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2116-55-4 | 1(4H)-Pyridinepropanoic acid, α-amino-3-hydroxy-4-oxo-
CAS No: 2116-55-4 Catalog No: AG0005N6 MDL No:
Product Description
Catalog Number:
AG0005N6
Chemical Name:
1(4H)-Pyridinepropanoic acid, α-amino-3-hydroxy-4-oxo-
CAS Number:
2116-55-4
Molecular Formula:
C8H10N2O4
Molecular Weight:
198.1760
IUPAC Name:
2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoic acid
InChI:
InChI=1S/C8H10N2O4/c9-5(8(13)14)3-10-2-1-6(11)7(12)4-10/h1-2,4-5,12H,3,9H2,(H,13,14)
InChI Key:
WZNJWVWKTVETCG-UHFFFAOYSA-N
SMILES:
OC(=O)C(Cn1ccc(=O)c(c1)O)N
Properties
Complexity:
321
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
198.064g/mol
Formal Charge:
0
Heavy Atom Count:
14
Hydrogen Bond Acceptor Count:
6
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
198.178g/mol
Monoisotopic Mass:
198.064g/mol
Rotatable Bond Count:
3
Topological Polar Surface Area:
104A^2
Undefined Atom Stereocenter Count:
1
Undefined Bond Stereocenter Count:
0
XLogP3:
-3.5
Literature
| Title | Journal |
|---|---|
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| Productive performance and urinary excretion of mimosine metabolites by hair sheep grazing in a silvopastoral system with high densities of Leucaena leucocephala. | Tropical animal health and production 20121201 |
| Prolyl hydroxylase inhibitors increase the production of vascular endothelial growth factor in dental pulp-derived cells. | Journal of endodontics 20121101 |
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| A rapid and robust assay for the determination of the amino acid hypusine as a possible biomarker for a high-throughput screening of antimalarials and for the diagnosis and therapy of different diseases. | Amino acids 20120501 |
| A comparative study on mimosine, 3,4-dihydroxy pyridone (3,4-DHP) and 2,3-dihydroxy pyridone (2,3-DHP), purine derivatives (PD) excretion in the urine, thyroid hormone and blood metabolites profiles of Thai swamp buffalo (Bubalus bubalis) and Murrah buffalo (Bubalus bubalis). | Tropical animal health and production 20120401 |
| Prolyl hydroxylase inhibitors increase the production of vascular endothelial growth factor by periodontal fibroblasts. | Journal of periodontal research 20120401 |
| L-Mimosine blocks cell proliferation via upregulation of B-cell translocation gene 2 and N-myc downstream regulated gene 1 in prostate carcinoma cells. | American journal of physiology. Cell physiology 20120215 |
| Mimosine arrests the cell cycle prior to the onset of DNA replication by preventing the binding of human Ctf4/And-1 to chromatin via Hif-1α activation in HeLa cells. | Cell cycle (Georgetown, Tex.) 20120215 |
| Mimosine-induced apoptosis in C6 glioma cells requires the release of mitochondria-derived reactive oxygen species and p38, JNK activation. | Neurochemical research 20120201 |
| Transient hypoxia-inducible factor activation in rat renal ablation and reduced fibrosis with L-mimosine. | Nephrology (Carlton, Vic.) 20120101 |
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| Overexpression of eIF3a in Squamous Cell Carcinoma of the Oral Cavity and Its Putative Relation to Chemotherapy Response. | Journal of oncology 20120101 |
| Solid-phase synthesis of mimosine tetrapeptides and their inhibitory activities on neuraminidase and tyrosinase. | Journal of agricultural and food chemistry 20111228 |
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| N-myc downstream regulated gene1/Cap43 overexpression suppresses tumor growth by hepatic cancer cells through cell cycle arrest at the G0/G1 phase. | Cancer letters 20111101 |
| Curcumin provides potential protection against the activation of hypoxia and prolyl 4-hydroxylase inhibitors on prostate-specific antigen expression in human prostate carcinoma cells. | Molecular nutrition & food research 20111101 |
| Upregulation of hypoxia-inducible factor 1 alpha in local vein wall is associated with enhanced venous thrombus resolution. | Thrombosis research 20111001 |
