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5'-O-DMT-N4-Benzoyl-5-methyl-2'-O-methylcytidine 3'-CE phosphoramidite
5'-O-DMT-N4-Benzoyl-5-methyl-2'-O-methylcytidine 3'-CE phosphoramidite is a phosphoramidite analogue with antiviral, anticancer and antimalarial properties.
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Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BRP-02179 | 1 g | $519 | In stock |
Catalog
BRP-02179
Synonyms
N4-Benzoyl-5-methyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-cytidine-3'-cyanoethyl phosphoramidite; 2'-OMe-N6-Bz-5-Me-C Phosphoramidite; 5'-DMT-N4-Bz-2'-OMe-5-Me-C phosphoramidite; DMT-2'-OME-dC(Bz)-CE-Phosphoramidite; N-Benzoyl-5'-O-[bis(4-methoxyphenyl)(phenyl)methyl]-3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-5-methyl-2'-O-methylcytidine; 5-Me-DMT-2'-O-Me-C(Bz)-CE-Phosphoramidite; 5'-O-DMT-2'-O-Me-MeC(Bz)-3'-CE-Phosphoramidite
CAS
166593-57-3
IUPAC Name
N-[1-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-3-methoxyoxolan-2-yl]-5-methyl-2-oxopyrimidin-4-yl]benzamide
Molecular Weight
877.98
Molecular Formula
C48H56N5O9P
Canonical SMILES
CC1=CN(C(=O)N=C1NC(=O)C2=CC=CC=C2)C3C(C(C(O3)COC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC)OP(N(C(C)C)C(C)C)OCCC#N)OC
InChI
InChI=1S/C48H56N5O9P/c1-32(2)53(33(3)4)63(60-29-15-28-49)62-42-41(61-46(43(42)58-8)52-30-34(5)44(51-47(52)55)50-45(54)35-16-11-9-12-17-35)31-59-48(36-18-13-10-14-19-36,37-20-24-39(56-6)25-21-37)38-22-26-40(57-7)27-23-38/h9-14,16-27,30,32-33,41-43,46H,15,29,31H2,1-8H3,(H,50,51,54,55)/t41-,42-,43-,46-,63?/m1/s1
InChIKey
GIWYLFDPXKHBKT-AENBYTAOSA-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.
