2497-02-1,MFCD00005206
Catalog No.:AA00I4P0

2497-02-1 | (2S)-2-acetamido-3-(1H-imidazol-4-yl)propanoic acid

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Purity
Availability
Price(USD)
Quantity
  
5mg
2 weeks  
$863.00   $604.00
- +
500mg
2 weeks  
$1,029.00   $720.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA00I4P0
Chemical Name:
(2S)-2-acetamido-3-(1H-imidazol-4-yl)propanoic acid
CAS Number:
2497-02-1
Molecular Formula:
C7H13NO3
Molecular Weight:
159.1830
MDL Number:
MFCD00005206
SMILES:
CC(=O)NC(C(=O)O)C(C)C
Properties
Computed Properties
 
Complexity:
232  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
14  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0  
Rotatable Bond Count:
4  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
-0.7  

Downstream Synthesis Route

[1]JournaloftheAmericanChemicalSociety,1959,vol.81,p.2208,2213

[1]Cerezo,Vanessa;Afonso,Ana;Planas,Marta;Feliu,Lidia[Tetrahedron,2007,vol.63,#42,p.10445-10453]

[2]Schädel,Nicole;Icik,Esra;Martini,Maike;Altevogt,Luca;Ramming,Isabell;Greulich,Andreas;Baro,Angelika;Bilitewski,Ursula;Laschat,Sabine[Synthesis,2021,vol.53,#13,p.2260-2268]

[3]Giralt,Ernest;Viladrich,Roser;Pedroso,Enrique[OrganicMagneticResonance,1983,vol.21,#3,p.208-213]

[4]Goto,Koichi;Yano,Yoshihiro;Okada,Eiji;Liu,Chin-Wen;Yamamoto,Kiyoto;Ueoka,Ryuichi[JournalofOrganicChemistry,2003,vol.68,#3,p.865-870]

[5]Goto,Koichi;Yano,Yoshihiro;Okada,Eiji;Liu,Chin-Wen;Yamamoto,Kiyoto;Ueoka,Ryuichi[JournalofOrganicChemistry,2003,vol.68,#3,p.865-870]

2494-12-4    2497-02-1   
Nα-Acetyl-Nτ-<1-(3,4-dihydroxyphenyl)-2-N-acetylamino-ethyl>-histidine 

[1]Andersen,SvendOlav;Jacobsen,JensPeter;Roepstorff,Peter;Peter,MartinG.[TetrahedronLetters,1991,vol.32,#34,p.4287-4290]

[1]Patent:US2014/127138,2014,A1.Locationinpatent:Paragraph0323;0324

[2]OrganicLetters,2006,vol.8,p.3215-3217

[1]Siopa,Filipa;Pereira,AliceS.;Ferreira,LuisaM.;MatildeMarques;Branco,PaulaS.[BioorganicChemistry,2012,vol.44,p.19-24]

Literature

Title: Synthesis of catecholamine conjugates with nitrogen-centered bionucleophiles.

Journal: Bioorganic chemistry 20121001

Title: Reduction of chronic graft injury with a new HTK-based preservation solution in a murine heart transplantation model.

Journal: Cryobiology 20120601

Title: Effects of chronic and periodic exposures to ammonia on the eye health in juvenile Atlantic halibut (Hippoglossus hippoglossus).

Journal: Fish physiology and biochemistry 20120401

Title: Susceptibility of Atlantic salmon lenses to hydrogen peroxide oxidation ex vivo after being fed diets with vegetable oil and methylmercury.

Journal: Experimental eye research 20110501

Title: Tumor targeting efficiency of bare nanoparticles does not mean the efficacy of loaded anticancer drugs: importance of radionuclide imaging for optimization of highly selective tumor targeting polymeric nanoparticles with or without drug.

Journal: Journal of controlled release : official journal of the Controlled Release Society 20101015

Title: N-acetylhistidine, a novel osmolyte in the lens of Atlantic salmon (Salmo salar L.).

