5'-O-DMT-N4-Acetyl-2'-fluoro-2'-arabinofuranosyl-deoxycytidine 3'-CE phosphoramidite
5'-O-DMT-N4-Acetyl-2'-fluoro-2'-arabinofuranosyl-deoxycytidine 3'-CE phosphoramidite is a crucial reagent extensively used in the biomedical industry for the synthesis of nucleosides and nucleotides. This product plays a significant role in the development of therapeutic drugs targeting various diseases, including viral infections and cancer. With its unique properties, it enables researchers to design and fabricate novel nucleoside analogs with potential antiviral and anticancer activities, contributing to advancements in biomedicine.
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Synonyms
2'-F-2'-ara-Ac-dC Phosphoramidite; 4-Acetamido-1-{5-O-[bis(4-methoxyphenyl)(phenyl)methyl]-3-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-2-deoxy-2-fluoro-β-D-arabinofuranosyl}-2(1H)-pyrimidinone; 2(1H)-Pyrimidinone, 4-(acetylamino)-1-[5-O-[bis(4-methoxyphenyl)phenylmethyl]-3-O-[[bis(1-methylethyl)amino](2-cyanoethoxy)phosphino]-2-deoxy-2-fluoro-β-D-arabinofuranosyl]-; N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-deoxy-2'-fluorocytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
IUPAC Name
N-[1-[(2R,3S,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 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-AXLBFYELSA-N
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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