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Boc-L-Homoserine

Boc-L-Homoserine is a serine analogue.
Boc-L-Homoserine
Boc-L-Homoserine Chemical Structure CAS No.: 41088-86-2
Product category: Amino Acid Derivatives
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
25g
100g
Other Sizes
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Product Description
Boc-L-Homoserine is a serine analogue.
Boc-L-Homoserine (CAS 41088-86-2), also known as N-Boc-L-homoserine or (S)-2-(Boc-amino)-4-hydroxybutanoic acid, is a homoserine derivative featuring a tert-butyloxycarbonyl (Boc) protecting group on the amino functionality. It has a molecular formula of C₉H₁₇NO₅ and a molecular weight of 219.24 g/mol. Homoserine is a non-proteinogenic amino acid that is a homolog of serine, with an additional methylene group in the side chain. The compound is a protected amino acid derivative commonly utilized in peptide synthesis and protein engineering. The Boc protecting group allows for selective deprotection under acidic conditions, which is a key feature in Boc-based SPPS. The product is for research use only and not for human therapeutic applications.
Biological Activity I Assay Protocols (From Reference)
Targets
As an amino acid derivative, Boc-L-Homoserine does not have a defined primary drug target in the context of therapeutic development. However, as a protected homoserine analogue, it may be used in research to study amino acid metabolism, enzyme-substrate interactions, and peptide conformation. Homoserine is a non-proteinogenic amino acid that is a homolog of serine and an intermediate in the biosynthesis of threonine, methionine, and lysine in microorganisms. The Boc protecting group allows for selective deprotection under acidic conditions, which is a key feature in Boc-based SPPS. The compound can serve as a building block for synthesizing homoserine-containing peptides for studying protein structure and function.
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 on amino acid derivatives, including this homoserine analogue, have demonstrated their capacity to influence the release of anabolic hormones, modulate fuel availability for cellular activity, enhance mental performance under stress-related conditions, and prevent exercise-induced muscle damage. As a homoserine derivative, this compound may be used in cell-based assays to investigate amino acid transport mechanisms, protein synthesis, and the effects of amino acid supplementation on cellular metabolism. The compound can also be utilized in studies examining the role of homoserine in microbial metabolism and as a precursor for other amino acids.
ln Vivo
In vivo studies on amino acid derivatives have shown that 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. As a protected homoserine derivative, this compound may be administered in animal studies to evaluate the effects of homoserine supplementation or to study the pharmacokinetics and bioavailability of homoserine derivatives. However, specific in vivo pharmacological data for this exact compound remains limited, as it is primarily supplied as a research chemical for peptide synthesis rather than as a therapeutic agent.
Enzyme Assay
Non-cell-based enzyme or receptor binding assays for this compound typically involve enzymatic studies using purified enzymes involved in homoserine metabolism, such as homoserine dehydrogenase or homoserine kinase. Standard protocols include incubating varying concentrations of the test compound with the enzyme source in appropriate buffer systems, followed by measurement of enzymatic activity using spectrophotometric or chromatographic detection methods. For peptide synthesis applications, the compound is evaluated in coupling reactions using standard peptide synthesis chemistry to assess reactivity and coupling efficiency. The Boc protecting group allows for selective deprotection under acidic conditions (e.g., TFA).
Cell Assay
Cell-based assays for this homoserine derivative typically utilize mammalian cell lines or microbial cultures to evaluate compound uptake, cytotoxicity, and effects on cellular metabolism. Standard protocols involve culturing cells in appropriate media at 37°C in 5% CO₂, followed by treatment with varying concentrations of the compound (typically 0.1-100 μM) for 24-72 hours. Cell viability is assessed using MTT or CCK-8 assays. For microbial studies, the compound's effects on homoserine biosynthesis pathways can be investigated using auxotrophic strains. For peptide synthesis applications, the compound is used as a building block in Boc-based SPPS protocols.
Animal Protocol
In vivo animal studies for amino acid derivatives typically involve administration via oral gavage, intraperitoneal injection, or intravenous injection in rodent models (mice or rats). Standard protocols include dosing at ranges of 10-100 mg/kg body weight, with observations over 1-14 days depending on the study objectives. For studies evaluating the effects of homoserine on metabolism, animals may be administered the compound and monitored for changes in metabolic parameters or amino acid profiles. Pharmacodynamic assessments may include blood sampling for amino acid analysis, tissue collection for histopathological examination, and monitoring of body weight and general health parameters. All animal studies must comply with institutional ethical guidelines.
ADME/Pharmacokinetics
Pharmacokinetic properties for this Boc-protected homoserine derivative can be inferred from structurally related compounds. As a small molecule (molecular weight 219.24 g/mol) with moderate lipophilicity (LogP 0.7376), it is expected to have reasonable oral bioavailability. The Boc protecting group is likely to be cleaved in vivo to release the active homoserine. The compound shows moderate solubility in organic solvents and can be formulated for in vitro studies. For in vivo administration, formulations using suitable co-solvent systems may be employed. The compound should be stored at 4°C for long-term preservation. Definitive PK parameters such as half-life, Cmax, and AUC require formal studies.
Toxicity/Toxicokinetics
Toxicological data for this specific compound are limited as it is supplied for research use only and not intended for human therapeutic applications. Amino acid derivatives in general are considered to have low inherent toxicity based on their natural amino acid origins. However, as with all research chemicals, appropriate safety precautions should be observed during handling, including the use of personal protective equipment and work in well-ventilated areas. The compound may cause skin and eye irritation upon contact. Acute toxicity studies in animal models would be required to establish LD₅₀ values and no-observed-adverse-effect levels (NOAEL). For in vitro cytotoxicity assessment, the compound can be tested in mammalian cell lines using standard MTT or LDH release assays.
References

