Home Other Building Blocks 108-53-2
108-53-2,MFCD30183437
Catalog No.:AA003R0Z

108-53-2 | Isocytosine

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1g
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$8.00   $6.00
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5g
97%
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$18.00   $13.00
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10g
97%
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$27.00   $19.00
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25g
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$36.00   $26.00
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA003R0Z
Chemical Name:
Isocytosine
CAS Number:
108-53-2
Molecular Formula:
C4H5N3O
Molecular Weight:
111.1020
MDL Number:
MFCD30183437
SMILES:
Nc1nc(=O)cc[nH]1
NSC Number:
49118
Properties
Properties
 
BP:
252.7 °C at 760 mmHg  
Form:
Solid  
MP:
275 °C  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
170  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
8  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
XLogP3:
-1  

Upstream Synthesis Route

[1]Patent:WO2009/158011,2009,A1,.Locationinpatent:Page/Pagecolumn31

[2]Tetrahedron,2010,vol.66,#6,p.1280-1288

[1]EuropeanJournalofMedicinalChemistry,2012,vol.50,p.18-26

[1]JournalofOrganicChemistry,2011,vol.76,#10,p.4149-4153

[2]JournalofMedicinalChemistry,2006,vol.49,#14,p.4409-4424

[1]JournaloftheAmericanChemicalSociety,2008,vol.130,#46,p.15512-15518

[1]JournaloftheAmericanChemicalSociety,2008,vol.130,#46,p.15512-15518

Downstream Synthesis Route

[1]ChemischeBerichte,1903,vol.36,p.3383

[1]JournaloftheAmericanChemicalSociety,1935,vol.57,p.552

108-53-2   
2-amino-4-bromopyrimidine 

[1]Patent:CN106632077,2017,A.Locationinpatent:Paragraph0040;0041;0042;0043;0044

[2]JournalofOrganicChemistry,1947,vol.12,p.293

[1]Synthesis,2012,vol.44,p.3496-3504

[2]AmericanChemicalJournal,1903,vol.29,p.496    AmericanChemicalJournal,1904,vol.31,p.596

[1]AngewandteChemie-InternationalEdition,2007,vol.46,p.2478-2484

[2]Chemistry-AnAsianJournal,2011,vol.6,p.1252-1262

[3]AmericanChemicalJournal,1905,vol.34,p.564

[4]Patent:US2012/214762,2012,A1.Locationinpatent:Page/Pagecolumn80

Literature

Title: Isocytosine-based inhibitors of xanthine oxidase: design, synthesis, SAR, PK and in vivo efficacy in rat model of hyperuricemia.

Journal: Bioorganic & medicinal chemistry letters 20121215

Title: Understanding the role of base stacking in nucleic acids. MD and QM analysis of tandem GA base pairs in RNA duplexes.

Journal: Physical chemistry chemical physics : PCCP 20120928

Title: Identification of novel isocytosine derivatives as xanthine oxidase inhibitors from a set of virtual screening hits.

Journal: Bioorganic & medicinal chemistry 20120501

Title: Ditopic triply hydrogen-bonded heterodimers.

Journal: Organic & biomolecular chemistry 20110907

Title: Comprehensive core-level study of the effects of isomerism, halogenation, and methylation on the tautomeric equilibrium of cytosine.

Journal: The journal of physical chemistry. A 20110707

Title: Three-dimensional structure and catalytic mechanism of cytosine deaminase.

Journal: Biochemistry 20110607

Title: The role of the formamide/zirconia system in the synthesis of nucleobases and biogenic carboxylic acid derivatives.

Journal: Journal of molecular evolution 20100801

Title: Design and synthesis of novel SATE derivatives of acyclic isocytosine and 9-deazaadenine C-nucleosides.

Journal: Nucleosides, nucleotides & nucleic acids 20100301

Title: Incorporation of non-natural nucleotides into template-switching oligonucleotides reduces background and improves cDNA synthesis from very small RNA samples.

