Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C6H13NO2 |
| Molecular Weight | 131.1729 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCC[C@H](N)C(O)=O
InChI
InChIKey=LRQKBLKVPFOOQJ-YFKPBYRVSA-N
InChI=1S/C6H13NO2/c1-2-3-4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m0/s1
| Molecular Formula | C6H13NO2 |
| Molecular Weight | 131.1729 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Norleucine (L-norleucine) is a 2-aminohexanoic acid is an alpha-amino acid that is caproic acid substituted by an amino group at position 2. It derives from a hexanoic acid. It is used experimentally to study protein structure and function. Norleucine appears to inhibit bacterial growth due to incorporation into proteins in place of methionine, as the analogue inhibits methionine incorporation but does not significantly reduce its synthesis. L-norleucine had antiviral activity in thermophile. In vitro and in vivo assays revealed that L-norleucine significantly suppressed metastasis of gastric and breast cancer cells. L-norleucine interacted with hnRNPA2/B1 protein to inhibit the expressions of Twist1 and Snail, two inhibitors of E-cadherin, and promote the E-cadherin expression, leading to the inhibition of tumor metastasis.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Leucine in food mediates some of the postprandial rise in plasma leptin concentrations. | 2006-09 |
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| Sub-microsecond protein folding. | 2006-06-09 |
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| Assay of urinary alpha-fluoro-beta-alanine by gas chromatography-mass spectrometry for the biological monitoring of occupational exposure to 5-fluorouracil in oncology nurses and pharmacy technicians. | 2006-03 |
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| Immunohistochemical localization of advanced glycation end products in pinguecula. | 2006-01 |
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| AT4 receptor activation increases intracellular calcium influx and induces a non-N-methyl-D-aspartate dependent form of long-term potentiation. | 2006 |
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| Determination of intrinsic hydrophilicity/hydrophobicity of amino acid side chains in peptides in the absence of nearest-neighbor or conformational effects. | 2006 |
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| Oxidation and carboxy methyl lysine-modification of albumin: possible involvement in the progression of oxidative stress in hemodialysis patients. | 2005-12 |
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| Substitution of methionine 35 inhibits apoptotic effects of Abeta(31-35) and Abeta(25-35) fragments of amyloid-beta protein in PC12 cells. | 2005-11 |
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| Boro-norleucine as a P1 residue for the design of selective and potent DPP7 inhibitors. | 2005-10-01 |
|
| Nutrient regulation of PKCepsilon is mediated by leucine, not insulin, in skeletal muscle. | 2005-10 |
|
| Norleucine, a natural occurrence in a novel ergot alkaloid gamma-ergokryptinine. | 2005-08 |
|
| Neighbor effect on PPII conformation in alanine peptides. | 2005-07-27 |
|
| Observation of a tetrahedral reaction intermediate in the HIV-1 protease-substrate complex. | 2005-07-15 |
|
| Abeta(31-35) and Abeta(25-35) fragments of amyloid beta-protein induce cellular death through apoptotic signals: Role of the redox state of methionine-35. | 2005-05-23 |
|
| Identification of neurite outgrowth active sites on the laminin alpha4 chain G domain. | 2005-04-19 |
|
| Neurotoxicity and oxidative stress in D1M-substituted Alzheimer's A beta(1-42): relevance to N-terminal methionine chemistry in small model peptides. | 2005-04 |
|
| Effect of cysteine on methionine production by a regulatory mutant of Corynebacterium lilium. | 2005-02 |
|
| Granzyme M is a regulatory protease that inactivates proteinase inhibitor 9, an endogenous inhibitor of granzyme B. | 2004-12-24 |
|
| Inhibition of in vitro pyrraline formation by L-arginine and polyamines. | 2004-12 |
|
| Cyclic peptides from the loop region of the laminin alpha 4 chain LG4 module show enhanced biological activity over linear peptides. | 2004-10-26 |
|
| A fluorescent alpha-factor analogue exhibits multiple steps on binding to its G protein coupled receptor in yeast. | 2004-10-26 |
|
| Novel peptide ligands for integrin alpha 4 beta 1 overexpressed in cancer cells. | 2004-10 |
|
| Presentation and detection of azide functionality in bacterial cell surface proteins. | 2004-09-01 |
|
| Nepsilon-(Carboxymethyl)lysine and 3-DG-imidazolone are major AGE structures in protein modification by 3-deoxyglucosone. | 2004-09 |
|
| Investigation of the nature of the methionine-pi interaction in beta-hairpin peptide model systems. | 2004-09 |
|
| The stereospecificity and catalytic efficiency of the tryptophan synthase-catalysed exchange of the alpha-protons of amino acids. | 2004-08-01 |
|
