L-Norvaline
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MedKoo CAT#: 464799

CAS#: 6600-40-4

Description: L-Norvaline is a non-proteinogenic amino acid, an isomer of valine, and an inhibitor of arginase and p70 ribosomal S6 kinase 1 (p70S6K1) kinase. It inhibits arginase-mediated urea production in J774A. macrophage lysates when used at a concentration of 10 mM and TNF-α-induced p70S6K1 activation in human umbilical vein endothelial cells (HUVECs) at 20 mM.1 L-Norvaline reduces microgliosis and the level of amyloid-β fibrils in the hippocampus, as well as improves learning and memory in the Morris water maze in the 3xTg mouse model of Alzheimer’s disease.

Chemical Structure

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L-Norvaline
CAS# 6600-40-4
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 464799
Name: L-Norvaline
CAS#: 6600-40-4
Chemical Formula: C5H11NO2
Exact Mass: 117.08
Molecular Weight: 117.148
Elemental Analysis: C, 51.26; H, 9.46; N, 11.96; O, 27.31

Price and Availability

Size Price Availability Quantity
5g USD 250 2 Weeks
25g USD 450 2 Weeks
100g USD 850 2 Weeks
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Synonym: L-Norvaline; L Norvaline; α-L-Aminopentanoic Acid; L-Nva; LNva; L Nva; NSC 203786; NSC203786; NSC-203786;

IUPAC/Chemical Name: (S)-2-aminopentanoic acid

InChi Key: SNDPXSYFESPGGJ-BYPYZUCNSA-N

InChi Code: InChI=1S/C5H11NO2/c1-2-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1

SMILES Code: CCC[C@@H](C(O)=O)N

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: L-Norvaline is an endogenous metabolite.
In vitro activity: The induction of the expression of endothelial VCAM-1, ICAM-1 and E-selectin by TNFalpha was concentration-dependently reduced by incubation of the endothelial cells with the arginase inhibitor L-norvaline. Moreover, the inhibitory effect of L-norvaline was not reversed by the NOS inhibitor L-NAME and L-norvaline did not interfere with TNFalpha-induced activation of NF-kappaB, JNK, p38mapk, while it inhibited p70s6k (S6K1) activity. Reference: BMC Cardiovasc Disord. 2009 Mar 13;9:12. https://pubmed.ncbi.nlm.nih.gov/19284655/
In vivo activity: L-norvaline (250 mg/L), for 2.5 months to a triple-transgenic model (3×Tg-AD (Alzheimer’s disease)) harboring PS1M146V, APPSwe, and tauP301L transgenes. Remarkably, L-norvaline treatment reverses the cognitive decline in AD mice. Moreover, elevated levels of neuroplasticity related postsynaptic density protein 95 were detected in the hippocampi of mice treated with L-norvaline. Reference: Neural Regen Res. 2019 Sep;14(9):1562-1572. https://pubmed.ncbi.nlm.nih.gov/31089055/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
PBS (pH 7.2) 10.0 85.36

Preparing Stock Solutions

The following data is based on the product molecular weight 117.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Ming XF, Rajapakse AG, Carvas JM, Ruffieux J, Yang Z. Inhibition of S6K1 accounts partially for the anti-inflammatory effects of the arginase inhibitor L-norvaline. BMC Cardiovasc Disord. 2009 Mar 13;9:12. doi: 10.1186/1471-2261-9-12. PMID: 19284655; PMCID: PMC2664787. 2. Polis B, Srikanth KD, Gurevich V, Gil-Henn H, Samson AO. L-Norvaline, a new therapeutic agent against Alzheimer's disease. Neural Regen Res. 2019 Sep;14(9):1562-1572. doi: 10.4103/1673-5374.255980. PMID: 31089055; PMCID: PMC6557086. 3. Polis B, Srikanth KD, Elliott E, Gil-Henn H, Samson AO. L-Norvaline Reverses Cognitive Decline and Synaptic Loss in a Murine Model of Alzheimer's Disease. Neurotherapeutics. 2018 Oct;15(4):1036-1054. doi: 10.1007/s13311-018-0669-5. PMID: 30288668; PMCID: PMC6277292.
In vitro protocol: 1. Ming XF, Rajapakse AG, Carvas JM, Ruffieux J, Yang Z. Inhibition of S6K1 accounts partially for the anti-inflammatory effects of the arginase inhibitor L-norvaline. BMC Cardiovasc Disord. 2009 Mar 13;9:12. doi: 10.1186/1471-2261-9-12. PMID: 19284655; PMCID: PMC2664787.
In vivo protocol: 1. Polis B, Srikanth KD, Gurevich V, Gil-Henn H, Samson AO. L-Norvaline, a new therapeutic agent against Alzheimer's disease. Neural Regen Res. 2019 Sep;14(9):1562-1572. doi: 10.4103/1673-5374.255980. PMID: 31089055; PMCID: PMC6557086. 2. Polis B, Srikanth KD, Elliott E, Gil-Henn H, Samson AO. L-Norvaline Reverses Cognitive Decline and Synaptic Loss in a Murine Model of Alzheimer's Disease. Neurotherapeutics. 2018 Oct;15(4):1036-1054. doi: 10.1007/s13311-018-0669-5. PMID: 30288668; PMCID: PMC6277292.

