(2R,3R)-2-amino-3-hydroxy-4-methyl-valeric acid is a stereochemically defined, non-proteinogenic amino acid featuring an amino group and a carboxyl group on a branched aliphatic backbone, with a secondary hydroxyl substituent at C3 and a methyl substituent at C4. The (2R,3R) configuration specifies the relative stereochemistry around the amino-bearing carbon and the hydroxyl-bearing carbon, and the side-chain hydroxyl provides an oxygen functional group that can participate in hydrogen bonding and serve as a handle for further derivatization. As a chemically defined amino acid building block, it is used in peptide and amino acid derivative synthesis and in structure-property studies where hydroxyl-bearing, stereopure residues are required for controlled incorporation or analytical labeling.
CAT No: CP07005
(2R,3R)-2-amino-3-hydroxy-4-methyl-valeric acid is a chiral amino acid building block bearing a β-hydroxy functionality and an amino group, which makes it a useful structural motif for constructing stereodefined, oxygenated side chains in peptide and peptidomimetic frameworks. Its (2R,3R) configuration supports the preparation of constrained analogs where hydroxyl-bearing stereocenters are important for downstream structure-activity relationship studies and conformational control. As a free amino acid or amino acid intermediate form, it is commonly selected when the target scaffold requires both an amino handle for coupling and a hydroxyl group for further functionalization or for retaining polarity in the final product.
1. Peptidomimetic Building Block
(2R,3R)-2-amino-3-hydroxy-4-methyl-valeric acid is used in medicinal chemistry and chemical biology programs to assemble peptidomimetic structures that incorporate stereodefined β-hydroxy amino acid motifs. Researchers developing analog series for structure-activity relationship work frequently rely on this type of chiral, oxygenated amino acid to tune hydrogen-bonding capacity, polarity, and three-dimensional shape in non-natural peptide backbones. The presence of both an amino functionality for amide formation and a secondary alcohol for controlled derivatization enables iterative design of analogs that maintain the intended hydroxyl stereochemistry while allowing downstream modifications such as protection/deprotection strategies or conversion into alternative functional groups.
2. Stereodefined Peptide Synthesis
(2R,3R)-2-amino-3-hydroxy-4-methyl-valeric acid serves as a specialized building block for custom peptide synthesis where an oxygenated stereocenter is required in the amino acid residue. Peptide chemists use this compound to introduce a β-hydroxy-bearing side-chain element that can influence local conformation and solvation, which is often relevant when preparing peptide standards, mechanistic probes, or analogs for binding and stability studies. The defined (2R,3R) stereochemistry supports reliable incorporation into synthetic sequences, while the hydroxyl group provides an additional functional handle for later steps such as selective protection, derivatization, or compatibility with orthogonal chemistry during segment assembly.
3. Pharmaceutical Intermediate Development
(2R,3R)-2-amino-3-hydroxy-4-methyl-valeric acid is also applied as a chiral intermediate in the development of pharmaceutical intermediates and advanced synthetic targets that require a stereodefined amino alcohol motif. Process and synthesis teams value such building blocks when the downstream route benefits from carrying forward the oxygenated stereocenter rather than introducing it later under less controlled conditions. The combination of an amino group and a secondary hydroxyl supports flexible conversion into a range of downstream derivatives used in medicinal chemistry pipelines, including scaffolds where the hydroxyl functionality must be retained for physicochemical tuning or for enabling subsequent functional group transformations.
4. Chemical Biology Probe Analogues
(2R,3R)-2-amino-3-hydroxy-4-methyl-valeric acid is used to generate probe analogues and functionalized peptide-like reagents for chemical biology studies that require a hydroxyl-containing stereocenter within the recognition element. In practice, researchers incorporate this building block into probe scaffolds to maintain the intended hydrogen-bonding and stereochemical features while appending other tags or reactive groups elsewhere in the molecule. The secondary alcohol provides a practical site for controlled derivatization during probe construction, helping teams tailor solubility and reactivity without disturbing the stereochemical integrity of the core residue.
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