| Inhibitory effect of mimosine on polyphenoloxidase from cephalothoraxes of Pacific white shrimp (Litopenaeus vannamei). | Journal of agricultural and food chemistry 20110928 |
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| Pretreatment with intracoronary mimosine improves postischemic myocardial functional recovery. | Surgery 20110801 |
| RBE of α-particles from (211)At for complex DNA damage and cell survival in relation to cell cycle position. | International journal of radiation biology 20110401 |
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| FDA-approved drugs that protect mammalian neurons from glucose toxicity slow aging dependent on cbp and protect against proteotoxicity. | PloS one 20110101 |
| Partial purification and characterization of polyphenoloxidase from culinary-medicinal Royal Sun mushroom (the Himematsutake), Agaricus brasiliensis S. Wasser et al. (Agaricomycetideae). | International journal of medicinal mushrooms 20110101 |
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| Cell cycle-dependent regulation of the forkhead transcription factor FOXK2 by CDK·cyclin complexes. | The Journal of biological chemistry 20101112 |
| Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. | Bioorganic & medicinal chemistry letters 20101101 |
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| A key commitment step in erythropoiesis is synchronized with the cell cycle clock through mutual inhibition between PU.1 and S-phase progression. | PLoS biology 20100901 |
| Etoposide Reduces Peroxynitrite-Induced Cytotoxicity via Direct Scavenging Effect. | Experimental neurobiology 20100901 |
| Xanthine oxidase/tyrosinase inhibiting, antioxidant, and antifungal oxindole alkaloids from Isatis costata. | Pharmaceutical biology 20100601 |
| Transgenic Leucaena leucocephala expressing the Rhizobium gene pydA encoding a meta-cleavage dioxygenase shows reduced mimosine content. | Plant physiology and biochemistry : PPB 20100401 |
| Cloning and expression of SOLD1 in ovine and caprine placenta, and their expected roles during the development of placentomes. | BMC developmental biology 20100101 |
| Cytometry of chromatin bound Mcm6 and PCNA identifies two states in G1 that are separated functionally by the G1 restriction point. | BMC cell biology 20100101 |
| Expression of human eukaryotic initiation factor 3f oscillates with cell cycle in A549 cells and is essential for cell viability. | Cell division 20100101 |
| Ribonucleoprotein particles containing non-coding Y RNAs, Ro60, La and nucleolin are not required for Y RNA function in DNA replication. | PloS one 20100101 |
| Impaired cell cycle regulation of the osteoblast-related heterodimeric transcription factor Runx2-Cbfbeta in osteosarcoma cells. | Journal of cellular physiology 20091201 |
| SUMO modification regulates BLM and RAD51 interaction at damaged replication forks. | PLoS biology 20091201 |
| Prolyl hydroxylase inhibitors increase neoangiogenesis and callus formation following femur fracture in mice. | Journal of orthopaedic research : official publication of the Orthopaedic Research Society 20091001 |
| Variations in IC(50) values with purity of mushroom tyrosinase. | International journal of molecular sciences 20090901 |
| The carboxyl terminus of Brca2 links the disassembly of Rad51 complexes to mitotic entry. | Current biology : CB 20090714 |
| Aurora B kinase inhibition in mitosis: strategies for optimising the use of aurora kinase inhibitors such as AT9283. | Cell cycle (Georgetown, Tex.) 20090615 |
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| Purification and partial characterization of lignin peroxidase from Acinetobacter calcoaceticus NCIM 2890 and its application in decolorization of textile dyes. | Applied biochemistry and biotechnology 20090101 |
| Synthesis of 4-pyridone-3-sulfate and an improved synthesis of 3-hydroxy-4-pyridone. | Chemistry Central journal 20090101 |
| The probability to initiate X chromosome inactivation is determined by the X to autosomal ratio and X chromosome specific allelic properties. | PloS one 20090101 |
