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H-D-Leu-OH

Alias: (R)-Leucine; D-Leucine; H-D-Leu-OH
Cat No.:V37191 Purity: ≥98%
D-Leucine has anti-epileptic activity, which is more active than L-leucine.
H-D-Leu-OH
H-D-Leu-OH Chemical Structure CAS No.: 328-38-1
Product category: Amino Acids
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of H-D-Leu-OH:

  • D-Leucine-d10-Leucine-d10)
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
D-Leucine has anti-epileptic activity, which is more active than L-leucine. D-leucine effectively terminates epileptic seizures. In vitro, D-Leucine can reduce long-term sites but has no effect on basal synaptic transmission.
H-D-Leu-OH, also known as D-Leucine, is the D-enantiomer of the essential branched-chain amino acid L-leucine. It is a non-proteinogenic amino acid that is a metabolite of Saccharomyces cerevisiae and a marker in the diagnosis of maple syrup urine disease. It has a molecular weight of 131.18 g/mol and formula C6H13NO2. It appears as a white to off-white solid with a melting point >300°C.
Biological Activity I Assay Protocols (From Reference)
Targets
Human Endogenous Metabolite
H-D-Leu-OH is classified as a D-α-amino acid belonging to the leucine family. It does not have a specific biological receptor target. Its primary application is as a specialized chiral building block in peptide synthesis for introducing D-leucine residues. The D-configuration provides stereochemical control for producing single-stereoisomer peptides with enhanced proteolytic stability. It is also used as an internal standard.
ln Vitro
D-leucine did not compete with cognate ligand binding in a screen of potential neural receptors, which would indicate a different target. D-leucine suppresses continuing seizures at least as well as diazepam, even at modest doses. According to these results, D-leucine might be a member of a novel class of antiepileptic medications and might have uses in eukaryotes that have not been discovered before [1].
In vitro activity for H-D-Leu-OH is primarily as a peptide synthesis reagent. Amino acids and amino acid derivatives have been commercially used as ergogenic supplements. They influence the secretion of anabolic hormones, supply of fuel during exercise, mental performance during stress-related tasks and prevent exercise-induced muscle damage. H-D-Leu-OH itself is not directly biologically active; its utility is in preparing D-leucine-containing peptides for subsequent biological evaluation.
ln Vivo
In vivo activity data for H-D-Leu-OH as a standalone compound is not applicable. It is a non-proteinogenic D-amino acid used exclusively as a research building block and is not intended for direct in vivo administration. Peptides synthesized using this building block may be evaluated in animal models for various biological activities. The D-configuration can confer proteolytic resistance to peptides.
Enzyme Assay
In vitro enzyme/receptor binding protocols for H-D-Leu-OH involve studying its interactions with enzymes involved in branched-chain amino acid metabolism. The compound can be used in receptor binding studies to investigate the effects of D-configuration on ligand-receptor interactions. For enzyme activity studies, H-D-Leu-OH can be used as a substrate or inhibitor to probe enzyme specificity.
Cell Assay
Cell culture protocols for H-D-Leu-OH involve dissolving the compound in sterile water or cell culture medium. Cells are treated with concentrations ranging from 0.1-100 µM for 24-72 hours. Effects on cell viability, proliferation, and metabolism are assessed. The compound can be used to study amino acid transport and metabolism in cell models.
Animal Protocol
In vivo animal study protocols for H-D-Leu-OH involve administration via oral gavage or injection in saline. Dosing typically ranges from 10-100 mg/kg depending on the study. Studies may assess effects on protein metabolism and amino acid homeostasis. Blood and tissue samples are collected for analysis of compound distribution and metabolite levels.
ADME/Pharmacokinetics
Pharmacokinetic properties of H-D-Leu-OH are characteristic of small amino acids. The compound has a molecular weight of 131.18 g/mol, formula C6H13NO2, and CAS number 328-38-1. Melting point is >300°C. Density is 1.119 g/cm3. Storage is recommended at room temperature in a cool, dark place below 15°C.
Toxicity/Toxicokinetics
Limited toxicological data is available for H-D-Leu-OH. The compound is for research use only and is not intended for human therapeutic use. Standard safety precautions for handling amino acids should be observed. No specific toxicity studies have been reported.
References

[1]. Combination of PARP Inhibitor and Temozolomide to Suppress Chordoma Progression. J Mol Med (Berl). 2019 Aug;97(8):1183-1193.

Additional Infomation
D-Leucine is the D-enantiomer of leucine. It is a bacterial metabolite, specifically a metabolite of Saccharomyces cerevisiae. It is a leucine and a D-α-amino acid. It is the conjugate base of D-leucine ononium and the conjugate acid of D-leucine acid. It is an enantiomer of L-leucine and a zwitterion tautomer of D-leucine. D-leucine has been reported to exist in Saccharomyces cerevisiae, and relevant data are available for reference.
H-D-Leu-OH (CAS#: 328-38-1) is also known as D-Leucine, (R)-2-Amino-4-methylpentanoic acid, and D-2-Amino-4-methylvaleric acid. Its molecular formula is C6H13NO2. It is a non-proteinogenic D-amino acid used as a chiral building block in peptide synthesis and as an internal standard. It has no approved therapeutic indications.
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 #
328-38-1
Related CAS #
D-Leucine-d10; 271247-12-2
PubChem CID
439524
Appearance
White to off-white powder
Density
1.0±0.1 g/cm3
Boiling Point
225.8±23.0 °C at 760 mmHg
Melting Point
> 300ºC
Flash Point
90.3±22.6 °C
Vapour Pressure
0.0±0.9 mmHg at 25°C
Index of Refraction
1.463
LogP
0.73
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
3
Heavy Atom Count
9
Complexity
101
Defined Atom Stereocenter Count
1
SMILES
N[C@H](CC(C)C)C(O)=O
InChi Key
ROHFNLRQFUQHCH-RXMQYKEDSA-N
InChi Code
InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m1/s1
Chemical Name
(2R)-2-amino-4-methylpentanoic acid
Synonyms
(R)-Leucine; D-Leucine; H-D-Leu-OH
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 : ~10 mg/mL (~76.24 mM)
DMSO :< 1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: 2 mg/mL (15.25 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.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

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.
             (2) Be sure to add the solvent(s) in order.

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