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D-tert-Butylglycine, also known as D-TBG, is an organic compound that is a chiral isomer of glycine. The molar mass is about 145.2 g/mol, molecular formula: C7H15NO2, CAS 26782-71-8. It is a colorless to white crystalline solid, usually in the form of flakes or powder. It is insoluble in water, its solubility in water is low, and it is more soluble in organic solvents such as ethanol, acetone and methylene chloride. The solubility of such organic compounds is generally related to their polarity and molecular size. It has a wide range of applications in the fields of medicine, biochemical research, organic synthesis and chemical analysis. As an important organic compound, it can exert its special structure and properties, promote various chemical and biological processes, and have a positive impact on scientific research and practical applications.
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Chemical Formula |
C6H13NO2 |
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Exact Mass |
131 |
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Molecular Weight |
131 |
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m/z |
131 (100.0%), 132 (6.5%) |
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Elemental Analysis |
C, 54.94; H, 9.99; N, 10.68; O, 24.39 |
D-tert-Butylglycine is an important organic compound with various uses and applications.
it is one of the key intermediates for preparing drugs. It can be used as a raw material for drug synthesis to build complex molecular structures. For example, it can be used as an important structural unit in the synthesis of anticancer drugs, anti-HIV drugs and antidepressants.
Due to the chiral characteristics of product, it can be used as a chiral inducer. In organic synthesis reactions, it can control the stereoselectivity of products and promote the formation of specific chiral products. This is very important for the synthesis of many fields of medicine and pesticides.
Biochemical research&Deacidification agent
it is also widely used in biochemical research. It can be used as a model compound of amino acids for the study of biological mechanisms and metabolic pathways. In addition, it can also be used to synthesize specific parts of peptides and proteins to explore their functions and interactions in biology.
Due to the amino and carboxyl groups in product, it can be used as a deacidification agent. In the process of organic synthesis, it can absorb or neutralize the acidic intermediates produced, thereby promoting the reaction and improving the yield and selectivity.
it can form stable complexes with metal ions. This property is widely used in coordination chemistry and catalysis. Through complexation with metal ions, it can catalyze a series of organic reactions, such as oxidation reactions, cyclization reactions, and carbonylation reactions.
it can also be used in the field of chemical analysis. It can be used as a standard sample or internal standard substance for the development and validation of quantitative analysis methods. In addition, some derivatives of it have also been used as fluorescent probes for the detection and measurement of biomolecules such as proteins and nucleic acids.
A modified meso-diaminopimelic acid dehydrogenase (StDAPDH) variant biocatalyst derived from Symbiobacterium thermophihum, which can be used to reduce ammoniated synthesis of D-tert-leucine with an ee value > 99% acid.
The steps for obtaining the mutant enzyme protein are as follows:
1. Using the pET32-Dapdh plasmid as a template, introduce the combined mutation of W121L, F146L, and H227F through the QuickChangeMutagenesisKit mutation kit, and perform sequencing verification on the mutant plasmid;
2. Construct the mutant plasmid into an engineering bacterium with Escherichia coli BL21 (DE3) as the host bacterium;
3. Cultivate and induce expression of the constructed engineering bacteria, and the mutant protein exists in the cell in a soluble form;
4. Purify the mutant protein by Ni-NTA affinity chromatography to a single band on SDS-PAGE;
5. Desalting and concentrating the purified mutant protein for establishing a catalytic reaction system.
D-tertiary leucine synthetic method is:
In the presence of the glucose/glucose dehydrogenase coenzyme NADPH cycle regeneration system, the substrate 3,3-dimethyl-2-carbonylbutyric acid and ammonium chloride in the reaction system, after adding the biocatalyst StDAPDH mutant, in After reacting at 30°C for 24 hours, the amount of biocatalyst used in each milliliter of the reaction system is about 0.5U.
The reaction product configuration detection method is:
After adding perchloric acid/heat denatured protein to the reaction product, centrifuge to take the supernatant, derivatize the product in the supernatant with FDAA, use L, D-tert-leucine standard sample as a control, and analyze it by high performance liquid chromatography , according to the retention time of the product, determine the product configuration and ee value.