| Persistently elevated level of IL-8 in Chlamydia trachomatis infected HeLa 229 cells is dependent on intracellular available iron. | Mediators of inflammation 20090101 |
| Inhibition of HIV-1 gene expression by Ciclopirox and Deferiprone, drugs that prevent hypusination of eukaryotic initiation factor 5A. | Retrovirology 20090101 |
| Pyruvate carboxylase is involved in metabolism of mimosine by Rhizobium sp. strain TAL1145. | Archives of microbiology 20081001 |
| Multiple cellular mechanisms related to cyclin A1 in prostate cancer invasion and metastasis. | Journal of the National Cancer Institute 20080716 |
| The cloned 1-aminocyclopropane-1-carboxylate (ACC) deaminase gene from Sinorhizobium sp. strain BL3 in Rhizobium sp. strain TAL1145 promotes nodulation and growth of Leucaena leucocephala. | Systematic and applied microbiology 20080601 |
| Gut microbiology - broad genetic diversity, yet specific metabolic niches. | Animal : an international journal of animal bioscience 20080501 |
| Centrosome duplication proceeds during mimosine-induced G1 cell cycle arrest. | Journal of cellular physiology 20080401 |
| S-phase progression stimulates both the mutagenic KU-independent pathway and mutagenic processing of KU-dependent intermediates, for nonhomologous end joining. | Oncogene 20080313 |
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| Inhibition of hypoxia inducible factor hydroxylases protects against renal ischemia-reperfusion injury. | Journal of the American Society of Nephrology : JASN 20080101 |
| Kinetic properties of hexameric tyrosinase from the crustacean Palinurus elephas. | Photochemistry and photobiology 20080101 |
| A negative modulatory role for rho and rho-associated kinase signaling in delamination of neural crest cells. | Neural development 20080101 |
| Identification of G1-regulated genes in normally cycling human cells. | PloS one 20080101 |
| Cell cycle related modulations in Runx2 protein levels are independent of lymphocyte enhancer-binding factor 1 (Lef1) in proliferating osteoblasts. | Journal of molecular histology 20071001 |
| Deferiprone in the treatment of transfusion-dependent thalassemia: a review and perspective. | Therapeutics and clinical risk management 20071001 |
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| Inhibiting survivin expression enhances TRAIL-induced tumoricidal activity in human hepatocellular carcinoma via cell cycle arrest. | Cancer biology & therapy 20070801 |
| Mimosine mitigates oxidative stress in selenium deficient seedlings of Vigna radiata--Part I: Restoration of mitochondrial function. | Biological trace element research 20070701 |
| The pydA-pydB fusion gene produces an active dioxygenase-hydrolase that degrades 3-hydroxy-4-pyridone, an intermediate of mimosine metabolism. | Applied microbiology and biotechnology 20070601 |
| Studies on cell-cycle synchronization in the asexual erythrocytic stages of Plasmodium falciparum. | Parasitology 20070301 |
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| Cell cycle-dependent association of Rad51 with the nuclear matrix. | DNA and cell biology 20070101 |
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| Modulation of differentiation-related gene 1 expression by cell cycle blocker mimosine, revealed by proteomic analysis. | Molecular & cellular proteomics : MCP 20050701 |
| Structure-activity relationships of tyrosinase inhibitory combinatorial library of 2,5-disubstituted-1,3,4-oxadiazole analogues. | Bioorganic & medicinal chemistry 20050516 |
| Induction of hypoxia inducible factor-1 attenuates metabolic insults induced by 3-nitropropionic acid in rat C6 glioma cells. | Journal of neurochemistry 20050501 |
| Resveratrol-mediated sensitisation to TRAIL-induced apoptosis depends on death receptor and mitochondrial signalling. | European journal of cancer (Oxford, England : 1990) 20050301 |
