80681-25-0

Basic information

• Product Name: N2-Isobutyryl-2'-Fluoro-2'-deoxyguanosine
• Synonyms: N2-Isobutyryl-2'-Fluoro-2'-deoxyguanosine;iBu-2'-F-dG;Guanosine, 2'-deoxy-2'-fluoro-N-(2-Methyl-1-oxopropyl)-;2'-Deoxy-2'-fluoro-N-(2-methyl-1-oxopropyl)guanosine;2'-Deoxy-2'-fluoro-N-isobutyrylguanosine;2'-Deoxy-N2-isobutyryl-2'-fluoroguanosine;N-(9-((2R,3R,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide;N2-isobutyryl-2'-deoxy-2'-fluoroguanosine
• CAS NO: 80681-25-0
• Molecular Formula: C₁₄H₁₈FN₅O₅
• Molecular Weight: 355.3216232
• Mol File: 80681-25-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 1.78±0.1 g/cm3(Predicted)
• PKA: 9.16±0.20(Predicted)
• CAS DataBase Reference: N2-Isobutyryl-2'-Fluoro-2'-deoxyguanosine(CAS DataBase Reference)
• NIST Chemistry Reference: N2-Isobutyryl-2'-Fluoro-2'-deoxyguanosine(80681-25-0)
• EPA Substance Registry System: N2-Isobutyryl-2'-Fluoro-2'-deoxyguanosine(80681-25-0)

Safety Data

• Hazardous Substances Data: 80681-25-0(Hazardous Substances Data)

Usage

General Description

N2-Isobutyryl-2'-Fluoro-2'-deoxyguanosine is a chemical compound that belongs to the class of nucleoside analogs. It is a modified form of deoxyguanosine, a building block of DNA. N2-Isobutyryl-2'-Fluoro-2'-deoxyguanosine contains a fluoro group at the 2' carbon position of the deoxyribose sugar and an isobutyryl group attached to the nitrogen atom at the 2 position of the guanine base. N2-Isobutyryl-2'-Fluoro-2'-deoxyguanosine has been studied for its potential antiviral and antitumor properties, as well as its use in chemical biology and drug development. Its modified structure may confer altered or improved biological activities compared to the unmodified nucleoside.

Upstream product

• 78842-12-3 N²-isobutyryl-3'-O,5'-O-bis(tetrahydrofuranyl)-2'-deoxy-2'-fluoroguanosine 
• 146954-69-0 N²-isobutyryl-9-(2-fluoro-3,5-di-O-tetrahydropyran-2-yl-β-D-arabinofuranosyl)guanine 
• 38819-10-2 9-β-D-arabinofuranosylguanine 
• 24880-52-2 2,6-diamino-9-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)purine 
• 146954-68-9 N²-isobutyryl-9-(3,5-di-O-tetrahydropyran-2-yl-β-D-arabinofuranosyl)guanine 
• 200404-37-1 Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl ester 
• 199601-35-9 N-[9-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-isobutyramide 
• 160684-49-1 Acetic acid (2R,3S,4R,5R)-4-hydroxy-5-hydroxymethyl-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 160684-47-9 N2-isobutyryl-9-[3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]guanine 
• 160684-48-0 Acetic acid (2R,3S,3aR,9aR)-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester 
• 34079-68-0 2,6-diamino-9-(β-D-arabinofuranosyl)-purine 
• 69304-44-5 3',5'-O-1,1,3,3-tetraisopropyldisiloxan-1,3-diyl-guanosine 
• 129835-15-0 2-amino-9-((6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-1H-purin-6(9H)-one 
• 146954-66-7 N²-isobutyryl-9-(2-O-isobutyryl-β-D-arabinofuranosyl)guanine 

Downstream Products

• 80681-26-1 N²-isobutyryl-5'-O-monomethoxytrityl-2'-deoxy-2'-fluoroguanosine 
• 78842-13-4 2'-deoxy-2'-fluoroguanosine 
• 144089-96-3 N-(9-((2R,3R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide 

Relevant articles and documents

2′-Fluoro-c-di-GMP as an oral vaccine adjuvant

Bis-(3′-5′)-cyclic dimeric 2′-deoxy-2′-fluoroguanosine monophosphate (2′-F-c-di-GMP) was synthesized through the modified H-phosphonate chemistry. Oral immunization of C57BL/6 mice with Helicobacter pylori cell-free sonicate extract adjuvanted with 2′-F-c

Uniformly modified 2'-deoxy-2'-fluoro phosphorothioate oligonucleotides as nuclease-resistant antisense compounds with high affinity and specificity for RNA targets

'Uniformly' modified phosphodiester or phosphorothioate oligonucleotides incorporating 2'-deoxy-2'-fluoroadenosine, -guanosine, -uridine, and - cytidine, reported herein for the first time, when hybridized with RNA afforded consistent additive enhancement of duplex stability without compromising base-pair specificity. CD spectra of the 2'-deoxy-2'-fluoro- modified oligonucleotides hybridized with RNA indicated that the duplex adopts a fully A-form conformation. The 2'-deoxy-2'-fluoro-modified oligonucleotides in phosphodiester form were not resistant to nucleases; however, the modified phosphorothioate oligonucleotides were highly nuclease resistant and retained exceptional binding affinity to the RNA targets. The stabilizing effects of the 2'-deoxy-2'-fluoro modifications on RNA-DNA duplexes were shown to be superior to those of the 2'-O-methylribo substitutions. RNA hybrid duplexes with uniformly 2'-deoxy-2'-fluoro-modified oligonucleotides did not support HeLa RNase H activity; however, incorporation of the modifications into 'chimeric' oligonucleotides has been shown to activate mammalian RNase H. 'Uniformly' modified 2'-deoxy-2'-fluoro phosphorothioate oligonucleotides afforded antisense molecules with (1) high binding affinity and selectivity for the RNA target and (2) stability toward nucleases.