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| Other Sizes |
| Targets |
As a detergent and solubilizing agent, N2-Lauroyl-L-glutamine is not designed to act on specific molecular targets but rather functions by interacting with hydrophobic protein surfaces and lipid membranes. The compound consists of a lauric acid (C12:0) fatty acyl chain attached to the alpha-amino group of L-glutamine. This amphipathic structure allows the molecule to form micelles in aqueous solution, with the hydrophobic lauroyl chain interacting with non-polar regions of proteins, thereby promoting protein solubilization and preventing aggregation. The mechanism of action in protein refolding involves the ability of the detergent to bind to exposed hydrophobic patches on denatured proteins, preventing non-specific aggregation and providing a favorable environment for the protein to refold into its native conformation. The deuterated version N2-Lauroyl-L-glutamine-d23 is not intended to have direct biological activity; it serves as an internal standard for analytical quantitation of the non-labeled compound in refolding systems.
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| ln Vitro |
Stable heavy isotopes of hydrogen, carbon, and other elements have been incorporated into drug molecules, largely as tracers for quantitation during the drug development process. Studies involving the human use of drugs labeled with deuterium suggest that these compounds may offer some advantages when compared with their nondeuterated counterparts. Deuteration has gained attention because of its potential to affect the pharmacokinetic and metabolic profiles of drugs. Deutetrabenazine is the first deuterated drug to receive Food and Drug Administration approval. This deuterated form of the drug tetrabenazine is indicated for the treatment of chorea associated with Huntington's disease as well as tardive dyskinesia. Ongoing clinical trials suggest that a number of other deuterated compounds are being evaluated for the treatment of human diseases and not merely as research tools.[1]
The primary in vitro activity of N2-Lauroyl-L-glutamine is as a protein refolding additive and solubilizing detergent in biochemistry and biotechnology applications. Studies have demonstrated that this compound can be used in a novel protein refolding system to improve the yield of correctly folded recombinant proteins from inclusion bodies. The effectiveness of N2-Lauroyl-L-glutamine as a refolding agent is attributed to its ability to interact with denatured proteins in a controlled manner, allowing the protein to slowly refold into its native three-dimensional structure while being protected from aggregation. The compound is particularly useful for refolding of membrane proteins and other difficult-to-express proteins that tend to aggregate when conventional refolding methods are used. As an acylated amino acid, N2-Lauroyl-L-glutamine exhibits surfactant properties with a critical micelle concentration (CMC) suitable for mild protein solubilization without causing denaturation. For the deuterated version, N2-Lauroyl-L-glutamine-d23 serves as a precisely matched internal standard for quantifying the non-labeled compound in protein refolding systems by LC-MS/MS. |
| ln Vivo |
Deuterated compounds may, in some cases, offer advantages over nondeuterated forms, often through alterations in clearance. Deuteration may also redirect metabolic pathways in directions that reduce toxicities. The approval of additional deuterated compounds may soon follow. Clinicians will need to be familiar with the dosing, efficacy, potential side effects, and unique metabolic profiles of these new entities.
The primary in vivo activity of N2-Lauroyl-L-glutamine has not been well characterized, as this compound is a synthetic chemical primarily used in in vitro biochemical applications such as protein refolding and solubilization. As an N-acyl amino acid containing lauric acid (dodecanoic acid, a C12:0 medium-chain saturated fatty acid) and the amino acid L-glutamine, the compound may be hydrolyzed in vivo to release lauric acid and L-glutamine. Lauric acid is a medium-chain fatty acid (MCFA) that is metabolized differently from long-chain fatty acids; it is transported directly to the liver via the portal vein, where it undergoes beta-oxidation to produce energy without requiring carnitine transport. Lauric acid has been reported to possess antimicrobial, antiviral, and anti-inflammatory activities. L-Glutamine is a conditionally essential amino acid important for intestinal health, immune function, and nitrogen transport. However, N2-Lauroyl-L-glutamine itself is not used as a therapeutic agent and is not administered in vivo. The deuterated analog is intended for in vitro analytical use only. |
| Enzyme Assay |
For the parent compound N2-Lauroyl-L-glutamine, in vitro enzyme-based assays can be performed to study its synthesis or degradation. The compound can be synthesized enzymatically using acylase I (also known as aminoacylase I, EC 3.5.1.14) from pig kidney in a glycerol-water system. A typical reaction mixture contains 50 mM phosphate buffer (pH 7.0-8.0), 20% glycerol, 50 mM L-glutamine, 50 mM lauric acid, and 0.1-1 U/mL acylase I. The reaction is incubated at 37degC for 24-72 hours with gentle shaking. Product formation is monitored by TLC or HPLC. For degradation studies, N2-Lauroyl-L-glutamine can be incubated with various esterases, lipases, or amidases to study the hydrolysis of the amide bond. The deuterated version is used as an internal standard in these studies to accurately quantify the parent compound by LC-MS/MS. The labeled internal standard can be spiked into reaction mixtures at known concentrations to correct for extraction efficiency and matrix effects during sample preparation and analysis.
