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5'-O-DMT-2'-O-methyl-5-methyluridine 3'-CE phosphoramidite
5'-O-DMT-2'-O-methyl-5-methyluridine 3'-CE phosphoramidite is a novel antiviral and anticancer agent.
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Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BRP-02165 | 500 mg | $198 | In stock |
Catalog
BRP-02165
Synonyms
5'-O-DMT-5-Methy-2'-O-methyluridine 3'-CE phosphoramidite; 5'-O-DMT-2'-O-methyl-5-methyl-D-uridine 3'-CE phosphoramidite; 2'-O-Methyl-5-methyl-U CEP; 5-O-(4,4'-dimethoxytrityl)-3-O-(diisopropylamino-2-cyanoethoxyphosphanyl)-1-deoxy-2-O-methyl-1-thymin-1-yl-beta-D-ribo-pentofuranose; 5-Methyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-uridine-3'-cyanoethyl phosphoramidite
CAS
153631-20-0
IUPAC Name
3-[[(2R,3R,4R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-methoxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
Molecular Weight
774.86
Molecular Formula
C41H51N4O9P
Canonical SMILES
CC1=CN(C(=O)NC1=O)C2C(C(C(O2)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)OP(N(C(C)C)C(C)C)OCCC#N)OC
InChI
InChI=1S/C41H51N4O9P/c1-27(2)45(28(3)4)55(52-24-12-23-42)54-36-35(53-39(37(36)50-8)44-25-29(5)38(46)43-40(44)47)26-51-41(30-13-10-9-11-14-30,31-15-19-33(48-6)20-16-31)32-17-21-34(49-7)22-18-32/h9-11,13-22,25,27-28,35-37,39H,12,24,26H2,1-8H3,(H,43,46,47)/t35-,36-,37-,39-,55?/m1/s1
InChIKey
GMJRPRHRYILEOK-VNZAIEIISA-N
Purity
≥98% by HPLC
Storage
Store at -20 °C
Related CAS
168611-14-1 (R-isomer) 168611-18-5 (S-isomer)
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.