| Iron-mediated H2O2 production as a mechanism for cell type-specific inhibition of tumor necrosis factor alpha-induced but not interleukin-1beta-induced IkappaB kinase complex/nuclear factor-kappaB activation. | The Journal of biological chemistry 20050128 |
| Mimosine attenuates serine hydroxymethyltransferase transcription by chelating zinc. Implications for inhibition of DNA replication. | The Journal of biological chemistry 20050107 |
| Inhibition of MCP-1 and MIP-2 chemokines in murine trichinellosis: effect of the anti-inflammatory compound L-mimosine. | International journal of immunopathology and pharmacology 20050101 |
| Immediate transfection of patient-derived leukemia: a novel source for generating cell-based vaccines. | Genetic vaccines and therapy 20050101 |
| P-glycoprotein expression is induced in human pancreatic cancer xenografts during treatment with a cell cycle regulator, mimosine. | Pathology oncology research : POR 20050101 |
| Progesterone receptor and the cell cycle modulate apoptosis in granulosa cells. | Endocrinology 20041101 |
| Cell cycle arrest at the initiation step of human chromosomal DNA replication causes DNA damage. | Journal of cell science 20041001 |
| A novel nucleolar protein, PAPA-1, induces growth arrest as a result of cell cycle arrest at the G1 phase. | Gene 20040929 |
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| Role of eIF3 p170 in controlling synthesis of ribonucleotide reductase M2 and cell growth. | Oncogene 20040506 |
| AML1/RUNX1 increases during G1 to S cell cycle progression independent of cytokine-dependent phosphorylation and induces cyclin D3 gene expression. | The Journal of biological chemistry 20040409 |
| Do calcium-mediated cellular signalling pathways, prostaglandin E2 (PGE2), estrogen or progesterone receptor antagonists, or bacterial endotoxins affect bovine placental function in vitro? | Prostaglandins & other lipid mediators 20040401 |
| p53-independent induction of p21(waf1/cip1) contributes to the activation of caspases in GTP-depletion-induced apoptosis of insulin-secreting cells. | Cell death and differentiation 20040101 |
| Sensitization for tumor necrosis factor-related apoptosis-inducing ligand-induced apoptosis by the chemopreventive agent resveratrol. | Cancer research 20040101 |
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| S phase progression is required for transcriptional activation of the beta-phaseolin promoter. | The Journal of biological chemistry 20031114 |
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| Activation of the hypoxia-inducible factor-pathway and stimulation of angiogenesis by application of prolyl hydroxylase inhibitors. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20030601 |
| Cell cycle inhibition mediated by the outer surface of the C/EBPalpha basic region is required but not sufficient for granulopoiesis. | Oncogene 20030501 |
| Participation of kin17 protein in replication factories and in other DNA transactions mediated by high molecular weight nuclear complexes. | Molecular cancer research : MCR 20030501 |
| Asynchronous replication timing of imprinted loci is independent of DNA methylation, but consistent with differential subnuclear localization. | Genes & development 20030315 |
| Truffle thio-flavours reversibly inhibit truffle tyrosinase. | FEMS microbiology letters 20030314 |
| Protein 4.1N is required for translocation of inositol 1,4,5-trisphosphate receptor type 1 to the basolateral membrane domain in polarized Madin-Darby canine kidney cells. | The Journal of biological chemistry 20030207 |
| The mid genes of Rhizobium sp strain TAL1145 are required for degradation of mimosine into 3-hydroxy-4-pyridone and are inducible by mimosine. | Microbiology (Reading, England) 20030201 |
| Latent HIV-1 reactivation in transgenic mice requires cell cycle -dependent demethylation of CREB/ATF sites in the LTR. | AIDS (London, England) 20030124 |
| PDGF upregulates delayed rectifier via Src family kinases and sphingosine kinase in oligodendroglial progenitors. | American journal of physiology. Cell physiology 20030101 |