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20101001

Title: Ability of hypochlorous acid and N-chloramines to chlorinate DNA and its constituents.

Journal: Chemical research in toxicology 20100719

Title: Influence of histidine on the release of all-trans retinoic acid from self-assembled glycol chitosan nanoparticles.

Journal: Drug development and industrial pharmacy 20100701

Title: Effect of plant-based feed ingredients on osmoregulation in the Atlantic salmon lens.

Journal: Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology 20100401

Title: Prostate cancer-targeted imaging using magnetofluorescent polymeric nanoparticles functionalized with bombesin.

Journal: Pharmaceutical research 20100401

Title: Neuropharmacology of vestibular system disorders.

Journal: Current neuropharmacology 20100301

Title: Deferoxamine, the newly developed iron chelator LK-614 and N-alpha-acetyl-histidine in myocardial protection.

Journal: Interactive cardiovascular and thoracic surgery 20100201

Title: Occurrence of a novel acetylated amino acid, N(alpha)-acetylhistidine, in skeletal muscle of freshwater fish and other ectothermic vertebrates.

Journal: Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology 20090301

Title: The melatonin metabolite N-acetyl-5-methoxykynuramine is a potent singlet oxygen scavenger.

Journal: Journal of pineal research 20090101

Title: Solution interactions between the uranyl cation [UO2(2+)] and histidine, N-acetyl-histidine, tyrosine, and N-acetyl-tyrosine.

Journal: Journal of inorganic biochemistry 20090101

Title: Genome-wide transcription analysis of histidine-related cataract in Atlantic salmon (Salmo salar L).

Journal: Molecular vision 20090101

Title: Myocardial protection with the use of L-arginine and N-alpha-acetyl-histidine.

Journal: Transplantation proceedings 20090101

Title: Identification of plasma proteins that are susceptible to thiol oxidation by hypochlorous acid and N-chloramines.

Journal: Chemical research in toxicology 20080901

Title: Low-density lipoprotein has an enormous capacity to bind (E)-4-hydroxynon-2-enal (HNE): detection and characterization of lysyl and histidyl adducts containing multiple molecules of HNE.

Journal: Chemical research in toxicology 20080721

Title: Attenuated cold storage injury of rat livers using a modified HTK solution.

Journal: The Journal of surgical research 20080501

Title: Improvement of the cold storage of blood vessels with a vascular preservation solution. Study in porcine aortic segments.

Journal: Journal of vascular surgery 20080201

Title: Endothelial dysfunction after long-term cold storage in HTK organ preservation solutions: effects of iron chelators and N-alpha-acetyl-L-histidine.

Journal: The Journal of heart and lung transplantation : the official publication of the International Society for Heart Transplantation 20080201

Title: Efficient preparation of xanthine-containing oligodeoxynucleotide from oxanine-containing oligodeoxynucleotide, catalyzed by N alpha-acetyl-L-histidine.

Journal: Nucleic acids symposium series (2004) 20080101

Title: Magnetic assembly and patterning of vesicle/nanoparticle aggregates.

Journal: Journal of the American Chemical Society 20071010

Title: pH-tunable equilibria in azocrown ethers with histidine moieties.

Journal: Bioelectrochemistry (Amsterdam, Netherlands) 20070901

Title: Detection of kynurenine modifications in proteins using a monoclonal antibody.

Journal: Journal of immunological methods 20070731

Title: Possible bioactivation pathways of lamotrigine.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20070701

Title: Histidine-induced injury to cultured liver cells, effects of histidine derivatives and of iron chelators.

Journal: Cellular and molecular life sciences : CMLS 20070101

Title: N-acetyl histidine-conjugated glycol chitosan self-assembled nanoparticles for intracytoplasmic delivery of drugs: endocytosis, exocytosis and drug release.

Journal: Journal of controlled release : official journal of the Controlled Release Society 20060928

Title: Purification and sequence identification of anserinase.

Journal: The FEBS journal 20051201

Title: Purification and characterization of a novel aminoacylase from Streptomyces mobaraensis.

