iodoadenosine 3'-CE phosphoramidite
5'-O-DMT-2'-O-tert-Butyldimethylsilyl-N6-Benzoyl-8-Iodoadenosine 3'-CE phosphoramidite, a critical and indispensable reagent in the highly esteemed biomedical industry, manifests its profound significance in the realm of modified nucleic acids synthesis. Its exceptional utility primarily lies in its adeptness for effectuating the introduction of the esteemed 5'-O-DMT-2'-O-tert-Butyldimethylsilyl-N6-Benzoyl-8-Iodoadenosine moiety during phosphoramidite-mediated DNA synthesis. This unparalleled product unveils a wealth of opportunities within the sphere of nucleic acid-based therapeutic development, acting as a fulcrum for groundbreaking research directed towards unravelling the complexities of diverse disease entities and optimizing drug targeting strategies.
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Synonyms
8-I-rA phosphoramidite; DMT-2'-O-TBDMS-8-I-A(Bz)-CE-Phosphoramidite; N6-Benzoyl-2'-O-tert-butyldimethylsilyl-5'-O-DMT-8-Iodoadenosine 3'-CE phosphoramidite; 5'-O-DMT-2'-O-TBDMS-8-I-A(Bz)-3'-CE-Phosphoramidite
IUPAC Name
(2R,3R,4R,5R)-5-(6-benzamido-8-iodo-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite
Molecular Formula
C53H65IN7O8PSi
InChI
InChI=1S/C53H65IN7O8PSi/c1-35(2)61(36(3)4)70(66-32-18-31-55)68-45-43(33-65-53(38-21-16-13-17-22-38,39-23-27-41(63-8)28-24-39)40-25-29-42(64-9)30-26-40)67-50(46(45)69-71(10,11)52(5,6)7)60-48-44(58-51(60)54)47(56-34-57-48)59-49(62)37-19-14-12-15-20-37/h12-17,19-30,34-36,43,45-46,50H,18,32-33H2,1-11H3,(H,56,57,59,62)/t43-,45-,46-,50-,70?/m1/s1
InChIKey
YIYILOGGUDEHPF-UFCBNZGASA-N
Chemical Structure:
Reference Reading
1. A universal, photocleavable DNA base: nitropiperonyl 2'-deoxyriboside
M C Pirrung, X Zhao, S V Harris. J Org Chem. 2001 Mar 23;66(6):2067-71. doi: 10.1021/jo001594r.
A universal, photochemically cleavable DNA base analogue would add desirable versatility to a number of methods in molecular biology. A novel C-nucleoside, nitropiperonyl deoxyriboside (NPdR, P), has been investigated for this purpose. NPdR can be converted to its 5'-DMTr-3'-CE-phosphoramidite and was incorporated into pentacosanucleotides by conventional synthesis techniques. The destabilizing effect on hybrid formation with a complementary strand when this P base opposes A, T, and G was found to be 3-5 kcal/mol, but 9 kcal/mol when it opposes C. Brief irradiation (lambda > 360 nm, 20 min) of DNA containing the P base and piperidine treatment causes strand cleavage giving the 3'- and 5'-phosphates. Two significant recent interests, universal/non-hydrogen-bonding base analogues and photochemical backbone cleavage, have thus been combined in a single molecule that serves as a light-based DNA scissors.
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