2-Amino-3-methylhexanoic acid: Properties, Handling & Lab Use
2-Amino-3-methylhexanoic acid: Properties, Handling & Lab Use
2-Amino-3-methylhexanoic acid is a non-proteinogenic, beta-methyl-branched aliphatic amino acid valued as a versatile building block in peptide synthesis, medicinal chemistry, and metabolic studies.
- CAS Number
- Not confirmed in source material — see review flag
- Molecular Formula
- C7H15NO2
- Molecular Weight
- 145.20 g/mol
- Compound Class
- Non-proteinogenic alpha-amino acid with beta-methyl branching
- Stereocenters
- Two stereocenters at C-2 and C-3; multiple diastereomers possible
- SKU
- A1051907
Chemical Identity and Physical Properties
2-Amino-3-methylhexanoic acid is an aliphatic, non-proteinogenic alpha-amino acid with the molecular formula C7H15NO2 and a molecular weight of approximately 145.20 g/mol. Its structure features an amino group at the alpha-carbon (C-2) and a methyl substituent at the beta-carbon (C-3), yielding a branched six-carbon backbone. The presence of two adjacent stereocenters at C-2 and C-3 gives rise to up to four possible stereoisomers (two pairs of enantiomers). Researchers should confirm the specific stereochemical configuration of the lot they are working with, as biological activity and conformational effects in peptides can differ substantially between diastereomers.
In its pure form the compound is expected to be a white to off-white crystalline solid, freely soluble in water and dilute aqueous acid or base, and sparingly soluble in most non-polar organic solvents — a solubility profile typical of alpha-amino acids. Exact melting point, optical rotation, and specific pKa values are not confirmed in the available source material and should be obtained from the certificate of analysis (CoA) supplied with SKU A1051907.
Storage and Handling Guidelines
Storage: Store 2-Amino-3-methylhexanoic acid (SKU A1051907) in a tightly sealed container under cool, dry conditions, away from light, moisture, and incompatible materials such as strong oxidising agents and strong acids or bases. A storage temperature of 2–8 °C or room temperature (15–25 °C) is typical for solid amino acid reagents; consult the product label and CoA for the lot-specific recommendation.
Handling precautions: Although alpha-amino acids are generally of low acute toxicity, standard laboratory good-practice precautions should be observed. Wear appropriate personal protective equipment (PPE) including nitrile gloves, safety glasses, and a laboratory coat. Avoid generating and inhaling fine dust. Work in a well-ventilated area or fume hood when weighing large quantities. No specific hazard classification for this compound is confirmed in the available source material; consult the Safety Data Sheet (SDS) prior to use.
Reconstitution: For aqueous solutions, dissolve the compound in ultrapure water or dilute buffer adjusted to the desired pH. If solubility is limited at neutral pH, brief adjustment to mildly acidic conditions (e.g., addition of a small volume of 0.1 M HCl) typically improves dissolution. Prepare fresh solutions or aliquot and store frozen to prevent degradation.
Research Applications
Peptide synthesis: Beta-methyl amino acids such as 2-Amino-3-methylhexanoic acid are well-established tools in peptide chemistry. The beta-methyl group restricts the phi/psi dihedral angles of the backbone, enabling researchers to introduce conformational constraints into peptide sequences, promote helical or turn structures, and improve metabolic stability relative to the corresponding unmethylated parent residue. Such modifications are widely explored in the design of bioactive peptides, peptidomimetics, and cyclic peptides.
Medicinal chemistry: Non-proteinogenic amino acids with hydrophobic side chains are used as scaffold components in drug-discovery programmes targeting proteases, transporters, and receptor-binding sites. The extended, branched aliphatic side chain of 2-Amino-3-methylhexanoic acid may mimic or replace leucine, isoleucine, or norleucine residues while providing additional steric bulk and metabolic resistance.
Biosynthetic and metabolic studies: Structurally unusual amino acids are employed as isotopic or chemical probes to investigate amino acid metabolism, aminoacyl-tRNA synthetase specificity, and nonribosomal peptide synthetase (NRPS) substrate scope. 2-Amino-3-methylhexanoic acid may serve as a substrate or inhibitor in enzymatic assays focused on branched-chain amino acid pathways.
