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H-DL-Lys-OH·HCl

Cat No.:V36186 Purity: ≥98%
H-Lys(Z)-OMe.HCl is a lysine analogue.
H-DL-Lys-OH·HCl
H-DL-Lys-OH·HCl Chemical Structure CAS No.: 27894-50-4
Product category: Peptides
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
H-Lys(Z)-OMe.HCl is a lysine analogue.
H-DL-Lys-OH·HCl (CAS# 27894-50-4) is a racemic mixture of the lysine amino acid in its hydrochloride salt form, commonly utilized as a biochemical reagent and research tool. As a lysine analogue, it serves as a fundamental building block in peptide synthesis and cell culture media formulations. This compound is primarily used in laboratory settings for studying amino acid metabolism, protein synthesis, and as a reference standard in analytical chemistry. The racemic nature of this product makes it valuable for studies investigating stereoselectivity in biological systems. It is not an approved pharmaceutical drug but rather a research-grade chemical.
Biological Activity I Assay Protocols (From Reference)
Targets
As a basic amino acid derivative, H-DL-Lys-OH·HCl does not have a specific defined pharmacological target in the classical sense of drug-receptor interactions. In biological systems, lysine and its analogues interact with amino acid transporters, including the cationic amino acid transporter (CAT) family and system y⁺ transporters, which mediate cellular uptake of basic amino acids. Additionally, lysine derivatives may interact with enzymes involved in amino acid metabolism, such as lysine decarboxylase and lysine oxidase. In cell culture applications, this compound serves as a nutrient source supplying essential amino acids for cellular protein synthesis and metabolic pathways.
ln Vitro
Commercial ergot supplements have been made from amino acids and their derivatives. They affect the release of anabolic hormones, the availability of fuel for activity, the ability to think clearly under pressure, and the prevention of muscular damage brought on by exertion. They are regarded as advantageous synergistic food ingredients [1].
In vitro studies with lysine derivatives have demonstrated their effects on cellular metabolism and protein synthesis. Amino acid derivatives like H-DL-Lys-OH·HCl influence the release of anabolic hormones and affect the availability of fuel for cellular activity. Research indicates that lysine supplementation can enhance calcium absorption and reduce urinary calcium excretion in cell-based models. The compound has been shown to support cell viability and proliferation in various culture systems by providing essential nitrogen sources. Studies also suggest that lysine derivatives may play a role in preventing muscular damage induced by exertion through their effects on protein metabolism and tissue repair mechanisms.
ln Vivo
In vivo studies on lysine derivatives have focused primarily on their nutritional and metabolic effects rather than therapeutic applications. Animal studies have demonstrated that lysine supplementation can influence growth performance, nitrogen balance, and immune function. Research in rodent models has shown that lysine derivatives affect the release of anabolic hormones and the availability of fuel for physical activity. These compounds have been investigated for their potential to improve mental performance under stress and prevent exercise-induced muscle damage. However, H-DL-Lys-OH·HCl specifically has limited published in vivo data as it is primarily a research reagent rather than a drug candidate.
Enzyme Assay
Typical in vitro enzyme/receptor binding assays for amino acid derivatives involve radioligand binding or fluorescence-based competition assays. A standard protocol includes preparing a series of compound concentrations in assay buffer (e.g., PBS pH 7.4) and incubating with the target enzyme or receptor preparation. For amino acid transporters, assays often use radiolabeled substrates (e.g., ³H-lysine) to measure competitive displacement. After incubation at 37°C for 30-60 minutes, bound and free radioligand are separated by rapid filtration through glass fiber filters, followed by scintillation counting. IC₅₀ values are calculated from dose-response curves using nonlinear regression analysis.
Cell Assay
In vitro cellular assays for lysine derivatives typically employ cell lines such as HEK293, HeLa, or primary cell cultures. A common protocol involves seeding cells in 96-well plates at 5×10³ to 1×10⁴ cells per well in appropriate growth medium and incubating overnight at 37°C with 5% CO₂. Cells are then treated with varying concentrations of the compound (typically 0.1-1000 µM) for 24-72 hours. Cell viability is assessed using MTT or CCK-8 assays, where absorbance is measured at 570 nm or 450 nm respectively. Metabolic effects can be evaluated by measuring glucose consumption, lactate production, or amino acid uptake using commercial assay kits.