Journal: Bioscience, biotechnology, and biochemistry 20051001

Title: 3-hydroxykynurenine-mediated modification of human lens proteins: structure determination of a major modification using a monoclonal antibody.

Journal: The Journal of biological chemistry 20050610

Title: Histidine nutrition and genotype affect cataract development in Atlantic salmon, Salmo salar L.

Journal: Journal of fish diseases 20050601

Title: Kinetic analysis of the role of histidine chloramines in hypochlorous acid mediated protein oxidation.

Journal: Biochemistry 20050517

Title: Model studies on protein side chain modification by 4-oxo-2-nonenal.

Journal: Chemical research in toxicology 20030401

Title: Structural basis of protein-bound endogenous aldehydes. Chemical and immunochemical characterizations of configurational isomers of a 4-hydroxy-2-nonenal-histidine adduct.

Journal: The Journal of biological chemistry 20030214

Title: Ultraviolet spectrophotometric characterization of copper(II) complexes with imidazole N-methyl derivatives of L-histidine in aqueous solution.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20030101

Title: Mechanisms of reactions of flavin mononucleotide triplet with aromatic amino acids.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20020701

Title: Interaction of copper(II) with imidazole pyridine nitrogen-containing ligands in aqueous medium: a spectroscopic study.

Journal: Journal of inorganic biochemistry 20020101

Title: Differential expression of carnosine, homocarnosine and N-acetyl-L-histidine hydrolytic activities in cultured rat macroglial cells.

Journal: Journal of molecular neuroscience : MN 20011201

Title: Characterization of sterically stabilized cisplatin liposomes by nuclear magnetic resonance.

Journal: Biochimica et biophysica acta 20010209

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SDS
Tags:2497-02-1 Molecular Formula|2497-02-1 MDL|2497-02-1 SMILES|2497-02-1 (2S)-2-acetamido-3-(1H-imidazol-4-yl)propanoic acid
Catalog No.: AA00I4P0
2497-02-1,MFCD00005206
2497-02-1 | (2S)-2-acetamido-3-(1H-imidazol-4-yl)propanoic acid
Pack Size: 5mg
Purity:
2 weeks
$863.00 $604.00
Pack Size: 500mg
Purity:
2 weeks
$1,029.00 $720.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA00I4P0
Chemical Name: (2S)-2-acetamido-3-(1H-imidazol-4-yl)propanoic acid
CAS Number: 2497-02-1
Molecular Formula: C7H13NO3
Molecular Weight: 159.1830
MDL Number: MFCD00005206
SMILES: CC(=O)NC(C(=O)O)C(C)C
Properties
Complexity: 232  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 1  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 14  
Hydrogen Bond Acceptor Count: 4  
Hydrogen Bond Donor Count: 3  
Isotope Atom Count: 0  
Rotatable Bond Count: 4  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: -0.7  
Downstream Synthesis Route
2497-02-1    6367-11-9 

[1]JournaloftheAmericanChemicalSociety,1959,vol.81,p.2208,2213

67-56-1    2497-02-1    36097-48-0 

[1]Cerezo,Vanessa;Afonso,Ana;Planas,Marta;Feliu,Lidia[Tetrahedron,2007,vol.63,#42,p.10445-10453]

[2]Schädel,Nicole;Icik,Esra;Martini,Maike;Altevogt,Luca;Ramming,Isabell;Greulich,Andreas;Baro,Angelika;Bilitewski,Ursula;Laschat,Sabine[Synthesis,2021,vol.53,#13,p.2260-2268]

[3]Giralt,Ernest;Viladrich,Roser;Pedroso,Enrique[OrganicMagneticResonance,1983,vol.21,#3,p.208-213]

[4]Goto,Koichi;Yano,Yoshihiro;Okada,Eiji;Liu,Chin-Wen;Yamamoto,Kiyoto;Ueoka,Ryuichi[JournalofOrganicChemistry,2003,vol.68,#3,p.865-870]