Note: Specific published experimental protocols referencing this exact compound were not identified in the available source material. Researchers are encouraged to consult the primary literature and perform feasibility studies under their own experimental conditions.
Quality, Purity and Analytical Characterisation
When using 2-Amino-3-methylhexanoic acid (SKU A1051907) in sensitive applications such as peptide coupling or enzyme assays, it is important to verify the purity and stereochemical integrity of the reagent. Recommended analytical approaches include:
- HPLC or UHPLC: Reversed-phase or chiral-phase HPLC provides quantitative purity assessment and can resolve diastereomers. The CoA for each lot from Aladdin Scientific should specify the reported purity value.
- NMR spectroscopy: 1H and 13C NMR confirm structural identity; NOESY or coupling-constant analysis can assist in relative stereochemical assignment at C-2/C-3.
- Optical rotation or chiral HPLC: Used to confirm the enantiomeric excess (ee) of a given lot when enantiopure material is required.
- Mass spectrometry: ESI-MS or HRMS confirms the molecular ion consistent with C7H15NO2 (MW 145.20).
Always request and review the Certificate of Analysis before use. Contact Aladdin Scientific technical support if additional analytical data are required for your application.
Ordering Information and Technical Support
2-Amino-3-methylhexanoic acid is available from Aladdin Scientific under SKU A1051907. To place an order, request a quotation, or obtain a Safety Data Sheet (SDS) or Certificate of Analysis (CoA), please visit the Aladdin Scientific website or contact your regional sales representative.
For technical enquiries regarding application suitability, custom pack sizes, or bulk quantities, the Aladdin Scientific technical support team can be reached through the contact channels listed on the product page. When contacting support, please quote the SKU number A1051907 and provide details of your intended application to enable the most accurate guidance.
Frequently asked questions
What is 2-Amino-3-methylhexanoic acid used for in research?
2-Amino-3-methylhexanoic acid is primarily used as a building block in peptide synthesis, where the beta-methyl group introduces conformational constraints that can stabilise secondary structures and enhance metabolic stability. It is also explored in medicinal chemistry as a non-proteinogenic residue to modulate the pharmacological properties of peptide-based drug candidates, and in biochemical studies of branched-chain amino acid metabolism.
How many stereocenters does 2-Amino-3-methylhexanoic acid have, and does stereochemistry matter?
The compound contains two stereocenters at C-2 (alpha-carbon) and C-3 (beta-carbon), giving rise to up to four stereoisomers. Stereochemistry is critically important: different diastereomers and enantiomers can display substantially different conformational preferences when incorporated into peptides and may exhibit different levels of biological activity. Researchers should confirm the specific stereochemical configuration from the Certificate of Analysis for SKU A1051907 before use.
What solvents are recommended for dissolving 2-Amino-3-methylhexanoic acid?
As a zwitterionic alpha-amino acid, 2-Amino-3-methylhexanoic acid is expected to dissolve best in water or aqueous buffers. Solubility can be improved by adjusting the pH to mildly acidic or basic conditions. Dimethyl sulfoxide (DMSO) may be used as a co-solvent for applications requiring organic solvent compatibility, though the specific solubility profile should be verified experimentally for the intended application.
How should I store 2-Amino-3-methylhexanoic acid (SKU A1051907) to maintain stability?
Store the compound in a tightly sealed container in a cool, dry, and dark environment, protected from moisture and incompatible materials. Typical storage conditions for solid amino acid reagents are 2–8 °C or room temperature; always verify the specific recommendation on the product label and CoA. Aqueous solutions should be freshly prepared or stored frozen in aliquots.
References
- Balaram, P. Non-standard amino acids in peptide design and protein engineering. Current Opinion in Structural Biology, 1992. General reference for beta-methyl amino acids in peptide chemistry.
- Karle, I. L.; Balaram, P. Structural characteristics of alpha-helical peptide molecules containing Aib residues. Biochemistry, 1990. Background on conformationally constrained amino acids in helix stabilisation.
- Aladdin Scientific. Product page for 2-Amino-3-methylhexanoic acid, SKU A1051907. Aladdin Scientific internal product data.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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