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1: Homa J, Klosowska A, Chadzinska M. Arginase Activity in Eisenia andrei Coelomocytes: Function in the Earthworm Innate Response. Int J Mol Sci. 2021 Apr 1;22(7):3687. doi: 10.3390/ijms22073687. PMID: 33916228; PMCID: PMC8037997.

2: Sun C, Jiang Y, Cui M, Qiao L, Wei J, Huang Y, Zhang L, He T, Li S, Hsu HY, Qin C, Long R, Yuan M. High-performance large-area quasi-2D perovskite light- emitting diodes. Nat Commun. 2021 Apr 13;12(1):2207. doi: 10.1038/s41467-021-22529-x. PMID: 33850141; PMCID: PMC8044177.

3: Ren X, Wang N, Zhou Y, Song A, Jin G, Li Z, Luan Y. An injectable hydrogel using an immunomodulating gelator for amplified tumor immunotherapy by blocking the arginase pathway. Acta Biomater. 2021 Apr 1;124:179-190. doi: 10.1016/j.actbio.2021.01.041. Epub 2021 Jan 30. PMID: 33524560.

4: Levina AD, Mikhailova ES, Kasumyan AO. Taste preferences and feeding behaviour in the facultative herbivorous fish, Nile tilapia Oreochromis niloticus. J Fish Biol. 2021 May;98(5):1385-1400. doi: 10.1111/jfb.14675. Epub 2021 Feb 2. PMID: 33448377.

5: Macri AM, Lam S, Powers RH, Marsico ALM. Differentiation of Morphologically Similar Human Head Hairs from Two Demographically Similar Individuals Using Amino Acid Ratios. J Forensic Sci. 2020 Sep;65(5):1745-1751. doi: 10.1111/1556-4029.14489. Epub 2020 Jul 20. PMID: 33104306.

6: Domvri K, Petanidis S, Anestakis D, Porpodis K, Bai C, Zarogoulidis P, Freitag L, Hohenforst-Schmidt W, Katopodi T. Dual photothermal MDSCs-targeted immunotherapy inhibits lung immunosuppressive metastasis by enhancing T-cell recruitment. Nanoscale. 2020 Apr 3;12(13):7051-7062. doi: 10.1039/d0nr00080a. PMID: 32186564.

7: Gilinsky MA, Polityko YK, Markel AL, Latysheva TV, Samson AO, Polis B, Naumenko SE. Norvaline Reduces Blood Pressure and Induces Diuresis in Rats with Inherited Stress-Induced Arterial Hypertension. Biomed Res Int. 2020 Feb 12;2020:4935386. doi: 10.1155/2020/4935386. PMID: 32149110; PMCID: PMC7042509.

8: Xu D, Sánchez-López E, Wang Q, Jiang Z, Marina ML. Determination of l-norvaline and l-tryptophan in dietary supplements by nano-LC using an O-[2-(methacryloyloxy)-ethylcarbamoyl]-10,11-dihydroquinidine-silica hybrid monolithic column. J Pharm Anal. 2020 Feb;10(1):70-77. doi: 10.1016/j.jpha.2019.10.001. Epub 2019 Oct 23. PMID: 32123601; PMCID: PMC7037541.

