5'-O-DMT-2'-O-TBDMS-N2-ibu-2-aminoadenosine 3'-CE phosphoramidite

5'-O-DMT-2'-O-TBDMS-N2-ibu-2-aminoadenosine 3'-CE phosphoramidite

Catalog number: BRA-043

5'-O-DMT-2'-O-TBDMS-N2-ibu-2-aminoadenosine 3'-CE phosphoramidite is a compound assuming a pivotal role in oligonucleotide modification. Employed extensively in diverse applications such as targeted drug delivery systems, this phosphoramidite plays a pioneering role in the quest for refined therapeutics that combat distinctive ailments like cancer and genetic anomalies.

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Synonyms
DMT-2'-O-TBDMS-N2-ibu-2-aminoadenosine phosphoramidite
IUPAC Name
(2R,3R,4R,5R)-5-(6-amino-2-isobutyramido-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite
Molecular Weight
969.21
Molecular Formula
C50H69N8O8PSi
Purity
≥97% by HPLC

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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