| Effect of the compound L-mimosine in an in vivo model of chronic granuloma formation induced by potassium permanganate (KMNO4). | International journal of immunopathology and pharmacology 20030101 |
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| Mimosine, a plant-derived amino acid induces apoptosis in human pancreatic cancer xenografts. | Anticancer research 20030101 |
| Enantioseparation of chiral aromatic amino acids by capillary electrophoresis in neutral and charged cyclodextrin selector modes. | Electrophoresis 20021201 |
| Ultraviolet light-induced apoptosis is associated with S-phase in primary human fibroblasts. | DNA repair 20021001 |
| Engineering bacterial competitiveness and persistence in the phytosphere. | Molecular plant-microbe interactions : MPMI 20020901 |
| Association between the cell cycle and neural crest delamination through specific regulation of G1/S transition. | Developmental cell 20020901 |
| Differential effects of cyclin-dependent kinase blockers upon cell death in the developing retina. | Brain research 20020823 |
| Cell-cycle-dependent regulation of CNT1, a concentrative nucleoside transporter involved in the uptake of cell-cycle-dependent nucleoside-derived anticancer drugs. | Biochemical and biophysical research communications 20020823 |
| The antifungal drug ciclopirox inhibits deoxyhypusine and proline hydroxylation, endothelial cell growth and angiogenesis in vitro. | International journal of cancer 20020801 |
| Mimosine prevents the death of glucose-deprived immunostimulated astrocytes by scavenging peroxynitrite. | Glia 20020701 |
| Inhibition of ultraviolet B (UVB) induced apoptosis in A431 cells by mimosine is not dependent on cell cycle arrest. | Canadian journal of physiology and pharmacology 20020701 |
| Tuning up or down the UV-induced apoptosis in Chinese hamster ovary cells with cell cycle inhibitors. | Photochemistry and photobiology 20020601 |
| A novel association of the SMN protein with two major non-ribosomal nucleolar proteins and its implication in spinal muscular atrophy. | Human molecular genetics 20020501 |
| Ultraviolet-B-induced G1 arrest is mediated by downregulation of cyclin-dependent kinase 4 in transformed keratinocytes lacking functional p53. | The Journal of investigative dermatology 20020501 |
| Profiling and screening analysis of 27 aromatic amino acids by capillary electrophoresis in dual modes. | Electrophoresis 20020401 |
| Modulation of intrinsic P-glycoprotein expression in multicellular prostate tumor spheroids by cell cycle inhibitors. | Biochimica et biophysica acta 20020213 |
| Survivin exists in immunochemically distinct subcellular pools and is involved in spindle microtubule function. | Journal of cell science 20020201 |
| Homologous recombination induced by replication inhibition, is stimulated by expression of mutant p53. | Oncogene 20020117 |
| CCAAT/enhancer binding protein alpha uses distinct domains to prolong pituitary cells in the growth 1 and DNA synthesis phases of the cell cycle. | BMC cell biology 20020101 |
| Inhibition of MCP-1 and MIP-2 transcription and translation by mimosine in muscle tissue infected with the parasite Trichinella spiralis. | Molecular and cellular biochemistry 20020101 |
| The deoxyribo-mode expression of primase activities of the primase-alpha DNA polymerase enzyme complex associated with nucleoprotein complexes harboring an extrachromosomal DNA identical with avian myeloblastosis virus core-bound DNA: influencing by carbonyldiphosphonate, mimosine and butylphenyl deoxyguanosine-5'-triphosphate. | Acta virologica 20020101 |
| Identification of promoter elements responsible for transcriptional inhibition of polo-like kinase 1 and topoisomerase IIalpha genes by p21(WAF1/CIP1/SDI1). | Cell cycle (Georgetown, Tex.) 20020101 |
| S-phase synchronized CHO cells show elevated transfection efficiency and expression using CaPi. | Cytotechnology 20020101 |
| Lymphoblasts already in the DNA synthesis phase of the cell cycle can be reversibly arrested at the R/G transition. | Chromosoma 20011201 |
