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5'-O-DMT-2'-O-tert-Butyldimethylsilyl-Inosine 3'-CE phosphoramidite
Antiviral and anticancer drug for cells infected with influenza A virus, herpes simplex virus type 2, and human lymphocytic leukemia cells.
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Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BRP-02183 | 1 g | $299 | In stock | |
| BRP-02183 | 2 g | $499 | In stock |
Catalog
BRP-02183
Synonyms
2'-O-tert-Butyldimethylsilyl-5'-O-DMT-inosine 3'-CE phosphoramidite; 2'-O-(tert-Butyldimethylsilyl)-3'-O-[(diisopropylamino)(2-cyanoethoxy)phosphino]-5'-O-(4,4'-dimethoxytrityl)inosine; Inosine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-[(1,1-dimethylethyl)dimethylsilyl]-, 3'-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite]; 5'-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-2'-O-[dimethyl(2-methyl-2-propanyl)silyl]inosine; DMT-2'-O-TBDMS-I-CE-Phosphoramidite; 5'-O-(4,4'-Dimethoxytrityl)-2'-O-(t-butyldimethylsilyl)-inosine-3'-cyanoethyl Phosphoramidite
CAS
261518-12-1
IUPAC Name
3-[[(2R,3R,4R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[tert-butyl(dimethyl)silyl]oxy-5-(6-oxo-1H-purin-9-yl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
Molecular Weight
885.07
Molecular Formula
C46H61N6O8PSi
Canonical SMILES
CC(C)N(C(C)C)P(OCCC#N)OC1C(OC(C1O[Si](C)(C)C(C)(C)C)N2C=NC3=C2N=CNC3=O)COC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC
InChI
InChI=1S/C46H61N6O8PSi/c1-31(2)52(32(3)4)61(57-27-15-26-47)59-40-38(58-44(41(40)60-62(10,11)45(5,6)7)51-30-50-39-42(51)48-29-49-43(39)53)28-56-46(33-16-13-12-14-17-33,34-18-22-36(54-8)23-19-34)35-20-24-37(55-9)25-21-35/h12-14,16-25,29-32,38,40-41,44H,15,27-28H2,1-11H3,(H,48,49,53)/t38-,40-,41-,44-,61?/m1/s1
InChIKey
ZUFMOUFQBYZIHB-JFOZTMRSSA-N
Boiling Point
866.8±75.0°C at 760 mmHg
Purity
≥97% by HPLC
Appearance
White to Off-white Powder
Storage
Store at RT
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.