[5]Goto,Koichi;Yano,Yoshihiro;Okada,Eiji;Liu,Chin-Wen;Yamamoto,Kiyoto;Ueoka,Ryuichi[JournalofOrganicChemistry,2003,vol.68,#3,p.865-870]

2494-12-4    2497-02-1   
Nα-Acetyl-Nτ-<1-(3,4-dihydroxyphenyl)-2-N-acetylamino-ethyl>-histidine 

[1]Andersen,SvendOlav;Jacobsen,JensPeter;Roepstorff,Peter;Peter,MartinG.[TetrahedronLetters,1991,vol.32,#34,p.4287-4290]

108-24-7    645-35-2    2497-02-1 

[1]Patent:US2014/127138,2014,A1.Locationinpatent:Paragraph0323;0324

[2]OrganicLetters,2006,vol.8,p.3215-3217

2494-12-4    2497-02-1    176226-41-8    145873-65-0 

[1]Siopa,Filipa;Pereira,AliceS.;Ferreira,LuisaM.;MatildeMarques;Branco,PaulaS.[BioorganicChemistry,2012,vol.44,p.19-24]

Literature fold

Title: Synthesis of catecholamine conjugates with nitrogen-centered bionucleophiles.

Journal: Bioorganic chemistry20121001

Title: Reduction of chronic graft injury with a new HTK-based preservation solution in a murine heart transplantation model.

Journal: Cryobiology20120601

Title: Effects of chronic and periodic exposures to ammonia on the eye health in juvenile Atlantic halibut (Hippoglossus hippoglossus).

Journal: Fish physiology and biochemistry20120401

Title: Susceptibility of Atlantic salmon lenses to hydrogen peroxide oxidation ex vivo after being fed diets with vegetable oil and methylmercury.

Journal: Experimental eye research20110501

Title: Tumor targeting efficiency of bare nanoparticles does not mean the efficacy of loaded anticancer drugs: importance of radionuclide imaging for optimization of highly selective tumor targeting polymeric nanoparticles with or without drug.

Journal: Journal of controlled release : official journal of the Controlled Release Society20101015

Title: N-acetylhistidine, a novel osmolyte in the lens of Atlantic salmon (Salmo salar L.).

Journal: American journal of physiology. Regulatory, integrative and comparative physiology20101001

Title: Ability of hypochlorous acid and N-chloramines to chlorinate DNA and its constituents.

Journal: Chemical research in toxicology20100719

Title: Influence of histidine on the release of all-trans retinoic acid from self-assembled glycol chitosan nanoparticles.

Journal: Drug development and industrial pharmacy20100701

Title: Effect of plant-based feed ingredients on osmoregulation in the Atlantic salmon lens.

Journal: Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology20100401

Title: Prostate cancer-targeted imaging using magnetofluorescent polymeric nanoparticles functionalized with bombesin.

Journal: Pharmaceutical research20100401

Title: Neuropharmacology of vestibular system disorders.

Journal: Current neuropharmacology20100301

Title: Deferoxamine, the newly developed iron chelator LK-614 and N-alpha-acetyl-histidine in myocardial protection.

Journal: Interactive cardiovascular and thoracic surgery20100201

Title: Occurrence of a novel acetylated amino acid, N(alpha)-acetylhistidine, in skeletal muscle of freshwater fish and other ectothermic vertebrates.

Journal: Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology20090301

Title: The melatonin metabolite N-acetyl-5-methoxykynuramine is a potent singlet oxygen scavenger.

Journal: Journal of pineal research20090101

Title: Solution interactions between the uranyl cation [UO2(2+)] and histidine, N-acetyl-histidine, tyrosine, and N-acetyl-tyrosine.

Journal: Journal of inorganic biochemistry20090101

Title: Genome-wide transcription analysis of histidine-related cataract in Atlantic salmon (Salmo salar L).

Journal: Molecular vision20090101

Title: Myocardial protection with the use of L-arginine and N-alpha-acetyl-histidine.

