Home Amines 58970-76-6
58970-76-6,MFCD00083262
Catalog No.:AA0036XY

58970-76-6 | (2S)-2-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido]-4-methylpentanoic acid

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10mg
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50mg
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100mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0036XY
Chemical Name:
(2S)-2-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido]-4-methylpentanoic acid
CAS Number:
58970-76-6
Molecular Formula:
C16H24N2O4
Molecular Weight:
308.3728
MDL Number:
MFCD00083262
SMILES:
O[C@H](C(=O)N[C@H](C(=O)O)CC(C)C)[C@@H](Cc1ccccc1)N
Properties
Properties
 
BP:
604.7°C at 760 mmHg  
Form:
Solid  
MP:
245 °C (dec.)(lit.)  
Refractive Index:
1.5800 (estimate)  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
367  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
8  
XLogP3:
-1  

Downstream Synthesis Route

[1]Takita,T.etal.[JournalofMedicinalChemistry,1977,vol.20,p.510-515]

[2]Kobayashi,Susumu;Isobe,Toshiyuki;Ohno,Masaji[TetrahedronLetters,1984,vol.25,#44,p.5079-5082]

[3]CurrentPatentAssignee:MICROBIALCHEMISTRYRESEARCHFOUNDATION;ZHBISEIBUTSUKAGAKUKENKYUKAI-FR2318863,1977,B1[Chem.Abstr.,1977,vol.87,#23736][Chem.Abstr.,1977,vol.87,#23736]

58970-76-6   
CASUnavailable 

[1]Takita,T.etal.[JournalofMedicinalChemistry,1977,vol.20,p.510-515]

[2]CurrentPatentAssignee:MICROBIALCHEMISTRYRESEARCHFOUNDATION;ZHBISEIBUTSUKAGAKUKENKYUKAI-FR2318863,1977,B1[Chem.Abstr.,1977,vol.87,#23736][Chem.Abstr.,1977,vol.87,#23736]

[1]Pearson;Hines[JournalofOrganicChemistry,1989,vol.54,#17,p.4235-4237]

[2]Koseki,Koshi;Ebata,Takashi;Matsushita,Hajime[Bioscience,BiotechnologyandBiochemistry,1996,vol.60,#3,p.534-536]

[1]Wasserman,HarryH.;Xia,Mingde;Petersen,AndersK.;Jorgensen,MichaelR.;Curtis,ErinA.[TetrahedronLetters,1999,vol.40,#34,p.6163-6166]

[1]Semple,J.Edward;Owens,TimothyD.;Nguyen,Khanh;Levy,OdileE.[OrganicLetters,2000,vol.2,#18,p.2769-2772]

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Journal: Cancer letters 20041208

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Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20040901

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Journal: Journal of hypertension 20040101

Title: [Leu-enkephalin homogeneously labeled with tritium in studying the Selank inhibiting effect on the enkephalin-degrading enzymes of human plasma].

Journal: Bioorganicheskaia khimiia 20040101

Title: Aminopeptidase inhibitor bestatin stimulates microvascular endothelial cell invasion in a fibrin matrix.

Journal: Thrombosis and haemostasis 20031101

Title: Aminopeptidase inhibitors inhibit proliferation and induce apoptosis of K562 and STI571-resistant K562 cell lines through the MAPK and GSK-3beta pathways.

Journal: Leukemia & lymphoma 20031101

Title: [A case of renal cell carcinoma with lymph node metastasis keeping remission for five years by adjuvant immunotherapy with ubenimex].

Journal: Gan to kagaku ryoho. Cancer & chemotherapy 20031001

Title: Synthesis and biological evaluation of novel flavone-8-acetic acid derivatives as reversible inhibitors of aminopeptidase N/CD13.

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Title: [Chemotherapy with ubenimex corresponding to patient age and organ disorder for 18 cases of acute myelogeneous leukemia in elderly patients--effects, complications and long-term survival].

Journal: Gan to kagaku ryoho. Cancer & chemotherapy 20030801

Title: Irreversible inhibition of CD13/aminopeptidase N by the antiangiogenic agent curcumin.

Journal: Chemistry & biology 20030801

Title: Leukotriene A4 signaling, inflammation, and cancer.

Journal: Journal of the National Cancer Institute 20030716

Title: Leukotriene A4 hydrolase in rat and human esophageal adenocarcinomas and inhibitory effects of bestatin.

Journal: Journal of the National Cancer Institute 20030716

Title: Activity of hydrolytic enzymes in tumour cells is a determinant for anti-tumour efficacy of the melphalan containing prodrug J1.

Journal: Journal of drug targeting 20030701

Title: The most potent organophosphorus inhibitors of leucine aminopeptidase. Structure-based design, chemistry, and activity.

Journal: Journal of medicinal chemistry 20030619

Title: Bestatin selectively suppresses the growth of leukemic stem/progenitor cells with BCR/ABL mRNA transcript in patients with chronic myelogeneous leukemia.