Journal: BMC genomics 20100101

Title: Error-Prone Translesion DNA Synthesis by Escherichia coli DNA Polymerase IV (DinB) on Templates Containing 1,2-dihydro-2-oxoadenine.

Journal: Journal of nucleic acids 20100101

Title: Synthesis and degradation of nucleic acid components by formamide and iron sulfur minerals.

Journal: Journal of the American Chemical Society 20081119

Title: Comparison of different real-time PCR chemistries and their suitability for detection and quantification of genetically modified organisms.

Journal: BMC biotechnology 20080101

Title: Discovery of a novel warhead against beta-secretase through fragment-based lead generation.

Journal: Journal of medicinal chemistry 20071129

Title: Application of fragment-based lead generation to the discovery of novel, cyclic amidine beta-secretase inhibitors with nanomolar potency, cellular activity, and high ligand efficiency.

Journal: Journal of medicinal chemistry 20071129

Title: Theoretical study of the intermolecular H-bonding and intermolecular proton transfer between isocytosine tautomeric forms and R,S-lactic acid.

Journal: Journal of molecular modeling 20070101

Title: Isocytosine as a hydrogen-bonding partner and as a ligand in metal complexes.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20051104

Title: Parallel DNA double helices incorporating isoG or m5isoC bases studied by FTIR, CD and molecular modeling.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20050201

Title: Biochemical characterization of rat intestine development using high-resolution magic-angle-spinning 1H NMR spectroscopy and multivariate data analysis.

Journal: Journal of proteome research 20050101

Title: Complex formation of isocytosine tautomers with PdII and PtII.

Journal: Inorganic chemistry 20040531

Title: Systematic quantum chemical study of DNA-base tautomers.

Journal: Journal of computational chemistry 20040115

Title: Synthesis and properties of oligonucleotides containing C-2 and/or C-5 substituted arabinofuranosyluracils.

Journal: Nucleic acids research. Supplement (2001) 20030101

Title: Specific interaction of isocytosine and amino acid carboxylic group shifts the base tautomeric equilibrium.

Journal: Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20030101

Title: Chemical stability of 2'-deoxy-5-methylisocytidine during oligodeoxynucleotide synthesis and deprotection.

Journal: Nucleosides, nucleotides & nucleic acids 20020101

Title: Probing structure and function with alternative nucleic acids bearing 2',5'-linked, zwitterionic, and isocytosine-isoguanine components.

Journal: Methods (San Diego, Calif.) 20010201

Title: Terpsichorean movements of pentaammineruthenium on pyrimidine and isocytosine ligands.

Journal: Inorganic chemistry 20010129

Title: Selective hydrolysis of 2,4-diaminopyrimidine systems: a theoretical and experimental insight into an old rule.

Journal: The Journal of organic chemistry 20010112

Title: Quantum chemistry predicted correlations between geometric isomerism (conformation) of -OH and =NH substituents and typical group frequencies of nucleic acid bases: cytosine.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20010101

Title: Inhibition of sandfly fever Sicilian virus (Phlebovirus) replication in vitro by antiviral compounds.

Journal: Research in virology 19970101

Title: Fine structural specificity differences of trimethoprim allergenic determinants.

Journal: Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology 19961001

Title: Structure-activity relationships for the binding of ligands to xanthine or guanine phosphoribosyl-transferase from Toxoplasma gondii.

Journal: Biochemical pharmacology 19951109

Title: Structure-activity relationship of ligands of uracil phosphoribosyltransferase from Toxoplasma gondii.

Journal: Biochemical pharmacology 19940817

Title: Antiviral and other bioactivities of pyrimidinones.

Journal: Pharmacology & therapeutics 19850101

Title: "Isocytosine". Molecule of the Week. American Chemical Society. Retrieved November 1, 2012.

Title: Hoshika S, et al. Hachimoji DNA and RNA: A genetic system with eight building blocks. Science. 2019 Feb 22;363(6429):884-887.

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