108-53-2,MFCD30183437
Catalog No.:AA003R0Z

108-53-2 | Isocytosine

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1g
97%
in stock  
$8.00   $6.00
- +
5g
97%
in stock  
$19.00   $13.00
- +
10g
97%
in stock  
$28.00   $19.00
- +
25g
≥98%
in stock  
$43.00   $30.00
- +
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
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  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
8  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0  
Rotatable Bond Count:
0  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
-1  

Synonyms
 
  
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.

Quotation Request
Company Name:
*
Contact Person:
*
Email:
*
Quantity Required:
*
Country:
Additional Info:
SDS
Historical Records
Tags:108-53-2 Molecular Formula|108-53-2 MDL|108-53-2 SMILES|108-53-2 Isocytosine
Catalog No.: AA003R0Z
108-53-2,MFCD30183437
108-53-2 | Isocytosine
Pack Size: 1g
Purity: 97%
in stock
$8.00 $6.00
Pack Size: 5g
Purity: 97%
in stock
$19.00 $13.00
Pack Size: 10g
Purity: 97%
in stock
$28.00 $19.00
Pack Size: 25g
Purity: ≥98%
in stock
$43.00 $30.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
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
BP: 252.7 °C at 760 mmHg  
Form: Solid  
MP: 275 °C  
Storage: Inert atmosphere;Room Temperature;  
Complexity: 170  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 8  
Hydrogen Bond Acceptor Count: 2  
Hydrogen Bond Donor Count: 2  
Isotope Atom Count: 0  
Rotatable Bond Count: 0  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: -1  
124:   
Upstream Synthesis Route
108-53-2    3993-78-0 

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

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

108-53-2    3993-78-0 

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

108-53-2    3993-78-0 

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

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

77287-34-4    557-01-7    151-51-9    108-53-2    144-62-7 

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

77287-34-4    557-01-7    151-51-9    108-53-2    120-73-0    66224-66-6 

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

Downstream Synthesis Route
155-90-8    108-53-2 

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

25957-58-8    108-53-2 

[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

108-53-2    61937-71-1 

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

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

108-53-2    7254-29-7 

[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 fold

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

Journal: Bioorganic & medicinal chemistry letters20121215

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 : PCCP20120928

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

Journal: Bioorganic & medicinal chemistry20120501

Title: Ditopic triply hydrogen-bonded heterodimers.

Journal: Organic & biomolecular chemistry20110907

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. A20110707

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

Journal: Biochemistry20110607

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

Journal: Journal of molecular evolution20100801

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

Journal: Nucleosides, nucleotides & nucleic acids20100301

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

Journal: BMC genomics20100101

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 acids20100101

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

Journal: Journal of the American Chemical Society20081119

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

Journal: BMC biotechnology20080101

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

Journal: Journal of medicinal chemistry20071129

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 chemistry20071129

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 modeling20070101

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 spectroscopy20050201

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

Journal: Journal of proteome research20050101

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

Journal: Inorganic chemistry20040531

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

Journal: Journal of computational chemistry20040115

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 acids20020101

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 chemistry20010129

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

Journal: The Journal of organic chemistry20010112

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 spectroscopy20010101

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

Journal: Research in virology19970101

Title: Fine structural specificity differences of trimethoprim allergenic determinants.

Journal: Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology19961001

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

Journal: Biochemical pharmacology19951109

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

Journal: Biochemical pharmacology19940817

Title: Antiviral and other bioactivities of pyrimidinones.

Journal: Pharmacology & therapeutics19850101

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.

Building Blocks More >
59227-89-3
59227-89-3
Laurocapram
AA003R5L | MFCD00190580
7662-51-3
7662-51-3
L-Tyrosine hydrazide
AA003RAU | MFCD00007609
272792-14-0
272792-14-0
Methyl (4-cyanophenoxy)acetate
AA003RFU | MFCD05855148
2719-08-6
2719-08-6
Methyl 2-acetamidobenzoate
AA003RJF | MFCD00144760
84199-98-4
84199-98-4
Methyl 3-(3-pyridyl)propionate
AA003RMN | MFCD01075660
41221-47-0
41221-47-0
Methyl 3-isocyanatobenzoate
AA003RPV | MFCD00037077
517870-23-4
517870-23-4
Methyl 5-(2-thienyl)isoxazole-3-carboxylate
AA003RTM | MFCD03778976
683-98-7
683-98-7
Methyl bromodifluoroacetate
AA003RWX | MFCD06248118
624-24-8
624-24-8
METHYL VALERATE
AA003S08 | MFCD00009478
69159-49-5
69159-49-5
1-Benzhydryl-n-methylazetidin-3-amine
AA003S4I | MFCD01665356
Submit
© 2017 AA BLOCKS, INC. All rights reserved.