9: Polis B, Gilinsky MA, Samson AO. Reports of L-Norvaline Toxicity in Humans May Be Greatly Overstated. Brain Sci. 2019 Dec 17;9(12):382. doi: 10.3390/brainsci9120382. PMID: 31861122; PMCID: PMC6955955.

10: Polis B, Gurevich V, Assa M, Samson AO. Norvaline Restores the BBB Integrity in a Mouse Model of Alzheimer's Disease. Int J Mol Sci. 2019 Sep 18;20(18):4616. doi: 10.3390/ijms20184616. PMID: 31540372; PMCID: PMC6770953.

11: Sorbara NT, MacMillan JWM, McCluskey GD, Bearne SL. Substrate-product analogue inhibitors of isoleucine 2-epimerase from Lactobacillus buchneri by rational design. Org Biomol Chem. 2019 Sep 25;17(37):8618-8627. doi: 10.1039/c9ob01823a. PMID: 31528932.

12: Zheng X, Cui Y, Li T, Li R, Guo L, Li D, Wu B. Biochemical and structural characterization of a highly active branched-chain amino acid aminotransferase from Pseudomonas sp. for efficient biosynthesis of chiral amino acids. Appl Microbiol Biotechnol. 2019 Oct;103(19):8051-8062. doi: 10.1007/s00253-019-10105-9. Epub 2019 Sep 4. PMID: 31485690.

13: Malik A, Dalal V, Ankri S, Tomar S. Structural insights into Entamoeba histolytica arginase and structure-based identification of novel non- amino acid based inhibitors as potential antiamoebic molecules. FEBS J. 2019 Oct;286(20):4135-4155. doi: 10.1111/febs.14960. Epub 2019 Jul 17. PMID: 31199070.

14: Muchaamba F, Eshwar AK, Stevens MJA, von Ah U, Tasara T. Variable Carbon Source Utilization, Stress Resistance, and Virulence Profiles Among Listeria monocytogenes Strains Responsible for Listeriosis Outbreaks in Switzerland. Front Microbiol. 2019 May 3;10:957. doi: 10.3389/fmicb.2019.00957. PMID: 31130938; PMCID: PMC6510287.

15: Polis B, Srikanth KD, Gurevich V, Gil-Henn H, Samson AO. L-Norvaline, a new therapeutic agent against Alzheimer's disease. Neural Regen Res. 2019 Sep;14(9):1562-1572. doi: 10.4103/1673-5374.255980. PMID: 31089055; PMCID: PMC6557086.

16: Gao L, Zhang JH, Chen XX, Ren HL, Feng XL, Wang JL, Xiao JH. Combination of L-Arginine and L-Norvaline protects against pulmonary fibrosis progression induced by bleomycin in mice. Biomed Pharmacother. 2019 May;113:108768. doi: 10.1016/j.biopha.2019.108768. Epub 2019 Mar 17. PMID: 30889486.

17: Samardzic K, Rodgers KJ. Cytotoxicity and mitochondrial dysfunction caused by the dietary supplement l-norvaline. Toxicol In Vitro. 2019 Apr;56:163-171. doi: 10.1016/j.tiv.2019.01.020. Epub 2019 Jan 29. PMID: 30703532.

18: Sobolev MS, Faitelson AV, Gudyrev OS, Rajkumar DSR, Dubrovin GM, Anikanov AV, Koklina NU, Chernomortseva ES. Study of Endothelio- and Osteoprotective Effects of Combination of Rosuvastatin with L-Norvaline in Experiment. J Osteoporos. 2018 Nov 5;2018:1585749. doi: 10.1155/2018/1585749. PMID: 30519391; PMCID: PMC6241240.

19: Polis B, Srikanth KD, Elliott E, Gil-Henn H, Samson AO. L-Norvaline Reverses Cognitive Decline and Synaptic Loss in a Murine Model of Alzheimer's Disease. Neurotherapeutics. 2018 Oct;15(4):1036-1054. doi: 10.1007/s13311-018-0669-5. PMID: 30288668; PMCID: PMC6277292.

20: Ovsepian SV, O'Leary VB. Can Arginase Inhibitors Be the Answer to Therapeutic Challenges in Alzheimer's Disease? Neurotherapeutics. 2018 Oct;15(4):1032-1035. doi: 10.1007/s13311-018-0668-6. PMID: 30242774; PMCID: PMC6277284.