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| Cell Assay |
N2-Lauroyl-L-glutamine-d23 is primarily used as an internal standard in cell-based experiments where the non-labeled parent compound is added to cells, rather than as a functional probe in cell assays. For cell viability or toxicity studies with the parent compound, suitable cell lines (e.g., HEK293, CHO, or HepG2 cells) are seeded in 96-well plates at a density of 10,000-20,000 cells per well in appropriate culture medium supplemented with 10% FBS and incubated overnight at 37degC with 5% CO2. The medium is then replaced with fresh medium containing various concentrations of N2-Lauroyl-L-glutamine (1-200 microg/mL) and incubated for 24-72 hours. Cell viability is assessed using MTT, CCK-8, or resazurin-based assays. For protein refolding experiments using cells expressing recombinant proteins, cells are lysed, and inclusion bodies are isolated by centrifugation. The isolated inclusion bodies are denatured in 6-8 M guanidine hydrochloride or urea, then diluted into refolding buffer containing N2-Lauroyl-L-glutamine as a refolding additive (0.1-1% w/v). The refolded protein is then analyzed by SDS-PAGE, Western blot, or enzymatic activity assays. The deuterated version (N2-Lauroyl-L-glutamine-d23) is used as an LC-MS/MS internal standard to quantify the concentration of the non-labeled compound in cell lysates or refolding buffers.
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| Animal Protocol |
For in vivo experiments with N2-Lauroyl-L-glutamine (unlabeled), studies are limited. If in vivo distribution or metabolism studies were to be conducted, male Sprague-Dawley rats (200-250 g) or C57BL/6 mice (20-25 g) would typically be used. The compound would be formulated in a suitable vehicle such as PBS containing up to 10% DMSO or 5% Tween 80, depending on solubility. Administration routes may include intravenous (tail vein injection), intraperitoneal, or oral gavage. Blood samples would be collected at predetermined time points (0, 15, 30, 60, 120, 240, 480, 720 minutes post-dose) and plasma separated by centrifugation. At the end of the experiment, animals would be euthanized, and tissues (liver, kidney, intestine, adipose tissue) collected, weighed, and homogenized. Tissue homogenates would be processed for analysis. The deuterated version N2-Lauroyl-L-glutamine-d23 is ideally suited for use as a tracer in such studies; it can be administered as the labeled compound, and LC-MS/MS analysis would allow precise tracking of its distribution, metabolism, and elimination. However, for typical research use, N2-Lauroyl-L-glutamine-d23 is used as an internal standard for in vitro experiments rather than being administered to animals.
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| ADME/Pharmacokinetics |
For N2-Lauroyl-L-glutamine, pharmacokinetic data are derived from the properties of its constituent parts (lauric acid and L-glutamine) rather than from direct studies on the intact compound. Lauric acid (C12:0) is a medium-chain fatty acid that is rapidly absorbed from the gastrointestinal tract and transported directly to the liver via the portal vein, bypassing the lymphatic system. Medium-chain fatty acids undergo rapid beta-oxidation in the liver to produce acetyl-CoA, which enters the TCA cycle for energy production. The elimination half-life of lauric acid is short (approximately 30-60 minutes). L-Glutamine is an amino acid with active transport systems for absorption and distribution, with a plasma half-life of approximately 1-2 hours in humans. The intact N2-Lauroyl-L-glutamine molecule, if absorbed, would likely be rapidly hydrolyzed by serum amidases or esterases to release lauric acid and L-glutamine. The deuterated compound N2-Lauroyl-L-glutamine-d23, if used as a tracer, would exhibit identical PK properties as the non-labeled compound. However, as a research reagent for in vitro applications, the compound is not typically used for PK studies in animals.