[1]. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144.

Additional Infomation
Boc-L-Homoserine is a protected homoserine derivative featuring a Boc protecting group on the amino functionality. Homoserine is a non-proteinogenic amino acid that is a homolog of serine and an intermediate in the biosynthesis of threonine, methionine, and lysine in microorganisms. This compound finds applications in the development of novel biosynthetic processes and bioactive compound synthesis through its role in modifying amino acid sequences. It is commonly utilized in peptide synthesis and protein engineering. The product is for research use only and not for human therapeutic applications. It is not an approved drug and has not undergone clinical trials.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C9H17NO5
Molecular Weight
219.23
Exact Mass
219.11
CAS #
41088-86-2
PubChem CID
13066457
Appearance
White to gray solid powder
Density
1.2±0.1 g/cm3
Boiling Point
421.6±40.0 °C at 760 mmHg
Melting Point
140°C(lit.)
Flash Point
208.8±27.3 °C
Vapour Pressure
0.0±2.3 mmHg at 25°C
Index of Refraction
1.485
LogP
0.69
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
6
Heavy Atom Count
15
Complexity
233
Defined Atom Stereocenter Count
1
SMILES
OCC[C@@H](C(O)=O)NC(OC(C)(C)C)=O
InChi Key
PZEMWPDUXBZKJN-LURJTMIESA-N
InChi Code
InChI=1S/C9H17NO5/c1-9(2,3)15-8(14)10-6(4-5-11)7(12)13/h6,11H,4-5H2,1-3H3,(H,10,14)(H,12,13)/t6-/m0/s1
Chemical Name
(2S)-4-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic 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)
DMSO: 50 mg/mL (228.07 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.40 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (11.40 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (11.40 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.5614 mL 22.8071 mL 45.6142 mL
5 mM 0.9123 mL 4.5614 mL 9.1228 mL
10 mM 0.4561 mL 2.2807 mL 4.5614 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:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
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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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • 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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • 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:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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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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