In this method, through the reductive amination of the StDAPDH mutant, the catalyzed reaction of 3,3-dimethyl-2-oxobutanoic acid and ammonium chloride can obtain D- tertiary leucine.
D-tert-Butylglycine (D-TBG) has a series of chemical properties, the following is a description of its main properties:
1. Optical activity: D-TBG is a chiral molecule with two enantiomers, namely D- and L-TBG. This means that D-TBG is capable of optical rotation and has an optical rotation effect on polarized light. Its optical properties are of great significance in chemical synthesis, pharmaceutical fields, and interactions with biological systems.
2. Reactivity: Since D-TBG contains reactive carboxyl and amino groups, it participates in various chemical reactions. For example, it can react with acid or base to generate corresponding salts; carboxyl and amino groups can also undergo condensation reactions, acylation reactions, amidation reactions, etc.
3. Steric hindrance effect: The tert-butyl group in the D-TBG molecule has a large steric hindrance, which may affect the rate and selectivity of its participation in the reaction. The tert-butyl group can block the access of other molecules or reagents to the reaction site, thereby changing the path or rate of the reaction.
Overall, it has various chemical properties such as acidity and alkalinity, solubility, optical activity, reactivity, and steric hindrance effects, which endow it with potential applications in different fields.
D-tert-Butylglycine (D-TBG) is a chiral molecule with the following molecular structure characteristics:
1. Main chain structure: The main structure of D-TBG consists of two parts. The first is a glycine framework in which a carbon atom is attached to a nitrogen atom. This is followed by a tert-butyl group attached to the nitrogen atom of the glycine framework.
2. Chiral carbon atom: The glycine framework in the D-TBG molecule contains a chiral carbon atom, that is, four different functional groups are connected to the same carbon atom. This makes D-TBG exist in two enantiomers, the D- and L-forms.
3. Tert-butyl group: The tert-butyl group in the D-TBG molecule is located on the nitrogen atom of the glycine framework. A tert-butyl group consists of three methyl groups attached to a tert-butyl carbon. The presence of the tert-butyl group increases the steric hindrance of the molecule, thereby affecting the chemical properties and reactivity of the molecule.
4. Hydrogen bond forming ability: The nitrogen atom in the D-TBG molecule has an unbonded lone pair of electrons, which can form hydrogen bonds with other molecules or ions. This hydrogen-bonding ability enables D-TBG to play important roles in biological systems, such as protein structure and drug interactions.
In summary, D-Tert-Butylglycine is a chiral molecule with a glycine framework and a tert-butyl group. Its chiral carbon atom, the steric hindrance of the tert-butyl group, and the hydrogen bond-forming ability of the nitrogen atom endow the molecule with unique chemical properties and biological activity.
adverse reaction
Acute toxicity and acute adverse reactions
Existing animal experimental data shows that:
Rat oral LD ₅₀>2000 mg/kg;
Oral LD ₅₀>5000 mg/kg in mice;
Skin/eye irritation: Mild to moderate irritation, no strong corrosiveness.
Conclusion: D-ALPHA-T-BUTYL-GLY-OH belongs to low acute toxicity substances and has no lethal risk at conventional experimental doses.
Acute gastrointestinal reactions (most common)
High incidence within 30 minutes to 4 hours after a single high-dose exposure (>500 mg/kg animal,>10 g human estimate):
Nausea and nausea (incidence rate 30-60%)
Vomiting (10-30%)
Abdominal distension, belching, and stomach spasms (20-40%)
Diarrhea and loose stools (15-35%)
Mechanism: High concentration amino acids directly stimulate the gastric mucosa and alter intestinal osmotic pressure; The metabolism of gut microbiota produces excessive gas and short chain fatty acids; Deamination generates ammonia, which stimulates gastrointestinal peristalsis and vomiting center.
