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N6-Benzoyl-2'-deoxy-5'-O-DMT-2'-fluoroadenosine 3'-CE phosphoramidite
N6-Benzoyl-2'-deoxy-5'-O-DMT-2'-fluoroadenosine 3'-CE phosphoramidite can be used to incorporate 2-fluoro modified nucleotides into oligonucleotides, improving metabolic stability.
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Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BRP-02170 | 10 g | $1449 | In stock |
Catalog
BRP-02170
Synonyms
2'-Fluoro-dA CEP; 2'-Fluoro-Bz-A-CEP; N6-Benzoyl-2'-deoxy-5'-O-DMT-2'-fluoro-D-adenosine 3'-CE phosphoramidite; N6-Benzoyl-5'-O-DMT-2'-fluoro-2'-deoxyadenosine 3'-CE phosphoramidite; DMT-2'-F-dA(Bz)-CE-Phosphoramidite; N6-Bz-5'-O-(4,4'-dimethoxytrityl)-2'-fluoro-2'-deoxyadenosine-3'-CE-Phosphoramidite; N6-Benzoyl-5'-O-(4,4'-Dimethoxytrityl)-2'-deoxy-2'-fluoroadenosine-3'-O-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite
CAS
136834-22-5
IUPAC Name
N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-3-fluorooxolan-2-yl]purin-6-yl]benzamide
Molecular Weight
875.95
Molecular Formula
C47H51FN7O7P
Canonical SMILES
CC(C)N(C(C)C)P(OCCC#N)OC1C(OC(C1F)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/C47H51FN7O7P/c1-31(2)55(32(3)4)63(60-27-13-26-49)62-42-39(61-46(40(42)48)54-30-52-41-43(50-29-51-44(41)54)53-45(56)33-14-9-7-10-15-33)28-59-47(34-16-11-8-12-17-34,35-18-22-37(57-5)23-19-35)36-20-24-38(58-6)25-21-36/h7-12,14-25,29-32,39-40,42,46H,13,27-28H2,1-6H3,(H,50,51,53,56)/t39-,40-,42-,46-,63?/m1/s1
InChIKey
VCCMVPDSLHFCBB-MSIRFHFKSA-N
Purity
≥98% by HPLC
Appearance
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.