| Methylation of episomal plasmids as a barrier to transient gene expression via a synthetic delivery vector. | Biomolecular engineering 20011031 |
| A DNA polymerase epsilon inhibitor activates the ribo and deoxyribo modes of primase expression and induces a unique phenomenon of primer accumulation. | FEBS letters 20010907 |
| Characterization of homologous recombination induced by replication inhibition in mammalian cells. | The EMBO journal 20010716 |
| 8-Cl-cAMP induces cell cycle-specific apoptosis in human cancer cells. | International journal of cancer 20010701 |
| Selection of several classes of mimosine-degradation-defective Tn3Hogus-insertion mutants of Rhizobium sp. strain TAL1145 on the basis of mimosine-inducible GUS activity. | Canadian journal of microbiology 20010601 |
| Methods for synchronizing cells at specific stages of the cell cycle. | Current protocols in cell biology 20010501 |
| Cell cycle-related changes in regulatory volume decrease and volume-sensitive chloride conductance in mouse fibroblasts. | Journal of cellular physiology 20010401 |
| Drought associated poisoning of cattle in South Texas by the high quality forage legume Leucaena leucocephala. | Veterinary and human toxicology 20010401 |
| Partial purification, characterization, and histochemical localization of fully latent desert truffle (Terfezia claveryi Chatin) polyphenol oxidase. | Journal of agricultural and food chemistry 20010401 |
| Anatomy of the primase-alpha DNA polymerase reaction accomplished by nucleoprotein complexes harboring an extrachromosomal DNA identical with avian myeloblastosis virus core-bound DNA: influencing by carbonyldiphosphonate, mimosine and butylphenyl deoxyguanosine-5'-triphosphate. | Acta virologica 20010401 |
| Kinetic analyses of mitochondrial 75selenium uptake in Trigonella foenum-graecum seedlings exposed to selenium and mimosine. | Biological trace element research 20010301 |
| MCM3AP, a novel acetyltransferase that acetylates replication protein MCM3. | EMBO reports 20010215 |
| Radiation sensitization of mammalian cells by metal chelators. | Radiation research 20010201 |
| De novo activation of the beta-phaseolin promoter by phosphatase or protein synthesis inhibitors. | The Journal of biological chemistry 20010119 |
| Prevention of entrance into G2 cell cycle phase by mimosine decreases locomotion of cells from the tumor cell line SW480. | Cancer letters 20010101 |
| Uptake of 45Ca by mitochondria of Trigonella foenum-graecum as influenced by selenium and mimosine--detailed kinetic analyses. | Biological trace element research 20010101 |
| Modulation of cell cycle regulatory protein expression and suppression of tumor growth by mimosine in nude mice. | International journal of oncology 20001001 |
| Mimosine arrests cells in G1 by enhancing the levels of p27(Kip1). | Experimental cell research 20000110 |
| Protection from oxidative stress-induced apoptosis in cortical neuronal cultures by iron chelators is associated with enhanced DNA binding of hypoxia-inducible factor-1 and ATF-1/CREB and increased expression of glycolytic enzymes, p21(waf1/cip1), and erythropoietin. | The Journal of neuroscience : the official journal of the Society for Neuroscience 19991115 |
| Inhibitory effect of mimosine on proliferation of human lung cancer cells is mediated by multiple mechanisms. | Cancer letters 19991018 |
| Antiretroviral effects of deoxyhypusyl hydroxylase inhibitors: a hypusine-dependent host cell mechanism for replication of human immunodeficiency virus type 1 (HIV-1). | Biochemical pharmacology 19980601 |
| Submicromolar paclitaxel induces apoptosis in human gastric cancer cells at early G1 phase. | Anticancer research 19980101 |
| The effect of administration of glycine and tyrosine on the growth depression caused by mimosine in rats. | Zeitschrift fur Tierphysiologie, Tierernahrung und Futtermittelkunde 19830801 |
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