Journal: Transplantation proceedings20090101

Title: Identification of plasma proteins that are susceptible to thiol oxidation by hypochlorous acid and N-chloramines.

Journal: Chemical research in toxicology20080901

Title: Low-density lipoprotein has an enormous capacity to bind (E)-4-hydroxynon-2-enal (HNE): detection and characterization of lysyl and histidyl adducts containing multiple molecules of HNE.

Journal: Chemical research in toxicology20080721

Title: Attenuated cold storage injury of rat livers using a modified HTK solution.

Journal: The Journal of surgical research20080501

Title: Improvement of the cold storage of blood vessels with a vascular preservation solution. Study in porcine aortic segments.

Journal: Journal of vascular surgery20080201

Title: Endothelial dysfunction after long-term cold storage in HTK organ preservation solutions: effects of iron chelators and N-alpha-acetyl-L-histidine.

Journal: The Journal of heart and lung transplantation : the official publication of the International Society for Heart Transplantation20080201

Title: Efficient preparation of xanthine-containing oligodeoxynucleotide from oxanine-containing oligodeoxynucleotide, catalyzed by N alpha-acetyl-L-histidine.

Journal: Nucleic acids symposium series (2004)20080101

Title: Magnetic assembly and patterning of vesicle/nanoparticle aggregates.

Journal: Journal of the American Chemical Society20071010

Title: pH-tunable equilibria in azocrown ethers with histidine moieties.

Journal: Bioelectrochemistry (Amsterdam, Netherlands)20070901

Title: Detection of kynurenine modifications in proteins using a monoclonal antibody.

Journal: Journal of immunological methods20070731

Title: Possible bioactivation pathways of lamotrigine.

Journal: Drug metabolism and disposition: the biological fate of chemicals20070701

Title: Histidine-induced injury to cultured liver cells, effects of histidine derivatives and of iron chelators.

Journal: Cellular and molecular life sciences : CMLS20070101

Title: N-acetyl histidine-conjugated glycol chitosan self-assembled nanoparticles for intracytoplasmic delivery of drugs: endocytosis, exocytosis and drug release.

Journal: Journal of controlled release : official journal of the Controlled Release Society20060928

Title: Purification and sequence identification of anserinase.

Journal: The FEBS journal20051201

Title: Purification and characterization of a novel aminoacylase from Streptomyces mobaraensis.

Journal: Bioscience, biotechnology, and biochemistry20051001

Title: 3-hydroxykynurenine-mediated modification of human lens proteins: structure determination of a major modification using a monoclonal antibody.

Journal: The Journal of biological chemistry20050610

Title: Histidine nutrition and genotype affect cataract development in Atlantic salmon, Salmo salar L.

Journal: Journal of fish diseases20050601

Title: Kinetic analysis of the role of histidine chloramines in hypochlorous acid mediated protein oxidation.

Journal: Biochemistry20050517

Title: Model studies on protein side chain modification by 4-oxo-2-nonenal.

Journal: Chemical research in toxicology20030401

Title: Structural basis of protein-bound endogenous aldehydes. Chemical and immunochemical characterizations of configurational isomers of a 4-hydroxy-2-nonenal-histidine adduct.

Journal: The Journal of biological chemistry20030214

Title: Ultraviolet spectrophotometric characterization of copper(II) complexes with imidazole N-methyl derivatives of L-histidine in aqueous solution.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy20030101

Title: Mechanisms of reactions of flavin mononucleotide triplet with aromatic amino acids.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy20020701

Title: Interaction of copper(II) with imidazole pyridine nitrogen-containing ligands in aqueous medium: a spectroscopic study.

Journal: Journal of inorganic biochemistry20020101

Title: Differential expression of carnosine, homocarnosine and N-acetyl-L-histidine hydrolytic activities in cultured rat macroglial cells.

Journal: Journal of molecular neuroscience : MN20011201

Title: Characterization of sterically stabilized cisplatin liposomes by nuclear magnetic resonance.

Journal: Biochimica et biophysica acta20010209

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