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| Toxicity/Toxicokinetics |
For N2-Lauroyl-L-glutamine, toxicity information is derived from its components lauric acid and L-glutamine, both of which are Generally Recognized as Safe (GRAS) substances. Lauric acid (dodecanoic acid) is a medium-chain saturated fatty acid naturally present in coconut oil and palm kernel oil. It is used as a food additive and dietary supplement, with a history of safe human consumption. Lauric acid has low acute toxicity; the oral LD50 in rats is >5,000 mg/kg. L-Glutamine is a naturally occurring amino acid that is safe for human consumption at doses up to 40 g/day in clinical studies. No specific toxicity data are available for the N-acylated combination N2-Lauroyl-L-glutamine itself. As a detergent and solubilizing agent, high concentrations of N2-Lauroyl-L-glutamine may cause irritation to mucous membranes and skin in laboratory handling. The deuterated analog has an identical toxicity profile. Standard laboratory safety practices should be followed when handling this compound, including the use of appropriate personal protective equipment (gloves, lab coat, safety glasses). The compound is intended for research use only and is not for human therapeutic or diagnostic applications.
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| References | |
| Additional Infomation |
N2-Lauroyl-L-glutamine is a synthetic N-acyl amino acid derivative used as a solubilizing detergent in a novel protein refolding system, as described in the scientific literature (Kudou, M. et al., Protein Expression and Purification, 2011, 75, 46; Wada, E. et al., Journal of the American Oil Chemists' Society, 2002, 79, 41). The compound can be synthesized enzymatically using acylase I from pig kidney in a glycerol-water system. N2-Lauroyl-L-glutamine-d23 is the deuterium-labeled analog of this compound, containing 23 deuterium atoms that extensively label the lauroyl (dodecanoyl) fatty acid chain. This stable isotope-labeled version serves as an internal standard for accurate LC-MS/MS quantification of the non-labeled compound in protein refolding systems, formulation studies, and biochemical assays. The extensive deuteration (23 atoms) provides a significant mass shift of +23 Da relative to the unlabeled compound, allowing unambiguous differentiation by mass spectrometry even in complex biological matrices. The compound appears as a white to off-white solid powder with purity 97% and 97% atom% D. Storage: powder at -20degC for 3 years or 4degC for 2 years; in solvent at -80degC for 6 months or -20degC for 1 month. This product is for research use only and is not for clinical or diagnostic use.
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| Molecular Formula |
C17H9D23N2O4
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|---|---|
| Molecular Weight |
351.59
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| Exact Mass |
351.38
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| CAS # |
1795786-88-7
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| PubChem CID |
71749759
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| Appearance |
Solid powder
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| LogP |
3.5
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
15
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| Heavy Atom Count |
23
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| Complexity |
359
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| Defined Atom Stereocenter Count |
1
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| SMILES |
[2H]C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C(=O)N[C@@H](CCC(=O)N)C(=O)O
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| InChi Key |
USMCNVFGYLZLGM-HZQGCWOGSA-N
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| InChi Code |
InChI=1S/C17H32N2O4/c1-2-3-4-5-6-7-8-9-10-11-16(21)19-14(17(22)23)12-13-15(18)20/h14H,2-13H2,1H3,(H2,18,20)(H,19,21)(H,22,23)/t14-/m0/s1/i1D3,2D2,3D2,4D2,5D2,6D2,7D2,8D2,9D2,10D2,11D2
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| Chemical Name |
(2S)-5-amino-5-oxo-2-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-tricosadeuteriododecanoylamino)pentanoic acid
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| HS Tariff Code |
2934.99.9001
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| 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)
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| 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
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8442 mL | 14.2211 mL | 28.4422 mL | |
| 5 mM | 0.5688 mL | 2.8442 mL | 5.6884 mL | |
| 10 mM | 0.2844 mL | 1.4221 mL | 2.8442 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.
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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