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L-Norleucine

Cat No.:V30908 Purity: ≥98%
L-Norleucine ((S)-2-Aminohexanoic acid) is an enantiomer of leucine that affects protein synthesis in skeletal muscle.
L-Norleucine
L-Norleucine Chemical Structure CAS No.: 327-57-1
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10g
Other Sizes

Other Forms of L-Norleucine:

  • L-Norleucine-d9-2-Aminohexanoic acid-d9;-Norleucine-d9)
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
L-Norleucine ((S)-2-Aminohexanoic acid) is an enantiomer of leucine that affects protein synthesis in skeletal muscle.
Biological Activity I Assay Protocols (From Reference)
Targets
L-Norleucine targets branched-chain amino acid (BCAA) metabolic pathways (involved in skeletal muscle protein turnover) [1]
L-Norleucine targets tumor metastasis-related signaling pathways [2]
ln Vitro
L-norleucine, a leucine isomer, has a particular effect on protein synthesis in skeletal muscle. L-norleucine exhibits antiviral action. L-norleucine interacts with the hnRNPA2/B1 protein, decreasing the expression of two E-cadherin inhibitors, Twist1 and Snail, while increasing E-cadherin expression and inhibiting tumor spread [2].
- Skeletal muscle protein turnover regulation: In isolated rat skeletal muscle strips, L-Norleucine (5-20 mM) enhanced protein synthesis, increasing 3H-leucine incorporation into muscle proteins by 28-45% compared to control; it also inhibited protein degradation, reducing 3H-leucine release from pre-labeled muscle strips by 22-36% [1]
- Tumor metastasis inhibition: In human breast cancer cell line MDA-MB-231 and melanoma cell line B16F10, L-Norleucine (1-10 mM) dose-dependently suppressed cell migration and invasion; at 10 mM, it reduced migration rate by 58% (MDA-MB-231) and 63% (B16F10), and inhibited invasion by 49% and 55% respectively [2]
- L-Norleucine did not affect the viability of tumor cells at concentrations up to 10 mM, indicating selective inhibition of metastatic phenotypes without cytotoxicity [2]
ln Vivo
- Skeletal muscle protein metabolism modulation: In male Wistar rats, L-Norleucine administration (1 g/kg, intraperitoneal injection) increased the fractional synthesis rate (FSR) of skeletal muscle proteins by 32% and decreased the fractional degradation rate (FDR) by 25% compared to saline control; the net protein balance in skeletal muscle was improved by 48% [1]
- Tumor metastasis suppression: In C57BL/6 mice bearing B16F10 melanoma lung metastasis model, L-Norleucine (500 mg/kg, oral gavage) for 14 days reduced the number of lung metastatic nodules by 67% compared to vehicle control; in BALB/c nude mice with MDA-MB-231 breast cancer lung metastasis, it decreased metastatic nodules by 59% [2]
- L-Norleucine did not affect primary tumor growth in both models, confirming its specific effect on metastasis rather than tumor proliferation [2]
Enzyme Assay
- Muscle protein synthesis assay: Isolated rat skeletal muscle strips were incubated in medium containing L-Norleucine (5-20 mM) and 3H-leucine for 2 hours at 37°C; muscle tissues were homogenized, proteins were precipitated with trichloroacetic acid, and radioactivity was measured by liquid scintillation counting to quantify 3H-leucine incorporation (index of protein synthesis) [1]
- Muscle protein degradation assay: Pre-labeled rat skeletal muscle strips (incubated with 3H-leucine for 24 hours) were treated with L-Norleucine (5-20 mM) for 4 hours; the radioactivity of 3H-leucine released into the medium was measured to evaluate protein degradation rate [1]
Cell Assay
- Tumor cell migration assay: MDA-MB-231 or B16F10 cells were seeded in the upper chamber of transwell inserts, and L-Norleucine (1-10 mM) was added to both upper and lower chambers; after 24 hours of incubation, cells that migrated to the lower chamber were fixed, stained, and counted under a microscope [2]
- Tumor cell invasion assay: Matrigel-coated transwell inserts were used; cells were seeded in the upper chamber with L-Norleucine (1-10 mM), and after 48 hours, invasive cells on the lower membrane were stained and quantified [2]
- Cell viability assay: Tumor cells were seeded in 96-well plates, treated with L-Norleucine (0.1-10 mM) for 48 hours, and cell viability was measured by MTT assay to exclude cytotoxic effects [2]
Animal Protocol
- Skeletal muscle protein turnover model: Male Wistar rats (200-250 g) were fasted for 12 hours, then randomly divided into control and treatment groups; the treatment group received L-Norleucine (1 g/kg) via intraperitoneal injection, and the control group received equal volume of saline; 2 hours after administration, rats were euthanized, and gastrocnemius muscle was isolated for protein synthesis and degradation rate analysis [1]
- Melanoma lung metastasis model: C57BL/6 mice (6-8 weeks old) were injected with B16F10 cells (1×10⁶ cells/mouse) via tail vein; 24 hours later, mice were treated with L-Norleucine (500 mg/kg) or vehicle via oral gavage once daily for 14 days; mice were euthanized, lungs were excised, and metastatic nodules were counted under a dissecting microscope [2]
- Breast cancer lung metastasis model: BALB/c nude mice (6-8 weeks old) were injected with MDA-MB-231 cells (2×10⁶ cells/mouse) via tail vein; L-Norleucine (500 mg/kg) or vehicle was administered by oral gavage once daily for 21 days; lungs were collected, and metastatic nodules were quantified [2]
References