| Structure/function studies of an endotoxin-neutralizing peptide derived from bactericidal/permeability-increasing protein. | 2004-08 |
|
| Dynamic relationships among type IIa bacteriocins: temperature effects on antimicrobial activity and on structure of the C-terminal amphipathic alpha helix as a receptor-binding region. | 2004-07-20 |
|
| Exploration of the P2-P3 SAR of aldehyde cathepsin K inhibitors. | 2004-07-05 |
|
| Enzymic and structural characterization of nepenthesin, a unique member of a novel subfamily of aspartic proteinases. | 2004-07-01 |
|
| A Dhb-microcystin from the filamentous cyanobacterium Planktothrix rubescens. | 2004-07 |
|
| DNA display II. Genetic manipulation of combinatorial chemistry libraries for small-molecule evolution. | 2004-07 |
|
| Age estimation from aspartic acid racemization of root dentin by internal standard method. | 2004-05-10 |
|
| Ultrasonic relaxation due to inclusion complex of amino acid by beta-cyclodextrin in aqueous solution. | 2004-05 |
|
| Determinants of high-affinity binding and receptor activation in the N-terminus of CCL-19 (MIP-3 beta). | 2004-03-30 |
|
| Comparison of C-H...pi and hydrophobic interactions in a beta-hairpin peptide: impact on stability and specificity. | 2004-02-25 |
|
| Conformational and structural analysis of the equilibrium between single- and double-strand beta-helix of a D,L-alternating oligonorleucine. | 2004-02-05 |
|
| Norleucine1-Angiotensin IV alleviates mecamylamine-induced spatial memory deficits. | 2004-02 |
|
| Engineered biosynthesis of regioselectively modified aromatic polyketides using bimodular polyketide synthases. | 2004-02 |
|
| Analysis of 6-hydroxy-2-aminocaproic acid (HACA) as a specific marker of protein oxidation: the use of N(O,S)-ethoxycarbonyl trifluoroethyl ester derivatives and gas chromatography/mass spectrometry. | 2004-02 |
|
| An approach to developing a force field for molecular simulation of martensitic phase transitions between phases with subtle differences in energy and structure. | 2004-01-14 |
|
| Tomato paste fraction inhibiting the formation of advanced glycation end-products. | 2004-01 |
|
| Evolution of phage with chemically ambiguous proteomes. | 2003-12-10 |
|
| High levels of urinary pentosidine, an advanced glycation end product, in children with acute exacerbation of atopic dermatitis: relationship with oxidative stress. | 2003-12 |
|
| Glycation in food and metabolic transit of dietary AGEs (advanced glycation end-products): studies on the urinary excretion of pyrraline. | 2003-12 |
|
| 2.0A resolution crystal structures of the ternary complexes of human phenylalanine hydroxylase catalytic domain with tetrahydrobiopterin and 3-(2-thienyl)-L-alanine or L-norleucine: substrate specificity and molecular motions related to substrate binding. | 2003-10-31 |
|
| Global incorporation of norleucine in place of methionine in cytochrome P450 BM-3 heme domain increases peroxygenase activity. | 2003-09-20 |
|
| O-glycosylation of Sp1 and transcriptional regulation of the calmodulin gene by insulin and glucagon. | 2003-09 |
|
| Synthesis, characterization and preliminary cytotoxicity assays of poly(ethylene glycol)-malonato-Pt-DACH conjugates. | 2003-08-23 |
|
| Spectroscopically determined collagen Pyr/deH-DHLNL cross-link ratio and crystallinity indices differ markedly in recombinant congenic mice with divergent calculated bone tissue strength. | 2003 |
Sample Use Guides
Rats were injected subcutaneously with various doses of Norleucine (0.5 and 5.0 umol/g body wt.) every 12 h from 3 to 15 days post partum.
Route of Administration:
Other
It was found that the dissociation
constant (Kd) of L-norleucine for hnRNPA2B1 was 4.45 ±
1.77 uM, suggesting that L-norleucine was directly bound
with hnRNPA2B1 protein. The binding of L-norleucine with RRM1 (Kd = 4.02 ± 1.48 uM) or RRM2
(Kd = 4.85 ± 0.93 uM) generated significant thermodynamic changes, while L-norleucine was not bound with the C-terminal domain (Kd was not measured).
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:19:42 GMT 2025
by
admin
on
Mon Mar 31 18:19:42 GMT 2025
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| Record UNII |
832C8OV84S
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C73539
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D009646
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36405
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C87587
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21236
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DB15458
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DTXSID70883362
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832C8OV84S
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206-321-4
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327-57-1
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m8065
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10378
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NORLEUCINE
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18347
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