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N-Carbobenzoxy-L-homoserine (N-(Benzyloxycarbonyl)-L-homoserine)

N-Carbobenzoxy-L-homoserine (N-(Benzyloxycarbonyl)-L-homoserine)
N-Carbobenzoxy-L-homoserine (N-(Benzyloxycarbonyl)-L-homoserine) Chemical Structure CAS No.: 35677-88-4
Product category: Others 14
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
N-Carbobenzoxy-L-homoserine (N-(Benzyloxycarbonyl)-L-homoserine) is L-homoserine with an N-Carbobenzoxy protecting group and can be used as a linker (ADC Linker) in the synthesis of Antibody-Drug Conjugates (ADCs).
N-Carbobenzoxy-L-homoserine (N-(Benzyloxycarbonyl)-L-homoserine, CAS# 35677-88-4) is an L-homoserine derivative bearing an N-carbobenzoxy (Cbz, Z) protecting group. This compound is a protected amino acid used as a building block in peptide synthesis. The Cbz group is a common amine-protecting group that can be removed by catalytic hydrogenation. It is also utilized as a linker (ADC Linker) in the synthesis of antibody-drug conjugates (ADCs). It serves as a precursor for more complex molecules and is a valuable tool in organic and medicinal chemistry. It is intended for research use only and is not a therapeutic agent.
Biological Activity I Assay Protocols (From Reference)
Targets
N-Carbobenzoxy-L-homoserine does not have a direct biological target as it is a protected amino acid used as a chemical building block rather than a pharmacologically active compound. Its function is to serve as a synthetic precursor in peptide and ADC synthesis. The Cbz group protects the amine functionality during chemical reactions, allowing for selective modifications elsewhere in the molecule. Once the Cbz group is removed, the free amine can participate in peptide bond formation. It is not designed to interact with biological receptors or enzymes.
ln Vitro
N-Carbobenzoxy-L-homoserine is a chemical intermediate and does not possess direct in vitro biological activity against any specific target. Its utility is demonstrated in chemical synthesis rather than in biological assays. As a protected amino acid, it is used to synthesize peptides and other bioactive molecules. The compound's purity and identity are confirmed by standard analytical techniques. Its physical properties, such as solubility in DMSO, are documented for handling in synthesis. It serves as a precursor for compounds that would subsequently be evaluated for biological activity.
ln Vivo
N-Carbobenzoxy-L-homoserine is not a pharmacologically active compound and does not have direct in vivo activity. Its role is confined to chemical synthesis as a building block or ADC linker. Any in vivo effects would be attributed to the final drug substance synthesized from this intermediate. The compound itself is not administered to animals for efficacy studies. It is stored and handled based on its chemical properties to maintain stability for use in organic synthesis. It is not intended for biological evaluation in living organisms.
Enzyme Assay
Standard in vitro enzyme/receptor binding assays are not applicable to N-Carbobenzoxy-L-homoserine as it is a synthetic intermediate without biological activity. Quality control for this compound relies on analytical chemistry techniques. High-Performance Liquid Chromatography (HPLC) is used to assess purity. Nuclear Magnetic Resonance (NMR) spectroscopy confirms the correct structure and stereochemistry. Solubility testing in solvents such as DMSO is performed to guide its handling in chemical reactions. No receptor binding or enzymatic activity assays are performed on this intermediate.
Cell Assay
Cell-based assays are not performed on N-Carbobenzoxy-L-homoserine as it is not a biologically active compound. It is a chemical reagent used in the laboratory for peptide and ADC synthesis. Its evaluation is limited to chemical purity, identity, and stability. In the context of ADC synthesis, it may be conjugated to other molecules, and the resulting ADC would be tested in cell-based assays. However, the intermediate itself is not subjected to cell culture experiments for efficacy or toxicity. Handling procedures are based on its chemical properties.
Animal Protocol
In vivo animal experiments are not conducted with N-Carbobenzoxy-L-homoserine. This compound is exclusively a synthetic building block used in chemical synthesis. Once a final drug candidate is synthesized from this intermediate, it may be subjected to in vivo studies in animal models. However, the intermediate itself is not administered to animals. All pharmacological evaluation is deferred to the final compound derived from this building block. It is not intended for direct biological administration.
ADME/Pharmacokinetics
Pharmacokinetic properties are not applicable to N-Carbobenzoxy-L-homoserine as it is a synthetic reagent, not a therapeutic agent. The compound is a white to off-white solid powder. It is recommended to be stored as a powder at -20°C for up to three years and at 4°C for up to two years. In solvent, it is stable at -80°C for six months and at -20°C for one month. It is typically soluble in DMSO. These properties are characterized to facilitate its use in chemical synthesis.
Toxicity/Toxicokinetics
Toxicological data for N-Carbobenzoxy-L-homoserine are not available as it is a research chemical intermediate. Standard laboratory safety precautions for handling chemical reagents should be followed, including the use of personal protective equipment and working in a fume hood. The compound is not intended for human or animal consumption. Its specific toxicity profile has not been established. Any toxicological assessment would be performed on the final drug candidate, not on this synthetic precursor.
Additional Infomation
N-Carbobenzoxy-L-homoserine is a protected amino acid used in peptide synthesis and as an ADC linker. Its molecular formula is C12H15NO5, and its molecular weight is 253.25. It is also known as Cbz-L-homoserine or N-CBZ-L-homoserine. The compound has a melting point of 100-101°C. It is a useful compound in organic synthesis. It is commercially available from various suppliers for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H15NO5
Molecular Weight
253.25
Exact Mass
253.095
CAS #
35677-88-4
PubChem CID
489187
Appearance
White to off-white solid powder
Density
1.3±0.1 g/cm3
Boiling Point
519.9±50.0 °C at 760 mmHg
Melting Point
100-101ºC
Flash Point
268.2±30.1 °C
Vapour Pressure
0.0±1.4 mmHg at 25°C
Index of Refraction
1.564
LogP
1.3
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
7
Heavy Atom Count
18
Complexity
276
Defined Atom Stereocenter Count
1
SMILES
O(C([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H])C(N([H])[C@]([H])(C(=O)O[H])C([H])([H])C([H])([H])O[H])=O
InChi Key
UBXPAGGJJMSWLC-JTQLQIEISA-N
InChi Code
InChI=1S/C12H15NO5/c14-7-6-10(11(15)16)13-12(17)18-8-9-4-2-1-3-5-9/h1-5,10,14H,6-8H2,(H,13,17)(H,15,16)/t10-/m0/s1
Chemical Name
(2S)-4-hydroxy-2-(phenylmethoxycarbonylamino)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)
Typically soluble in DMSO (e.g. 10 mM)
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 3.9487 mL 19.7433 mL 39.4867 mL
5 mM 0.7897 mL 3.9487 mL 7.8973 mL
10 mM 0.3949 mL 1.9743 mL 3.9487 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
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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)
  • Click the “Calculate” button
  • 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:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
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.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • 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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