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5'-O-DMT-2'-O-TBDMS-N6-Benzoyl-L-Adenosine 3'-CE phosphoramidite
5'-O-DMT-2'-O-TBDMS-N6-Benzoyl-L-Adenosine 3'-CE phosphoramidite is a crucial reagent used in the synthesis of oligonucleotides for biomedical research. It enables the efficient introduction of N6-benzoyl-L-Adenosine residues into the oligonucleotide chain, thus allowing the study of adenosine-modified nucleic acids. This product finds applications in drug discovery, gene therapy, and understanding diseases related to adenosine signaling pathways.
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Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BRP-02180 | 1 g | $990 | In stock |
Catalog
BRP-02180
Synonyms
Benzamide, N-[9-[5-O-[bis(4-methoxyphenyl)phenylmethyl]-3-O-[[bis(1-methylethyl)amino](2-cyanoethoxy)phosphino]-2-O-[(1,1-dimethylethyl)dimethylsilyl]-β-L-ribofuranosyl]-9H-purin-6-yl]-; N-Benzoyl-9-{5-O-[bis(4-methoxyphenyl)(phenyl)methyl]-3-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-2-O-[dimethyl(2-methyl-2-propanyl)silyl]-β-L-ribofuranosyl}-9H-purin-6-amine; DMT-2'-O-TBDMS-L-rA(Bz) Phosphoramidite; 5'-O-DMTr-2'-O-TBDMS-L-A(Bz)-3'-CE-Phosphoramidite; N6-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(t-butyl-dimethylsilyl)-L-adenosine-3'-cyanoethyl Phosphoramidite
CAS
1803193-36-3
IUPAC Name
N-[9-[(2S,3S,4S,5S)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[tert-butyl(dimethyl)silyl]oxy-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]purin-6-yl]benzamide
Molecular Weight
988.21
Molecular Formula
C53H66N7O8PSi
Canonical SMILES
CC(C)N(C(C)C)P(OCCC#N)OC1C(OC(C1O[Si](C)(C)C(C)(C)C)N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)COC(C5=CC=CC=C5)(C6=CC=C(C=C6)OC)C7=CC=C(C=C7)OC
InChI
InChI=1S/C53H66N7O8PSi/c1-36(2)60(37(3)4)69(65-32-18-31-54)67-46-44(33-64-53(39-21-16-13-17-22-39,40-23-27-42(62-8)28-24-40)41-25-29-43(63-9)30-26-41)66-51(47(46)68-70(10,11)52(5,6)7)59-35-57-45-48(55-34-56-49(45)59)58-50(61)38-19-14-12-15-20-38/h12-17,19-30,34-37,44,46-47,51H,18,32-33H2,1-11H3,(H,55,56,58,61)/t44-,46-,47-,51-,69?/m0/s1
InChIKey
FFXHNCNNHASXCT-XMSTWNTJSA-N
Purity
≥98% by HPLC
Appearance
White to off-white powder
Storage
Store at -20 °C
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.
