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52-52-8,MFCD00001381
Catalog No.:AA0034L0

52-52-8 | Cycloleucine

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Purity
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1g
95%
in stock  
$10.00   $7.00
- +
5g
98%
in stock  
$17.00   $12.00
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10g
98%
in stock  
$22.00   $15.00
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25g
95%
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$45.00   $31.00
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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:
AA0034L0
Chemical Name:
Cycloleucine
CAS Number:
52-52-8
Molecular Formula:
C6H11NO2
Molecular Weight:
129.1570
MDL Number:
MFCD00001381
SMILES:
OC(=O)C1(N)CCCC1
NSC Number:
1026
Properties
Properties
 
BP:
239.22°C (rough estimate)  
Form:
Solid  
MP:
300 °C  
Refractive Index:
1.4827 (estimate)  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
127  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
9  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
1  
XLogP3:
-2.6  

Upstream Synthesis Route

[1]JournalofMedicinalChemistry,1984,vol.27,#12,p.1663-1668

[2]EuropeanJournalofMedicinalChemistry,2001,vol.36,#3,p.265-286

[3]ActaChimicaSlovenica,2012,vol.59,#3,p.680-685,6

[4]ActaChimicaSlovenica,2012,vol.59,#3,p.680-685

[5]JournaloftheChemicalSociety,1960,p.2119-2132

[6]Pharmazie,1996,vol.51,#1,p.25-27

[7]EuropeanJournalofMedicinalChemistry,2008,vol.43,#6,p.1199-1205

[1]ACSCombinatorialScience,2016,vol.18,#6,p.330-336

[2]BulletinoftheChemicalSocietyofJapan,1963,vol.36,p.34-37

[1]EuropeanJournalofMedicinalChemistry,2001,vol.36,#3,p.265-286

[2]JournalofOrganicChemistry,1958,vol.23,p.964,967

[3]ACSCombinatorialScience,2016,vol.18,#6,p.330-336

[1]JournalofOrganicChemistry,1958,vol.23,p.964,967

[1]JournalofOrganicChemistry,1958,vol.23,p.964,967

Downstream Synthesis Route

[1]ACSCombinatorialScience,2016,vol.18,p.330-336

[2]BulletinoftheChemicalSocietyofJapan,1963,vol.36,p.34-37

[1]Farmaco,EdizioneScientifica,1966,vol.21,p.624-630

[1]JournaloftheChemicalSocietyA:Inorganic,Physical,Theoretical,1966,p.1268-1275

[1]JournaloftheChemicalSociety,1962,p.4601-4607

[1]JournaloftheChemicalSociety,1962,p.4601-4607

[2]Patent:US7030114,2006,B1.Locationinpatent:Page/Pagecolumn53;50

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Journal: Pharmacology, biochemistry, and behavior 20030101

Title: Roles of ionotropic glutamate receptors in early developing neurons derived from the P19 mouse cell line.

Journal: Journal of biomedical science 20030101

Title: Actions of Group I and Group II metabotropic glutamate receptor ligands on 5-hydroxytryptamine release in the rat cerebral cortex in vivo: differential roles in the regulation of central serotonergic neurotransmission.

Journal: Neuroscience 20030101

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Title: Dual modulation of gabaergic transmission by metabotropic glutamate receptors in rat ventral tegmental area.

Journal: Neuroscience 20030101

Title: Characterisation of methionine adenosyltransferase from Mycobacterium smegmatis and M. tuberculosis.

Journal: BMC microbiology 20030101

Title: Effects of a selective metabotropic glutamate receptor agonist on the micturition reflex pathway in urethane-anesthetized rats.

Journal: Neurourology and urodynamics 20030101

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Title: Reduced activity of hippocampal group-I metabotropic glutamate receptors in learning-prone rats.

Journal: Neuroscience 20030101

Title: Acamprosate inhibits the binding and neurotoxic effects of trans-ACPD, suggesting a novel site of action at metabotropic glutamate receptors.

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Title: A pharmacological analysis of the contractile effects of glutamate on rat and human isolated gut smooth muscle strips.

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Title: Cell type-selective expression of green fluorescent protein and the calcium indicating protein, yellow cameleon, in rat cortical primary cultures.

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Title: Enantioselective synthesis of the excitatory amino acid (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid.

Journal: The Journal of organic chemistry 20021101

Title: Carbon monoxide and metabotropic glutamate receptors in rat nucleus tractus solitarii: participation in cardiovascular effect.

Journal: European journal of pharmacology 20021101

Title: Synthesis and pharmacology of 3-hydroxy-delta2-isoxazoline-cyclopentane analogues of glutamic acid.

Journal: Farmaco (Societa chimica italiana : 1989) 20021101

Title: A bicyclic cispentacin derivative as a novel reverse turn inducer in a GnRH mimetic.

Journal: The Journal of organic chemistry 20021004

Title: Group I metabotropic glutamate receptor-mediated enhancement of dopamine cell burst firing in rat ventral tegmental area in vitro.

