Alanine derivative
Z-Aib-OH targets peptide synthesis applications, particularly in solution-phase peptide synthesis. The α-aminoisobutyric acid (Aib) residue is highly sterically hindered and can induce helical conformations in peptides. The Z (benzyloxycarbonyl) group provides orthogonal protection for the amino group. It does not have a specific biological receptor target but is used in the synthesis of conformationally constrained peptides.

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 activity of Z-Aib-OH is primarily as a peptide synthesis reagent. Amino acid derivatives have been used as ergogenic supplements, affecting the release of anabolic hormones and fuel availability. Z-Aib-OH itself is not directly biologically active. Its utility is in preparing Aib-containing peptides for subsequent biological evaluation.

There is no specific in vivo activity data for Z-Aib-OH as a standalone compound. Peptides containing Aib residues synthesized using this building block may be evaluated in vivo for therapeutic applications. Aib residues can induce helical conformations and improve peptide stability. Animal studies would be performed on the final peptide products.

In vitro protocols for Z-Aib-OH involve its use in solution-phase peptide synthesis. The compound can be activated using coupling reagents and coupled to peptides in solution. The Z group is removed by hydrogenation or HBr in acetic acid. Purity is typically high. Melting point: not specified but compound is a solid powder. Storage: powder at -20°C for 3 years.

Cell-based protocols are not directly applicable to Z-Aib-OH as it is a synthesis building block. Aib-containing peptides synthesized using this reagent can be tested in cell culture. Peptides are dissolved in DMSO or appropriate buffers, sterile-filtered, and added to cells at concentrations of 0.1-100 µM. Incubation is typically 24-72 hours. Assays include cell viability, proliferation, and specific signaling readouts.

Animal studies with Z-Aib-OH are not conducted directly. Peptides containing Aib residues synthesized using this building block may be evaluated in vivo. Protocols involve administration of the peptide via appropriate routes in animal models. Pharmacokinetic sampling, efficacy assessment, and toxicological evaluation follow standard preclinical study designs. Aib residues can improve peptide stability and induce helical conformations.

Pharmacokinetic data for Z-Aib-OH as a standalone compound is not applicable. The compound has molecular weight 237.25 g/mol, formula C₁₂H₁₅NO₄, and appears as a powder. Density is 1.215 g/cm³. Boiling point is 423°C at 760 mmHg. Storage: powder at -20°C for 3 years. The Z group is removed by hydrogenation or acid treatment.

Toxicological data for Z-Aib-OH is limited. The compound is for research use only. Standard safety precautions should be observed. Acute toxicity is expected to be low. Store as powder at -20°C. Proper personal protective equipment should be worn when handling. No specific toxicity studies have been reported. It is not intended for human therapeutic use.

[1]. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1058.

Nutritional enhancers have long been used to improve athletic and competitive performance. A wide variety of dietary ingredients with enhancing effects are widely used by athletes. However, these ingredients are frequently subject to legal scrutiny due to their claimed benefits and safety concerns. Amino acid derivatives are widely touted as adjuvants that can effectively enhance physical and mental performance in multiple ways, but research suggests that individuals with amino acid deficiencies are more likely to benefit from amino acid derivative supplements than those with normal deficiencies. This article reviews some of the most common and widely used amino acid derivatives in sports and competitive sports, including creatine, tyrosine, carnitine, HMB, and taurine, and explores their effects on athletic performance, mental activity, and physical strength and composition. Creatine, carnitine, HMB, and taurine have been reported to delay the onset of fatigue and improve athletic performance and physical strength. HMB helps increase lean body mass and reduce exercise-induced muscle damage. Taurine has been found to reduce oxidative stress during exercise and has a blood pressure-lowering effect. While studies have not yet found any beneficial effects of tyrosine on athletic performance, it has been shown to effectively combat stress and improve mood and cognitive function, especially in individuals with sleep deprivation. Although published research data and results are still inconclusive regarding the efficacy of creatine, tyrosine, and HMB, more comprehensive research is needed on carnitine and taurine to provide a theoretical basis for their synergistic effects in nutritional adjustment and supplementation. [1]
Z-Aib-OH (CAS#: 15030-72-5) is also known as N-Benzyloxycarbonyl-α-aminoisobutyric acid, Z-α-methylalanine, and 2-methyl-2-(phenylmethoxycarbonylamino)propanoic acid. Its molecular formula is C₁₂H₁₅NO₄ and molecular weight is 237.25 g/mol. It is a sterically hindered amino acid used in solution-phase peptide synthesis. It has no approved therapeutic indications.

C12H15NO4

237.2518

103.063

15030-72-5

294936

White to off-white powder

1.2±0.1 g/cm3

204.4±23.0 °C at 760 mmHg

65-69ºC(lit.)

77.4±22.6 °C

0.1±0.8 mmHg at 25°C

1.540

-0.33

2

4

5

17

282

0

CC(C(O)=O)(NC(OCC1=CC=CC=C1)=O)C

QKVCSJBBYNYZNM-UHFFFAOYSA-N

InChI=1S/C12H15NO4/c1-12(2,10(14)15)13-11(16)17-8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3,(H,13,16)(H,14,15)

2-methyl-2-(phenylmethoxycarbonylamino)propanoic acid

Z-Aib-OH; 15030-72-5; N-Cbz-2-methylalanine; 2-(((Benzyloxy)carbonyl)amino)-2-methylpropanoic acid; 2-methyl-2-(phenylmethoxycarbonylamino)propanoic acid; Alanine, 2-methyl-N-[(phenylmethoxy)carbonyl]-; N-Carbobenzyloxy-2-methylalanine; MFCD00004190;

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

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

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.

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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 : PEG300 ：Tween 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 : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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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

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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.

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 (Please use freshly prepared in vivo formulations for optimal results.)