5'-O-DMT-N4-Acetyl-2'-fluoro-2'-arabinofuranosyl-deoxycytidine 3'-CE phosphoramidite

Catalog number: BRA-048

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.

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

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 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-AXLBFYELSA-N

Purity

≥97% by HPLC

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.