Journal: Brain research 20020906

Title: Metabotropic glutamate receptors control gating of spike transmission in the hippocampus area CA1.

Journal: Pharmacology, biochemistry, and behavior 20020901

Title: Activation of brainstem metabotropic glutamate receptors inhibits spinal nociception in adult rats.

Journal: Pharmacology, biochemistry, and behavior 20020901

Title: Metabotropic and NMDA glutamate receptor interactions with osmotic stimuli in supraoptic neurons.

Journal: Pharmacology, biochemistry, and behavior 20020901

Title: Spatial segregation and interaction of calcium signalling mechanisms in rat hippocampal CA1 pyramidal neurons.

Journal: The Journal of physiology 20020901

Title: Activation of glutamate receptors inhibits Na/K-ATPase of cerebellum granule cells.

Journal: Biochemistry. Biokhimiia 20020901

Title: The activation of metabotropic glutamate receptors differentially affects GABA and alpha-melanocyte stimulating hormone release from the hypothalamus and the posterior pituitary of male rats.

Journal: Neuroscience letters 20020719

Title: Effects of excitatory modulation on intrinsic properties of turtle motoneurons.

Journal: Journal of neurophysiology 20020701

Title: Mimicry of host-defense peptides by unnatural oligomers: antimicrobial beta-peptides.

Journal: Journal of the American Chemical Society 20020626

Title: Tolerance of acyclic residues in the beta-peptide 12-helix: access to diverse side-chain arrays for biological applications.

Journal: Journal of the American Chemical Society 20020619

Title: Ionotropic glutamate receptors mediate juvenile hormone synthesis in the cockroach, Diploptera punctata.

Journal: Insect biochemistry and molecular biology 20020601

Title: cis-2-aminocyclopentanecarboxylic acid oligomers adopt a sheetlike structure: switch from helix to nonpolar strand.

Journal: Angewandte Chemie (International ed. in English) 20020517

Title: Effect of ionotropic and metabotropic glutamate agonists and D-aspartate on prolactin release from anterior pituitary cells.

Journal: Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association 20020501

Title: Synthesis, conformational analysis, and spectroscopic characterization of peptides based on Daf, the first rigid transition-metal receptor, cyclic C(alpha,alpha)-disubstituted glycine.

Journal: Biopolymers 20020415

Title: Highly diastereoselective nitrone cycloaddition onto a chiral ketene equivalent: asymmetric synthesis of cispentacin.

Journal: Organic letters 20020404

Title: Modulation of dendritic release of dopamine by metabotropic glutamate receptors in rat substantia nigra.

Journal: Biochemical pharmacology 20020401

Title: Stereoselective synthesis of (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid via C-H insertion of alkylidenecarbene.

Journal: Bioscience, biotechnology, and biochemistry 20020401

Title: Overcoming drug-resistant yeast infections.

Journal: Drug discovery today 20020315

Title: Cellular mechanisms of the slow (<1 Hz) oscillation in thalamocortical neurons in vitro.

Journal: Neuron 20020314

Title: Chronic ethanol treatment and withdrawal alter ACPD-evoked calcium signals in developing Purkinje neurons.

Journal: Alcoholism, clinical and experimental research 20020301

Title: Neuroprotective effects of N-acetylaspartylglutamate in a neonatal rat model of hypoxia-ischemia.

Journal: European journal of pharmacology 20020222

Title: Presynaptic inhibition of GABAergic miniature currents by metabotropic glutamate receptor in the rat CNS.

Journal: Neuroscience 20020101

Title: Glutamate induces different neuronal conditioned responses than ACPD when used as a locally ionophoresed unconditioned stimulus in the cat motor cortex.

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Title: Magnesium decreases arterial pressure and inhibits cardiovascular responses induced by N-methyl-D-aspartate and metabotropic glutamate receptors stimulation in rostral ventrolateral medulla.

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Title: Retrograde modulation of transmitter release by postsynaptic subtype 1 metabotropic glutamate receptors in the rat cerebellum.

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Title: Methionine depletion induces transcription of the mRNA (N6-adenosine)methyltransferase.

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Title: (1R,3S)-1-Aminocyclopentane-1,3-dicarboxylic acid (RS-ACPD) reduces intracellular glutamate levels in astrocytes.

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Title: Visualization of IP(3) dynamics reveals a novel AMPA receptor-triggered IP(3) production pathway mediated by voltage-dependent Ca(2+) influx in Purkinje cells.

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Title: Separation, identification, and quantification of amino acids in L-lysine fermentation potato juices by gas chromatography-mass spectrometry.

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Title: Metabotropic glutamate receptors stimulate phospholipase D via different pathways in the adult and neonate rat hippocampus.

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Title: Activation of a latent respiratory motor pathway by stimulation of neurons in the medullary chemoreceptor area of the rat.

Journal: Experimental neurology 20010901

Title: Activation of metabotropic glutamate receptor 1 accelerates NMDA receptor trafficking.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20010815

Title: An efficient route to either enantiomer of trans-2-aminocyclopentanecarboxylic acid.

