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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 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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Catalog
BRP-02188
Synonyms
DMT-2'-O-TBDMS-N2-iBu-2-aminoadenosine phosphoramidite; DMT-2'-O-TBDMS-N2-iBu-A-CE-Phosphoramidite; 5'-O-DMTr-2'-O-TBDMS-N2-iBu-A-3'-CE-Phosphoramidite; 5'-O-(4,4-Dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]-N2-isobutyryladenosine-3'-(2-cyanoethyl-N,N-diisopropyl)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
InChI
InChI=1S/C50H69N8O8PSi/c1-32(2)46(59)56-48-54-44(52)41-45(55-48)57(31-53-41)47-43(66-68(12,13)49(7,8)9)42(65-67(63-29-17-28-51)58(33(3)4)34(5)6)40(64-47)30-62-50(35-18-15-14-16-19-35,36-20-24-38(60-10)25-21-36)37-22-26-39(61-11)27-23-37/h14-16,18-27,31-34,40,42-43,47H,17,29-30H2,1-13H3,(H3,52,54,55,56,59)/t40-,42-,43-,47-,67?/m1/s1
InChIKey
NKCWJSASWRVTLE-FTZVBZPOSA-N
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.