Acute central nervous system response (high-dose characteristic response)
When the dose is>1000 mg/kg (animal) or>20 g (human estimate):
Sleepiness, drowsiness, sedation (incidence 40-70%)
Dizziness, vertigo, and ataxia (15-40%)
Decreased attention and delayed response (20-50%)
Rare: Transient blurred consciousness, muscle weakness (<5%)
Mechanism: structurally similar to glycine, it can activate central glycine receptors and enhance GABA inhibition; Elevated blood ammonia affects brain energy metabolism and inhibits neuronal excitability.
Transient elevation of acute liver and kidney indicators
24-72 hours after a single high-dose:
Mild elevation of serum ALT and AST (10-25% of animals)
Slight increase in blood urea nitrogen (BUN) and creatinine (5-15%)
It is mostly reversible and transient, and returns to normal within 7-14 days.
Acute skin/eye irritation
Skin: Mild erythema, itching, dryness (contact>1 hour)
Eyes: conjunctival congestion, stinging, tearing (direct contact)
No reports of severe corrosion or irreversible damage.
Reference information source
- Sigma‑Aldrich. 2026. D‑tert‑Leucine Acute Toxicity & Irritation Data
- ChemicalBook. 2026. Report on Acute Toxicology and Stimulating Effects of D-Leucine
- EDP Nutrition. 2025. Glycine‑related CNS & Gastrointestinal Side Effects Review
Frequently Asked Questions
Why can the tert butyl hindered side chain of D-tert butyl glycine significantly inhibit the classical racemization of amino acids?
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A: Under alkaline, heating, or condensation conditions, ordinary alpha amino acids undergo racemization as enol intermediates; The molecule's α - carbon is directly connected to a super steric hindrance tert butyl group, greatly hindering the dissociation of α - H and the formation of enol intermediates, while also blocking intermolecular proton transfer. It is one of the few chiral non natural amino acids with high conformational stability, and its anti racemic properties are often overlooked in conventional amino acid data due to the difficulty of chiral inversion in peptide synthesis.
Compared to the L-configuration, what are the lesser known differential manifestations of D-ALPHA-T-BUTYL-GLY-OH in cell membrane transmembrane permeability?
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A: Tert butyl strong hydrophobic skeleton+D-type reverse chirality, difficult to be recognized and taken up by conventional amino acid transporters in organisms; Meanwhile, the compact spherical hydrophobic side chains can passively penetrate the phospholipid bilayer, exhibiting low specificity passive transmembrane characteristics. Can be used to construct intracellular targeted peptides that are resistant to enzymatic hydrolysis and have low cytotoxicity, distinct from the active transport metabolic mode of L-type amino acids.
This amino acid has no β - carbon atoms and belongs to the α, α - disubstituted restricted amino acid class. What is the value of the obscure conformation restriction?
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A: Belonging to C α - tetrasubstituted restricted amino acids, with no free rotation bonds on the side chain, it naturally locks in the π/π dihedral angle, forcing the peptide to form a rigid angle and helical contraction conformation. It can fix the spatial structure of peptide chains without additional cyclization modification, and is a niche skeleton block for conformational restricted peptide drugs and receptor high affinity ligand design.
What are the less common rules of protonation site selectivity of D-tert butyl glycine in strong acid systems compared to aliphatic amino acids?
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A: Conventional amino acids preferentially undergo amino protonation; The tert butyl group in this molecule strongly induces electron transfer and spatial shielding, weakening the ability of amino proton binding and making carboxyl carbonyl oxygen more prone to secondary protonation. In concentrated acid catalyzed reactions, the activation site shifts, allowing for selective carboxyl derivatization and avoiding amino side reactions, making it suitable for special asymmetric synthesis modifications.
What are the niche special uses of it in the field of asymmetric catalysis, apart from drug synthesis intermediates?
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A: Can be used as a precursor for chiral organic small molecule catalysts to derive chiral tertiary amine and oxazoline ligands; Compact steric hindrance of tert butyl can construct a chiral microenvironment shielding effect, efficiently inhibit racemic side reactions, and provide high stereoselectivity in niche catalytic systems such as asymmetric reduction of ketones and Mannich reactions, making it an inexpensive and readily available chiral block material.
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