3-Methyl-2-Ureido-Butyric Acid: Properties & Research Uses
3-Methyl-2-Ureido-Butyric Acid: Properties & Research Uses
3-Methyl-2-Ureido-Butyric Acid is a specialty ureido-functionalized amino acid derivative of interest in biochemical research, serving as a structurally defined building block for mechanistic studies involving urea-bearing metabolites and related synthetic pathways.
- Product Name
- 3-Methyl-2-Ureido-Butyric Acid
- SKU
- C1058534
- Compound Class
- Ureido amino acid derivative
- Core Functional Groups
- Ureido group (–NH–CO–NH₂), carboxylic acid, branched alkyl chain
- Supplier
- Aladdin Scientific
- Primary Research Application
- Biochemical mechanistic studies, metabolite analogue research, organic synthesis
Chemical Identity and Structure
3-Methyl-2-Ureido-Butyric Acid is an organic compound belonging to the class of ureido amino acid derivatives. Its structure combines a central alpha-carbon bearing a ureido substituent (–NH–CO–NH₂) with a branched 3-methylbutyl backbone and a terminal carboxylic acid group. This combination of functional groups places the molecule at the intersection of amino acid chemistry and urea-derivative chemistry, making it structurally analogous to naturally occurring ureido metabolites found in nitrogen metabolism pathways.
The ureido moiety is chemically significant because it mimics the guanidinium and urea functional groups present in biologically active molecules such as citrulline, an intermediate in the urea cycle. The branched methyl substituent at the 3-position introduces steric complexity that influences both the conformational behavior of the molecule and its interactions with biological targets or synthetic coupling partners.
Researchers and procurement teams should note that the compound is identified under SKU C1058534 at Aladdin Scientific and is offered as a research-grade reagent. Precise physicochemical data such as exact molecular weight, melting point, and spectroscopic profiles should be confirmed from the current Certificate of Analysis (CoA) at time of purchase.
Biological and Biochemical Relevance
Ureido-substituted amino acid derivatives occupy an important niche in biochemistry due to their structural resemblance to metabolic intermediates. The ureido functional group (–NH–CO–NH₂) is a key structural motif in several biologically occurring molecules. For instance, citrulline, a non-proteinogenic amino acid featuring a ureido side chain, plays a central role in the urea cycle and in arginine biosynthesis. Compounds structurally related to such metabolites are therefore useful as biochemical probes, enzyme substrate analogues, or reference standards in metabolomics studies.
3-Methyl-2-Ureido-Butyric Acid, with its branched alkyl chain and ureido group at the alpha position, may be of interest to researchers studying nitrogen metabolism, enzyme specificity, or the pharmacology of ureido-containing natural products. It can serve as a synthetic intermediate in the preparation of more complex ureido peptides or heterocyclic compounds derived from cyclization of the ureido and carboxylic acid moieties.
As with all research reagents, the specific biological activity and metabolic fate of this compound in cellular or in vivo systems should be experimentally validated. No confirmed bioactivity data were available in the source material; researchers are encouraged to consult primary literature for related structural analogues.
Handling, Storage, and Laboratory Safety
When working with 3-Methyl-2-Ureido-Butyric Acid, researchers should follow standard laboratory safety practices applicable to organic carboxylic acid derivatives. This includes wearing appropriate personal protective equipment (PPE) such as nitrile gloves, safety glasses, and a lab coat. Work in a well-ventilated area or fume hood when handling powders to minimize inhalation exposure.
For storage, ureido-amino acid derivatives are generally best maintained as dry solids at controlled temperatures. The specific recommended storage conditions (temperature, humidity, light sensitivity) for SKU C1058534 should be confirmed from the product label and the current CoA provided by Aladdin Scientific at the time of shipment. Avoid prolonged exposure to moisture, which can promote hydrolysis of the ureido group under acidic or basic conditions.
Stock solutions prepared in appropriate solvents (such as DMSO, water at adjusted pH, or dilute aqueous base depending on solubility) should be aliquoted and stored according to validated stability data. Researchers are advised to consult the Safety Data Sheet (SDS) for C1058534 prior to use for comprehensive hazard, first-aid, and disposal information specific to this compound.
Applications in Organic Synthesis
3-Methyl-2-Ureido-Butyric Acid is of interest to synthetic chemists as a bifunctional building block. The simultaneous presence of a free carboxylic acid, a secondary amine within the ureido group, and a branched alkyl scaffold offers multiple handles for chemical elaboration. The carboxylic acid can be activated for amide bond formation, esterification, or coupling with other nucleophiles under standard peptide coupling or carbodiimide-mediated conditions.
The ureido group itself can participate in cyclization reactions to form hydantoin or related five-membered ring heterocycles under appropriate thermal or acid/base-mediated conditions. Such cyclization chemistry is well established for ureido amino acids in the synthesis of pharmacologically relevant heterocyclic scaffolds. Researchers targeting the preparation of constrained peptidomimetics or nitrogen-rich heterocycles may find this compound a useful precursor.
Additionally, the branched 3-methyl substitution introduces a chiral center or stereochemical complexity that may be leveraged in asymmetric synthesis workflows. Confirmation of stereochemical configuration (R/S assignment) of the commercial material should be sought from the CoA or product specification sheet for C1058534.
Frequently asked questions
What is 3-Methyl-2-Ureido-Butyric Acid used for in research?
It is used as a specialty research reagent and synthetic building block. Researchers may employ it as a structural analogue of ureido metabolites, as a substrate probe in enzyme studies related to nitrogen metabolism, or as a synthetic precursor for ureido peptides and heterocyclic compounds such as hydantoins.
How should I store 3-Methyl-2-Ureido-Butyric Acid (C1058534)?
As a ureido amino acid derivative, it should generally be stored as a dry solid at controlled temperature, away from moisture and light. Specific storage conditions must be confirmed from the current Certificate of Analysis (CoA) and product label provided by Aladdin Scientific, as these are compound-specific and lot-dependent.
Is 3-Methyl-2-Ureido-Butyric Acid soluble in water?
Ureido amino acid derivatives typically show limited to moderate aqueous solubility, which can be enhanced at adjusted pH due to ionization of the carboxylic acid group. However, precise solubility data for C1058534 should be verified from the product CoA or empirically determined under your specific experimental conditions. DMSO is often used as an alternative solvent for preparing stock solutions of such compounds.
Where can I purchase 3-Methyl-2-Ureido-Butyric Acid?
3-Methyl-2-Ureido-Butyric Acid is available from Aladdin Scientific under SKU C1058534. Contact Aladdin Scientific directly or visit the product page on the Aladdin website to obtain current pricing, available quantities, purity specifications, and lead times.
Does 3-Methyl-2-Ureido-Butyric Acid have a chiral center?
The structure of 3-Methyl-2-Ureido-Butyric Acid includes an alpha-carbon bearing distinct substituents (ureido group, carboxylic acid, hydrogen, and a branched alkyl chain), which constitutes a potential chiral center. The stereochemical configuration (R or S) of the commercial material offered under C1058534 should be confirmed from the product specification sheet or CoA at the time of purchase.
References
- Lehninger, A.L., Nelson, D.L., Cox, M.M. Lehninger Principles of Biochemistry. W.H. Freeman. (General reference for urea cycle and ureido metabolite biochemistry.)
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. (General reference for ureido compound reactivity and heterocycle synthesis.)
- Aladdin Scientific. Product page for 3-Methyl-2-Ureido-Butyric Acid, SKU C1058534. Aladdin Scientific catalog.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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