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Title: Role of metabotropic glutamate receptors in vasopressin and oxytocin release.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20010801

Title: Changes in rat serum corticosterone after treatment with metabotropic glutamate receptor agonists or antagonists.

Journal: Journal of neuroendocrinology 20010801

Title: Ca2+-dependent regulation of synaptic delta2 glutamate receptor density in cultured rat Purkinje neurons.

Journal: The European journal of neuroscience 20010701

Title: mGluR1-mediated potentiation of NMDA receptors involves a rise in intracellular calcium and activation of protein kinase C.

Journal: Neuropharmacology 20010601

Title: Stimulation of Na-K-2Cl cotransporter in neurons by activation of Non-NMDA ionotropic receptor and group-I mGluRs.

Journal: Journal of neurophysiology 20010601

Title: The M1 receptor is required for muscarinic activation of mitogen-activated protein (MAP) kinase in murine cerebral cortical neurons.

Journal: The Journal of biological chemistry 20010511

Title: Inhibition of choline acetyltransferase by excitatory amino acids as a possible mechanism for cholinergic dysfunction in the central nervous system.

Journal: Journal of neurochemistry 20010501

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Journal: Zhongguo ying yong sheng li xue za zhi = Zhongguo yingyong shenglixue zazhi = Chinese journal of applied physiology 20010501

Title: The metabotropic glutamate receptor agonist 1S,3R-ACPD stimulates and modulates NMDA receptor mediated excitotoxicity in organotypic hippocampal slice cultures.

Journal: Brain research 20010413

Title: Group I metabotropic glutamate receptors are expressed in the chicken retina and by cultured retinal amacrine cells.

Journal: Journal of neurochemistry 20010401

Title: Expression and regulation of Na pump isoforms in cultured cerebellar granule cells.

Journal: Neuroreport 20010326

Title: Tetanic stimulation and metabotropic glutamate receptor agonists modify synaptic responses and protein kinase activity in rat auditory cortex.

Journal: Brain research 20010316

Title: Protein kinase C activation modulates alpha-calmodulin kinase II binding to NR2A subunit of N-methyl-D-aspartate receptor complex.

Journal: The Journal of biological chemistry 20010309

Title: PLC-beta1, activated via mGluRs, mediates activity-dependent differentiation in cerebral cortex.

Journal: Nature neuroscience 20010301

Title: Activation of metabotropic glutamate receptors induces gamma frequency oscillations in the rat dentate gyrus in vivo.

Journal: Neuropharmacology 20010301

Title: Task-dependent role for dorsal striatum metabotropic glutamate receptors in memory.

Journal: Learning & memory (Cold Spring Harbor, N.Y.) 20010301

Title: Upregulation of preprodynorphin and preproenkephalin mRNA expression by selective activation of group I metabotropic glutamate receptors in characterized primary cultures of rat striatal neurons.

Journal: Brain research. Molecular brain research 20010131

Title: Regional distribution and pharmacological characteristics of [3H]N-acetyl-aspartyl-glutamate (NAAG) binding sites in rat brain.

Journal: Neurochemistry international 20010101

Title: Slow dorsal-ventral rhythm generator in the lamprey spinal cord.

Journal: Journal of neurophysiology 20010101

Title: cAMP-dependent presynaptic regulation of spontaneous glycinergic IPSCs in mechanically dissociated rat spinal cord neurons.

Journal: Journal of neurophysiology 20010101

Title: Sustained L-type calcium currents in dissociated deep dorsal horn neurons of the rat: characteristics and modulation.

Journal: Neuroscience 20010101

Title: Traumatic injury of cultured astrocytes alters inositol (1,4,5)-trisphosphate-mediated signaling.

Journal: Glia 20010101

Title: Metabotropic glutamate receptors modify ionotropic glutamate responses in neocortical pyramidal cells and interneurons.

Journal: Experimental brain research 20010101

Title: Developmental changes in the modulation of cyclic amp accumulation by activation of metabotropic glutamate receptors.

Journal: Polish journal of pharmacology 20010101

Title: Locomotor activity and accumbens Fos expression driven by ventral hippocampal stimulation require D1 and D2 receptors.

Journal: Neuroscience 19990101

Title: Behavioral activity of 1S,3R-ACPD, an agonist of metabotropic glutamate receptors.

Journal: Polish journal of pharmacology 19970801

Title: Pharmacological characterization of 1-aminoindan-1,5-dicarboxylic acid, a potent mGluR1 antagonist.

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Title: Anti-Candida activity of cispentacin: the active transport by amino acid permeases and possible mechanisms of action.

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Title: Effects of D-cycloserine and cycloleucine, ligands for the NMDA-associated strychnine-insensitive glycine site, on brain-stimulation reward and spontaneous locomotion.

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Tags:52-52-8 Molecular Formula|52-52-8 MDL|52-52-8 SMILES|52-52-8 Cycloleucine