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5'-O-DMT-N4-Acetyl-2'-fluoro-2'-deoxy-cytidine 3'-CE phosphoramidite - CAS 159414-99-0
Catalog number: BRA-0225'-O-DMT-N4-Acetyl-2'-fluoro-2'-deoxy-cytidine 3'-CE phosphoramidite is a phosphoramidite compound used to introduce 2-fluoro-modified nucleotides into oligonucleotides.
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Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BRA-022 | 10 g | $838 | In stock |
Synonyms
N4-Acetyl-2'-deoxy-5'-O-DMT-2'-fluorocytidine 3'-CE phosphoramidite; 2'-F-Ac-dC CE phosphoramide; 2'-F-Ac-dC Phosphoramidite; Dmt-2'-f-dc(ac) amidite; DMT-2'Fluoro-dC(ac) Phosphoramidite
CAS
159414-99-0
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-fluorooxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
Molecular Weight
789.83
Molecular Formula
C41H49FN5O8P
Canonical SMILES
CC(C)N(C(C)C)P(OCCC#N)OC1C(OC(C1F)N2C=CC(=NC2=O)NC(=O)C)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC
InChI
InChI=1S/C41H49FN5O8P/c1-27(2)47(28(3)4)56(53-25-11-23-43)55-38-35(54-39(37(38)42)46-24-22-36(44-29(5)48)45-40(46)49)26-52-41(30-12-9-8-10-13-30,31-14-18-33(50-6)19-15-31)32-16-20-34(51-7)21-17-32/h8-10,12-22,24,27-28,35,37-39H,11,25-26H2,1-7H3,(H,44,45,48,49)/t35-,37-,38-,39-,56?/m1/s1
InChIKey
CNFKJHKDSRXNFL-UTXREMQHSA-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.
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