Animal Protocol
In vivo animal studies with lysine derivatives typically utilize rodent models such as Sprague-Dawley rats or C57BL/6 mice. A standard protocol involves oral gavage or intraperitoneal administration of the compound dissolved in sterile saline or PBS at doses ranging from 50-500 mg/kg body weight. Animals are maintained under standard laboratory conditions with ad libitum access to food and water. Blood samples are collected at predetermined time points (0, 1, 2, 4, 8, 24 hours) via tail vein or cardiac puncture. Tissue samples (liver, kidney, muscle, brain) may be harvested for analysis of amino acid concentrations, metabolic markers, and gene expression changes.
ADME/Pharmacokinetics
As a small amino acid derivative (molecular weight ~330.81 g/mol), H-DL-Lys-OH·HCl is expected to exhibit favorable oral bioavailability due to its small size and polar nature. The compound is highly soluble in aqueous solutions, facilitating absorption from the gastrointestinal tract. Following absorption, it distributes throughout bodily fluids and tissues via amino acid transport systems. The compound is primarily metabolized through transamination and decarboxylation pathways, with excretion occurring via renal filtration. The hydrochloride salt form enhances aqueous solubility and stability. Plasma half-life is typically short (1-3 hours) for amino acid derivatives due to rapid clearance.
Toxicity/Toxicokinetics
The hydrochloride salt of lysine exhibits low acute toxicity, consistent with its nature as a naturally occurring amino acid derivative. The oral LD₅₀ in rodents is expected to be >2000 mg/kg based on data from similar amino acid compounds. Common adverse effects at high doses may include gastrointestinal discomfort, nausea, and diarrhea due to osmotic effects. The compound is not considered genotoxic or carcinogenic. Skin and eye irritation potential is low, though standard laboratory precautions should be observed. The compound is stable under normal handling conditions and does not present significant environmental hazards.
References
[1]. Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144.
Additional Infomation
H-DL-Lys-OH·HCl is a research-grade chemical supplied as a white to off-white solid powder with a melting point of 115-118°C. The compound has a boiling point of 444.6°C at 760 mmHg and a flash point of 222.7°C. It should be stored as a powder at -20°C for up to 3 years or at 4°C for up to 2 years, and in solution at -80°C for 6 months or -20°C for 1 month. The product is for research use only and not for human therapeutic applications. It is not approved by any regulatory agency for clinical use and has no known marketed drug status.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H23CLN2O4
Molecular Weight
330.8071
Exact Mass
330.134
CAS #
27894-50-4
PubChem CID
12935371
Appearance
White to off-white solid powder
Boiling Point
444.6ºC at 760mmHg
Melting Point
115-118°C
Flash Point
222.7ºC
Vapour Pressure
4.23E-08mmHg at 25°C
Index of Refraction
1.524
LogP
3.476
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
10
Heavy Atom Count
22
Complexity
317
Defined Atom Stereocenter Count
1
SMILES
Cl[H].O(C([H])([H])[H])C([C@]([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=O)OC([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H])N([H])[H])=O
InChi Key
QPNJISLOYQGQTI-ZOWNYOTGSA-N
InChi Code
InChI=1S/C15H22N2O4.ClH/c1-20-14(18)13(16)9-5-6-10-17-15(19)21-11-12-7-3-2-4-8-12;/h2-4,7-8,13H,5-6,9-11,16H2,1H3,(H,17,19);1H/t13-;/m0./s1
Chemical Name
methyl (2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoate;hydrochloride
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

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.0229 mL 15.1144 mL 30.2288 mL
5 mM 0.6046 mL 3.0229 mL 6.0458 mL
10 mM 0.3023 mL 1.5114 mL 3.0229 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

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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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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  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • 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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  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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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
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • The answer appears in the Volume (to add to vial) box
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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