(2S,3R)-2-amino-3-hydroxy-4-methyl-valeric Acid is a stereodefined amino acid derivative featuring a β-hydroxy side chain and a branched, methyl-substituted valeryl skeleton, with the (2S,3R) configuration specified at the α-amino-bearing carbon and the hydroxyl-bearing carbon. The molecule contains both an amino group and a carboxyl group, and the side-chain hydroxyl provides hydrogen-bonding and polarity that can influence conformational preferences and chemical derivatization during peptide or scaffold synthesis. It is used as a building block for preparing modified peptides and amino acid analogues in structure-activity studies, and its functionalized side chain supports incorporation into larger synthetic sequences where controlled stereochemistry and hydroxyl functionality are required.
CAT No: CP07003
(2S,3R)-2-amino-3-hydroxy-4-methyl-valeric Acid is a stereodefined, non-proteinogenic amino acid featuring a secondary amino group and a side-chain hydroxyl, providing both hydrogen-bonding capability and a handle for further functional derivatization. Its specific (2S,3R) configuration makes it useful when stereochemical fidelity matters in downstream synthesis, such as in building chiral fragments for peptide-like scaffolds or medicinal chemistry intermediates. The free amino acid form is commonly selected when direct incorporation into coupling workflows or conversion into protected/activated derivatives is required for structure-activity or stereochemical studies.
1. Chiral Building Block Synthesis
(2S,3R)-2-amino-3-hydroxy-4-methyl-valeric Acid is used as a stereochemically defined chiral building block for the preparation of amino acid-derived intermediates in medicinal chemistry and peptidomimetic development. Synthetic teams rely on the hydroxyl-bearing side chain to introduce controlled polarity and hydrogen-bonding interactions into larger frameworks, while the fixed (2S,3R) stereochemistry supports consistent structure generation for SAR (structure-activity relationship) campaigns. In practice, researchers often convert this amino acid into activated derivatives or protected forms to enable coupling into larger fragments, including constrained or hydroxyl-functional analogs where stereochemical outcomes are critical.
2. Peptidomimetic And Analog Assembly
(2S,3R)-2-amino-3-hydroxy-4-methyl-valeric Acid serves as a practical precursor for assembling peptide-like structures and non-natural analogs where an amino acid motif with a hydroxyl side chain is required. Chemical biology and medicinal chemistry groups frequently incorporate such stereodefined fragments to probe how side-chain hydroxyl positioning and chirality influence conformation, recognition, and overall scaffold properties in peptide-mimetic series. The amino and hydroxyl functionalities support downstream derivatization strategies used to create analog libraries, including routes that generate coupling-ready intermediates for segment condensation or sequential fragment assembly.
3. Stereochemical Reference And Derivatization
(2S,3R)-2-amino-3-hydroxy-4-methyl-valeric Acid is also used as a stereochemical reference material and derivatization starting point in analytical method development and chiral characterization workflows. Laboratories developing LC/GC methods, chiral separation conditions, or identity confirmation protocols benefit from having a defined (2S,3R) amino acid with an unprotected hydroxyl group that can be selectively derivatized to enhance detectability or chromatographic behavior. This reference utility extends to quality control of intermediate stereochemistry during pharmaceutical intermediate development, where establishing the correct stereochemical configuration of hydroxyl-containing chiral amino acid fragments is essential.
4. Pharmaceutical Intermediate Development
(2S,3R)-2-amino-3-hydroxy-4-methyl-valeric Acid is commonly positioned as a specialized pharmaceutical intermediate for manufacturing routes that require a chiral, hydroxyl-functional amino acid fragment. Process development teams use such building blocks to construct larger stereodefined intermediates that later undergo coupling, protection-group management, or functional group interconversions to reach advanced synthetic targets. The presence of both an amino group and a secondary hydroxyl supports flexible downstream transformation strategies, enabling the creation of intermediates used in the synthesis of hydroxyl-containing chiral motifs across small-molecule and peptide-inspired programs.
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