[1]. On the role of branched-chain amino acids in protein turnover of skeletal muscle. Studies in vivo with L-norleucine. Z Naturforsch C. 1985 May-Jun;40(5-6):427-37.

[2]. The homeostasis-maintaining metabolites from bacterial stress response to bacteriophage infection suppress tumor metastasis. Oncogene. 2018 Jun 20.

Additional Infomation
L-Leucine is a non-protein L-α-amino acid composed of hexanoic acid with an amino group attached at the C-2 position. It is not naturally occurring. It is a 2-aminohexanoic acid, also a non-protein L-α-amino acid. It is the conjugate acid of L-2-aminohexanoic acid. It is the enantiomer of D-leucine. It is the zwitterion tautomer of L-2-aminohexanoic acid. Leucine is currently being studied in the clinical trial NCT00081952 (Amino Acid Therapy for Hot Flashes in Postmenopausal Women). L-Leucine has been reported to exist in Daphnia pulex, Arabidopsis thaliana, and other organisms with relevant data. Leucine is a non-natural amino acid commonly used in experimental studies of protein structure and function. The structure of L-leucine is similar to methionine, but it does not contain sulfur.
- L-leucine is a non-protein amino acid and a structural analog of branched-chain amino acids (leucine, isoleucine, valine)[1][2]
- Its mechanism of action in skeletal muscle is to compete with endogenous branched-chain amino acids for transport and metabolism, thereby stimulating protein synthesis and inhibiting proteolysis[1]
- As a metabolite of bacteria infected by bacteriophages, L-leucine inhibits tumor metastasis by regulating the metastatic phenotype (migration, invasion) of tumor cells without affecting cell proliferation[2]
- L-leucine is highly selective for metastasis and skeletal muscle protein metabolism, and no cytotoxicity to normal cells or tumor cells has been observed at effective concentrations[1][2]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H13NO2
Molecular Weight
131.17292
Exact Mass
131.094
CAS #
327-57-1
Related CAS #
L-Norleucine-d9;1331889-36-1
PubChem CID
21236
Appearance
White to off-white solid powder
Density
1.0±0.1 g/cm3
Boiling Point
234.0±23.0 °C at 760 mmHg
Melting Point
300ºC
Flash Point
95.3±22.6 °C
Vapour Pressure
0.0±1.0 mmHg at 25°C
Index of Refraction
1.465
LogP
0.92
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
4
Heavy Atom Count
9
Complexity
93.1
Defined Atom Stereocenter Count
1
SMILES
CCCC[C@@H](C(=O)O)N
InChi Key
LRQKBLKVPFOOQJ-YFKPBYRVSA-N
InChi Code
InChI=1S/C6H13NO2/c1-2-3-4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m0/s1
Chemical Name
(2S)-2-aminohexanoic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~5 mg/mL (~38.12 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 2.86 mg/mL (21.80 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C).

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 7.6237 mL 38.1185 mL 76.2369 mL
5 mM 1.5247 mL 7.6237 mL 15.2474 mL
10 mM 0.7624 mL 3.8118 mL 7.6237 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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