2-Amino-3-methylhexanoic acid: Properties, Uses & Lab Guide

2-Amino-3-methylhexanoic acid is a non-proteinogenic, beta-methyl-branched alpha-amino acid used as a chiral building block in peptide synthesis and medicinal chemistry research.

Chemical Name

2-Amino-3-methylhexanoic acid

Molecular Formula

C7H15NO2

Molecular Weight

145.20 g/mol

Compound Class

Non-proteinogenic alpha-amino acid

Key Stereocenters

Two stereocenters at C-2 and C-3 (up to four possible stereoisomers)

Aladdin SKU

A1051907

Chemical Identity and Structure

2-Amino-3-methylhexanoic acid (molecular formula C₇H₁₅NO₂; MW 145.20 g/mol) is a branched-chain, non-proteinogenic alpha-amino acid. Its structure features an alpha-amino group (–NH₂), an alpha-carboxylic acid (–COOH), and a beta-methyl substituent on a six-carbon backbone, creating two adjacent stereocenters at C-2 and C-3. This substitution pattern gives rise to up to four possible stereoisomers (2S,3S), (2R,3R), (2S,3R), and (2R,3S), making stereochemical identity a critical specification parameter when ordering.

The compound is structurally related to isoleucine (2-amino-3-methylpentanoic acid) but carries an additional methylene unit in the alkyl side chain, conferring distinct steric and lipophilic properties compared with its proteinogenic counterpart.

Research Applications

As a beta-methyl-branched non-canonical amino acid, 2-Amino-3-methylhexanoic acid serves several roles in chemical biology and pharmaceutical research:

• Peptide and peptidomimetic synthesis: Incorporation of beta-methyl amino acids into peptide chains can restrict backbone conformational freedom, stabilise specific secondary structures (e.g., helices or beta-turns), and improve proteolytic stability—properties highly desirable in drug-candidate peptides.
• Medicinal chemistry: The compound acts as a scaffold for structure–activity relationship (SAR) studies, allowing researchers to explore how side-chain length and beta-branching affect receptor binding or enzymatic recognition.
• Natural product analogue synthesis: Several bioactive natural products and antibiotics contain analogous beta-methyl amino acid residues; this building block facilitates their total synthesis or analogue preparation.
• Stereochemistry studies: With two stereocenters, the compound provides a model system for studying asymmetric synthesis methodologies and chiral resolution techniques.

Handling, Storage, and Safety Guidelines

Follow standard laboratory good practice when working with 2-Amino-3-methylhexanoic acid:

• Personal Protective Equipment (PPE): Wear appropriate laboratory coat, chemical-resistant gloves, and safety glasses. Avoid inhalation of fine powder.
• Storage: Store in a tightly sealed container in a cool, dry, well-ventilated area away from incompatible materials. Refrigeration (2–8 °C) is recommended for long-term preservation of stereochemical integrity; confirm exact conditions on the product Certificate of Analysis (CoA).
• Hygroscopicity: As a zwitterionic amino acid solid, the compound may be moderately hygroscopic; equilibrate to room temperature before opening to minimise moisture uptake and prevent condensation on the material.
• Solubility: Alpha-amino acids of this type are typically soluble in water (especially at acidic or basic pH) and in polar protic solvents such as methanol. Solubility in non-polar organic solvents is generally low without derivatisation.
• Disposal: Dispose of waste in accordance with local institutional and governmental regulations for laboratory chemicals.

Note: Consult the product Safety Data Sheet (SDS) for full hazard classification and regulatory information. SDS is available from Aladdin Scientific upon request.

Quality, Purity, and Ordering Information

When procuring 2-Amino-3-methylhexanoic acid for research use, consider the following quality parameters:

• Purity: Confirm purity grade (typically reported by HPLC) on the Certificate of Analysis. Higher purity grades (≥98%) are recommended for quantitative biochemical assays and pharmacological studies.
• Stereoisomeric identity: Verify which stereoisomer(s) are present and the enantiomeric/diastereomeric excess (ee/de) values, as these directly impact experimental outcomes in chiral environments.
• Lot traceability: Record lot numbers for reproducibility and regulatory compliance in GMP-adjacent research.
• Aladdin SKU: A1051907 — available from Aladdin Scientific. Contact your regional Aladdin representative or visit the product page for current pricing, pack sizes, and lead times.

Frequently asked questions

What is 2-Amino-3-methylhexanoic acid used for in research?

It is primarily used as a non-proteinogenic amino acid building block in peptide and peptidomimetic synthesis, medicinal chemistry SAR studies, and natural product analogue preparation. Its beta-methyl branching confers conformational rigidity and enhanced proteolytic stability to peptide constructs.

How many stereoisomers does 2-Amino-3-methylhexanoic acid have, and why does this matter?

The compound possesses two stereocenters (C-2 and C-3), giving rise to up to four possible stereoisomers. In biological and chemical research, different stereoisomers can exhibit markedly different activities, binding affinities, and metabolic profiles, so verifying stereochemical identity before use is essential.

What are the recommended storage conditions for 2-Amino-3-methylhexanoic acid?

Store the compound in a tightly sealed container in a cool, dry, and well-ventilated area. Refrigeration at 2–8 °C is generally recommended for long-term storage to maintain stability and stereochemical integrity. Always consult the product Certificate of Analysis and Safety Data Sheet for lot-specific guidance.

Is 2-Amino-3-methylhexanoic acid soluble in water?

Like most alpha-amino acids, it is expected to show solubility in water, particularly at acidic or basic pH where the zwitterionic equilibrium is shifted. Solubility in polar protic solvents such as methanol is also anticipated. Researchers should perform solubility testing under their specific experimental conditions and consult the CoA for confirmed data.

References

1. Barrett, G. C. & Elmore, D. T. Amino Acids and Peptides. Cambridge University Press, 1998. (General reference on amino acid chemistry and properties.)
2. Cativiela, C. & Diaz-de-Villegas, M. D. Stereoselective synthesis of quaternary alpha-amino acids. Tetrahedron: Asymmetry, 1998–2007 series. (Background on beta-methyl amino acid synthesis strategies.)
3. Aladdin Scientific product page: 2-Amino-3-methylhexanoic acid, SKU A1051907. (Product specifications and Certificate of Analysis.)

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.