(2S,3S)-2-amino-3-hydroxy-4-methyl-valeric acid is a stereochemically defined amino acid derivative featuring an amino group and a carboxyl group on a branched aliphatic backbone, with a secondary alcohol substituent at C-3 and a methyl substituent at C-4. The (2S,3S) configuration specifies the relative stereochemistry around the amino-bearing and hydroxy-bearing centers, and the side-chain hydroxyl functionality provides hydrogen-bonding and polarity that can influence peptide coupling and downstream derivatization. This compound is used as a building block for preparing modified peptides and amino acid analogues in structure-activity and chemical biology studies, as well as for analytical method development where defined stereochemical and functional-group features are required.
CAT No: CP07002
(2S,3S)-2-amino-3-hydroxy-4-methyl-valeric acid is a stereochemically defined, non-proteinogenic amino acid characterized by an amino group and a side-chain secondary alcohol, along with a branched alkyl substituent that increases hydrophobic character. Its defined (2S,3S) configuration makes it a useful chiral building block for constructing stereochemically rich intermediates in peptide and small-molecule synthesis, where the hydroxyl functionality can be used for downstream derivatization or protection strategies.
1. Stereoselective Building Block Synthesis
(2S,3S)-2-amino-3-hydroxy-4-methyl-valeric acid is used as a chiral amino acid building block in the preparation of stereodefined intermediates for medicinal chemistry and peptidomimetic development. Researchers and process chemists value the combination of an amino functionality with a secondary alcohol, since it supports orthogonal functionalization workflows that lead to alcohol-modified side chains, constrained fragments, and analogs that require strict stereochemical control. This compound is especially relevant when a branched alkyl motif and a hydroxyl-bearing stereocenter must be carried through to later stages of synthesis without losing stereochemical integrity.
2. Peptide Analog And Fragment Coupling
(2S,3S)-2-amino-3-hydroxy-4-methyl-valeric acid serves as an amino acid fragment for assembling peptide analogs and constrained residues in custom peptide synthesis and structure-activity relationship (SAR) studies. The presence of the amino group enables incorporation into amide-forming coupling strategies, while the side-chain hydroxyl provides a handle for generating hydroxy-containing analogs that can be used to probe structure-property relationships, such as changes in hydrogen-bonding patterns and local polarity. Common downstream workflows include conversion into activated coupling forms and subsequent incorporation into short peptide sequences or peptidomimetic scaffolds used in chemical biology and drug discovery research.
3. Alcohol-Derived Functionalization Intermediates
(2S,3S)-2-amino-3-hydroxy-4-methyl-valeric acid is frequently selected as a precursor for alcohol-derived derivatives, where the secondary hydroxyl is the key functional element for further derivatization. Synthetic teams use this amino acid to access protected alcohol intermediates, ester or ether variants, and other hydroxyl-functionalized fragments that are carried into larger synthetic sequences. In practical development settings, the defined stereochemistry helps ensure that downstream transformations occur on a well-defined chiral center, which is important for maintaining the stereochemical fidelity of side-chain motifs in complex molecule synthesis.
4. Analytical Reference For Chiral Methods
(2S,3S)-2-amino-3-hydroxy-4-methyl-valeric acid is also used as a defined stereochemical reference material in analytical method development and chiral characterization workflows. Laboratories developing LC methods, chiral separations, or derivatization-based assays rely on stereochemically specified amino acid standards to evaluate retention behavior, derivatization consistency, and identity confirmation for related intermediates and analogs. The combination of amino and hydroxyl functionalities makes it a practical reference for validating analytical procedures that target both amine-containing and oxygenated stereocenters within synthetic mixtures.
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