Journal: International immunopharmacology 20030601

Title: Bestatin results in pathophysiological changes similar to preeclampsia in rats via induction of placental apoptosis.

Journal: Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20030601

Title: Aminopeptidase N inhibitors and SARS.

Journal: Lancet (London, England) 20030503

Title: Randomized double-blind placebo-controlled trial of bestatin in patients with resected stage I squamous-cell lung carcinoma.

Journal: Journal of the National Cancer Institute 20030416

Title: A comparative study on the rectal aminopeptidase enzymatic activities of different species.

Journal: Die Pharmazie 20030301

Title: Action of three ectopeptidases on corticotropin-releasing factor: metabolism and functional aspects.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20030101

Title: Enhancement of sensitivity by bestatin of acute promyelocytic leukemia NB4 cells to all-trans retinoic acid.

Journal: Leukemia research 20021201

Title: Induction of graft-versus-host disease and a graft-versus-leukemia effect using ubenimex in a patient with infantile leukemia relapsing after an unrelated cord blood transplant.

Journal: Bone marrow transplantation 20021001

Title: Characterization of aminopeptidase activity from three species of microsporidia: Encephalitozoon cuniculi, Encephalitozoon hellem, and Vittaforma corneae.

Journal: The Journal of parasitology 20021001

Title: Effect of Bacillus anthracis lethal toxin on human peripheral blood mononuclear cells.

Journal: FEBS letters 20020911

Title: CD13/aminopeptidase N-induced lymphocyte involvement in inflamed joints of patients with rheumatoid arthritis.

Journal: Arthritis and rheumatism 20020901

Title: Aminopeptidase inhibitors bestatin and actinonin inhibit cell proliferation of myeloma cells predominantly by intracellular interactions.

Journal: Cancer letters 20020828

Title: Effects of naloxone and post-tetanic stimulation on isolated guinea-pig ileum followed by long exposure to morphine and bestatin.

Journal: The Journal of toxicological sciences 20020801

Title: Cloning and characterization of a leucyl aminopeptidase from three pathogenic Leishmania species.

Journal: The Journal of biological chemistry 20020719

Title: Leukemic cell-surface CD13/aminopeptidase N and resistance to apoptosis mediated by endothelial cells.

Journal: Journal of the National Cancer Institute 20020703

Title: Inhibition of fiber cell globulization and hyperglycemia-induced lens opacification by aminopeptidase inhibitor bestatin.

Journal: Investigative ophthalmology & visual science 20020701

Title: Possible involvement of placental peptidases that degrade gonadotropin-releasing hormone (GnRH) in the dynamic pattern of placental hCG secretion via GnRH degradation.

Journal: Placenta 20020701

Title: Membrane-associated dipeptidyl peptidase IV is involved in encystation-specific gene expression during Giardia differentiation.

Journal: The Biochemical journal 20020615

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: Role of CD13/aminopeptidase N in rat lymphocytic alveolitis caused by thoracic irradiation.

Journal: Radiation research 20020201

Title: Characterization of a cytosolic aminopeptidase from Encephalitozoon intestinalis.

Journal: Parasitology 20020101

Title: Neutral endopeptidase knockout induces hyperalgesia in a model of visceral pain, an effect related to bradykinin and nitric oxide.

Journal: Journal of molecular neuroscience : MN 20020101

Title: Zinc and Manduca sexta hemocyte functions.

Journal: Journal of insect science (Online) 20020101

Title: The neuropeptide FF analogue, 1DMe, acts as a functional opioid autoreceptor antagonist in the rat spinal cord.

Journal: European journal of pharmacology 20011102

Title: Comparison of vaginal aminopeptidase enzymatic activities in various animals and in humans.

Journal: The Journal of pharmacy and pharmacology 20011101

Title: Augmentation of death ligand-induced apoptosis by aminopeptidase inhibitors in human solid tumor cell lines.

Journal: International journal of cancer 20011101

Title: [Effects of ubenimex ( bestatin) on the immunity of patients with squamous cell lung carcinoma treated with chemotherapy].

Journal: Zhongguo fei ai za zhi = Chinese journal of lung cancer 20011020

Title: Major histocompatibility complex class I-presented antigenic peptides are degraded in cytosolic extracts primarily by thimet oligopeptidase.

Journal: The Journal of biological chemistry 20010928

Title: The role of aminopeptidases in haemoglobin degradation in Plasmodium falciparum-infected erythrocytes.

Journal: Molecular and biochemical parasitology 20010928

Title: Studies on the aminopeptidase activities of Porphyromonas gingivalis.

Journal: Oral microbiology and immunology 20010801

Title: [Aminopeptidase inhibitor Bestatin induces HL-60 cell apoptosis through activating caspase 3].

Journal: Zhonghua xue ye xue za zhi = Zhonghua xueyexue zazhi 20010701

Title: Expression of attractin and its differential enzyme activity in glioma cells.

