(2R,3S)-2-amino-3-hydroxy-4-methyl-valeric acid is a stereodefined, nonstandard amino acid featuring an amino group and a carboxyl group alongside a secondary hydroxyl substituent and a branched 4-methyl side chain derived from a hydroxy-methyl-valeric acid framework. The (2R,3S) configuration specifies the relative stereochemistry at the α-carbon and the hydroxyl-bearing carbon, and the molecule contains a free alcohol that can participate in hydrogen bonding and can be chemically functionalized for downstream derivatization. In research and synthesis, it is used as a building block for preparing modified peptides and amino acid derivatives, and its hydroxyl functionality provides a handle for constructing conjugates or for generating protected or functionalized analogues used in structure-activity studies and analytical labeling workflows.
CAT No: CP07004
(2R,3S)-2-amino-3-hydroxy-4-methyl-valeric acid is a chiral amino acid building block bearing a secondary alcohol at C3 and an amino group at C2, making it useful for constructing stereodefined, oxygen-functionalized side chains in peptide and peptidomimetic frameworks. Its defined (2R,3S) configuration supports structure-controlled synthesis of constrained analogs, while the hydroxyl functionality provides a handle for further derivatization or controlled protection during downstream assembly. Researchers commonly use this type of amino acid scaffold to introduce hydroxyl-bearing motifs that are valuable for medicinal chemistry SAR studies and for generating chemically well-defined intermediates for custom peptide synthesis.
1. Peptidomimetic Building Blocks
(2R,3S)-2-amino-3-hydroxy-4-methyl-valeric acid is used as a stereodefined building block in peptidomimetic and modified peptide design, where incorporation of a hydroxyl-bearing carbon chain is required to mimic polar interactions or to tune hydrogen-bonding patterns. Medicinal chemistry groups and peptide development teams select this scaffold when they need a controlled (2R,3S) stereochemical outcome and an oxygen-functionalized side chain that can be further protected or functionalized to match the requirements of a larger synthetic sequence. The amino and hydroxyl groups enable downstream conversion into protected coupling-ready forms and allow chemists to prepare analog series for SAR workflows where small stereochemical or functional changes can be systematically evaluated.
2. Protected Derivative Intermediates
(2R,3S)-2-amino-3-hydroxy-4-methyl-valeric acid serves as a practical intermediate for preparing protected amino acid derivatives used in custom synthesis programs, including the preparation of coupling partners for complex fragment assembly. Because the molecule contains both an amino functionality and a secondary alcohol, it is frequently routed through protection strategies that allow selective reactivity control during multi-step intermediate manufacturing. Pharmaceutical intermediate development teams use this type of chiral amino alcohol-containing amino acid to generate well-defined intermediates for downstream coupling chemistry, enabling consistent handling in parallel synthesis and scale-up-oriented workflows where stereochemical integrity and functional group compatibility are critical.
3. Chiral Synthesis For SAR
(2R,3S)-2-amino-3-hydroxy-4-methyl-valeric acid is applied in chiral synthesis campaigns aimed at producing stereochemically consistent analogs for structure-activity relationship studies. Organic and medicinal chemists rely on such defined stereocenters to limit conformational and stereochemical variability across an analog set, particularly when the hydroxyl-bearing side chain is intended to influence binding-site complementarity or physicochemical properties. The presence of a hydroxyl group also supports targeted derivatization (for example, conversion to protected forms or functionalized alcohol derivatives) so that analogs can be diversified while maintaining the same stereochemical core, which is valuable for systematic SAR generation and for preparing defined reference materials used during lead optimization.
4. Analytical Reference And Method Development
(2R,3S)-2-amino-3-hydroxy-4-methyl-valeric acid is used as a defined chiral reference material in analytical method development and characterization workflows for amino acid derivatives and related intermediates. Laboratories developing LC-based separations, chiral analysis, or characterization panels for oxygen-functionalized amino acid derivatives may include this scaffold to verify retention behavior, stereochemical integrity, and derivatization outcomes. Its well-defined stereochemistry and functional group pattern make it a useful benchmark compound when validating analytical procedures that must distinguish closely related amino acid building blocks or confirm the identity of hydroxyl-containing intermediates generated during synthesis.
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