110522-75-3

Basic information

• Product Name: IBU-DEOXYCYTIDINE
• Synonyms: NIBU-2'-DC;N4-ISOBUTYRYLDEOXYCYTIDINE;N4-(ISOBUTYRYL)-2'-DEOXYCYTIDINE;IBU-DEOXYCYTIDINE;N-Isobutyryl-2'-deoxycytidine;N4-ISOBUTYLRYL-2''-DEOXYCYTIDINE;ibu-dC;2'-Deoxy-N2-isobutyryl-a-cytidine
• CAS NO: 110522-75-3
• Molecular Formula: C₁₃H₁₉N₃O₅
• Molecular Weight: 297.31
• Product Categories: Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 110522-75-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.49 g/cm³
• Refractive Index: 1.641
• Storage Temp.: −20°C
• PKA: 10.03±0.20(Predicted)
• CAS DataBase Reference: IBU-DEOXYCYTIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: IBU-DEOXYCYTIDINE(110522-75-3)
• EPA Substance Registry System: IBU-DEOXYCYTIDINE(110522-75-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 110522-75-3(Hazardous Substances Data)

Usage

General Description

IBU-deoxycytidine is a chemical compound often referenced in biochemical research. Its IUPAC name is 4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-pyrimidin-2-one, indicating its structural composition. It is commonly utilized in scientific studies related to DNA replication, repair, and transcription due to its resemblance to naturally occurring nucleosides. Despite its frequent usage in research, there is little information available on its potential toxic or hazardous effects in humans or the environment. Therefore, it's critical to handle this chemical with care and follow safety protocols when in use.

InChI:InChI=1/C13H19N3O5/c1-7(2)12(19)14-10-3-4-16(13(20)15-10)11-5-8(18)9(6-17)21-11/h3-4,7-9,11,17-18H,5-6H2,1-2H3,(H,14,15,19,20)

Upstream product

• 110522-80-0 Isobutyric acid (2R,3S,5R)-5-(4-isobutyrylamino-2-oxo-2H-pyrimidin-1-yl)-2-isobutyryloxymethyl-tetrahydro-furan-3-yl ester 
• 97-72-3 2-Methylpropionic anhydride 
• 951-77-9 2'-Deoxycytidine 

Downstream Products

• 100898-62-2 N-(1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)isobutyramide 
• 22882-02-6 4-methylamino-1-(β-D-2-deoxyribofuranosyl)pyrimidin-2(1H)-one 
• 951-77-9 2'-Deoxycytidine 
• 110808-24-7 Phosphoric acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(4-isobutyrylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester; compound with triethyl-amine 
• 110522-84-4 N⁴-isobutyryl-2'-deoxycytidine-3'-diisopropylaminocyanoethyl phosphoramidite 

Relevant articles and documents

Ultrafast cleavage and deprotection of oligonucleotides synthesis and use of C(Ac) derivatives

We have investigated the use of alkylamines as fast cleavage and deprotection reagents for the solid phase synthesis of oligonucleotides and found methylamine/ammonium hydroxide (or methylamine) as an efficient reagent. The transamination side product formed with the commonly used dC(b2) has been eliminated by the use of dC(Ac) phosphoramidite. This system has successfully been used in the synthesis of oligonucleotides and oligonucleoside phosphorothioates. DMT dC(Ac) hydrogen phosphonate and DMT ribo C(Ac)-2'-OMe phosphoramidite also have been prepared and used in the synthesis of oligonucleotides.

FACILE REMOVAL OF NEW BASE PROTECTING GROUPS USEFUL IN OLIGONUCLEOTIDE SYNTHESIS

New base protecting groups are proposed in place of benzoyl and isobutyryl groups.They are phenoxy acetyl for adenine and guanine and isobutyryl for cytosine.They are cleaved in aqueous ammonia in a shorter time at lower temperature.These easily removable groups are useful in the synthesis of modified oligonucleotides, containing fragile bases.