Journal: Biochemical and biophysical research communications 20010608

Title: Effects of dipeptide bestatin on Porphyromonas gingivalis and epithelial cells.

Journal: Journal of periodontology 20010601

Title: Possible involvement of EBV-mediated alpha-fodrin cleavage for organ-specific autoantigen in Sjogren's syndrome.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20010501

Title: Aminopeptidase N regulated by zinc in human prostate participates in tumor cell invasion.

Journal: International journal of cancer 20010401

Title: Different types of antagonism by losartan and irbesartan on the effects of angiotensin II and its degradation products in rabbit arteries.

Journal: Fundamental & clinical pharmacology 20010401

Title: Bestatin as an experimental tool in mammals.

Journal: Current drug metabolism 20010301

Title: Crystal structure of human leukotriene A(4) hydrolase, a bifunctional enzyme in inflammation.

Journal: Nature structural biology 20010201

Title: Characterization of the pro-aminopeptidase from Aeromonas caviae T-64.

Journal: Bioscience, biotechnology, and biochemistry 20010201

Title: Purification and characterization of an aminopeptidase from the edible basidiomycete Grifola frondosa.

Journal: Bioscience, biotechnology, and biochemistry 20010201

Title: Adult T-cell leukemia associated with gastric carcinoma: report of a case.

Journal: Surgery today 20010101

Title: In vitro and in vivo evaluation of aminopeptidase inhibitors as antimicrosporidial therapies.

Journal: The Journal of eukaryotic microbiology 20010101

Title: Bestatin-mediated inhibition of leucine aminopeptidase may hinder HIV infection.

Journal: Antiviral research 19971201

Title: Cryptosporidium parvum metalloaminopeptidase inhibitors prevent in vitro excystation.

Journal: Antimicrobial agents and chemotherapy 19961201

Title: In vitro metabolism of an insect neuropeptide by neural membrane preparations from Lymantria dispar.

Journal: Peptides 19960101

Title: Metabolism of aspartame by human and pig intestinal microvillar peptidases.

Journal: The Biochemical journal 19940315

Title: Inhibition of bovine lens leucine aminopeptidase by bestatin: number of binding sites and slow binding of this inhibitor.

Journal: Biochemistry 19930126

Title: Protease activities in carp retina.

Journal: Neurochemistry international 19921201

Title: Feedback inhibition of met-enkephalin release from the rat spinal cord in vivo.

Journal: Synapse (New York, N.Y.) 19920501

Title: Opioid control of the in vitro release of cholecystokinin-like material from the rat substantia nigra.

Journal: Journal of neurochemistry 19920301

Title: alpha-Keto amide inhibitors of aminopeptidases.

Journal: Journal of medicinal chemistry 19920207

Title: Inhibition of tumor invasion and extracellular matrix degradation by ubenimex (bestatin).

Journal: Clinical & experimental metastasis 19920101

Title: [Combination therapy of chronic myelogenous leukemia with busulfan and bestatin].

Journal: Gan to kagaku ryoho. Cancer & chemotherapy 19910401

Title: Leukotriene A4 hydrolase. Inhibition by bestatin and intrinsic aminopeptidase activity establish its functional resemblance to metallohydrolase enzymes.

Journal: The Journal of biological chemistry 19910125

Title: Tonic suppression of baroreceptor reflex by endogenous neurotensin in the rat.

Journal: Regulatory peptides 19900327

Title: Role of a serine endopeptidase in the hydrolysis of exogenous cholecystokinin by brain slices.

Journal: Neuroscience 19890101

Title: Effects of bestatin and phosphoramidon on the hypertensive response to physostigmine in the rat.

Journal: Fundamental & clinical pharmacology 19870101

Title: Isolation of two forms of the high-molecular-mass serine protease, ingensin, from porcine skeletal muscle.

Journal: FEBS letters 19850909

Title: Hossain A, et al. Protective effects of bestatin in the retina of streptozotocin-induced diabetic mice. Exp Eye Res. 2016 Aug;149:100-6

Title: Qian X, et al. Inhibition of p38 MAPK Phosphorylation Is Critical for Bestatin to Enhance ATRA-Induced Cell Differentiation in Acute Promyelocytic Leukemia NB4 Cells. Am J Ther. 2016 May-Jun;23(3):e680-9.

Title: Lis M, et al. The effects of bestatin on humoral response to sheep erythrocytes in non-treated and cyclophosphamide-immunocompromised mice. Immunopharmacol Immunotoxicol. 2013 Feb;35(1):133-8

Title: Poloz Y, et al. Bestatin inhibits cell growth, cell division, and spore cell differentiation in Dictyostelium discoideum. Eukaryot Cell. 2012 Apr;11(4):545-57

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Tags:58970-76-6 Molecular Formula|58970-76-6 MDL|58970-76-6 SMILES|58970-76-6 (2S)-2-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido]-4-methylpentanoic acid