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5'-O-DMT-2'-O-methyluridine 3'-CE phosphoramidite - CAS 110764-79-9
Catalog number: BRA-0035'-O-DMT-2'-O-methyluridine 3'-CE phosphoramidite is a phosphoramidite reagent used to introduce 2-O-methyl modified U nucleotide into oligonucleotides.
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Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BRA-003 | 5 g | $239 | In stock |
Synonyms
5'-O-(4,4'-Dimethoxytrityl)-2'-O-methyluridine-3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite; 2'-Deoxy-2'-O-Me-5'-O-DMT-Uridine-3'-CED Phosphoramidite; 2'-OMe-U-CEP; 5'-Dimethoxytrityl-Uridine, 2'-O-methyl, 3'-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite; 2'-O-Methyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)uridine
CAS
110764-79-9
IUPAC Name
3-[[(2R,3R,4R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(2,4-dioxopyrimidin-1-yl)-4-methoxyoxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
Molecular Weight
760.81
Molecular Formula
C40H49N4O9P
Canonical SMILES
CC(C)N(C(C)C)P(OCCC#N)OC1C(OC(C1OC)N2C=CC(=O)NC2=O)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC
InChI
InChI=1S/C40H49N4O9P/c1-27(2)44(28(3)4)54(51-25-11-23-41)53-36-34(52-38(37(36)49-7)43-24-22-35(45)42-39(43)46)26-50-40(29-12-9-8-10-13-29,30-14-18-32(47-5)19-15-30)31-16-20-33(48-6)21-17-31/h8-10,12-22,24,27-28,34,36-38H,11,25-26H2,1-7H3,(H,42,45,46)/t34-,36-,37-,38-,54?/m1/s1
InChIKey
UVUOJOLPNDCIHL-XKZJCBTISA-N
Purity
≥95%
Appearance
White to Off-white Powder
Storage
Store at 2-8°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.
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