D-Isovaline is the D-stereoisomer of the branched-chain amino acid isovaline, featuring an α-amino group and a carboxyl group attached to a secondary carbon bearing a hydrophobic isopropyl side chain. The molecule contains the free amino and carboxyl functional groups characteristic of amino acids, with stereochemistry specified as the D form at the α-carbon and no additional side-chain functionalization beyond the alkyl substituent. D-Isovaline is used in peptide chemistry and structure-activity or stereochemical studies where incorporation of a stereodefined, non-identical-to-protein stereoisomer of a branched amino acid is required, as well as in analytical method development and isotopic or stereochemical differentiation experiments.
CAT No: CP07603
D-Isovaline is the D-enantiomer of the isopropyl-substituted amino acid (2-amino-3-methylbutanoic acid), featuring a single stereogenic center at the α-carbon and a secondary aliphatic side chain that can participate in hydrophobic interactions and steric tuning. The molecule contains a primary amino group and a carboxylic acid, enabling standard amino acid coupling chemistry while also allowing conversion into protected amino acid derivatives for controlled peptide assembly. D-Isovaline's stereochemical inversion relative to L-isovaline makes it suitable for enantioselective studies, racemate resolution workflows, and the construction of D-amino acid-containing peptide motifs. The presence of an unprotected amino acid functionality also makes it a practical feedstock for downstream derivatization to esters, amides, and N-protected intermediates used in fine chemical and biochemical research.
1. Peptide Synthesis
D-Isovaline is applied in peptide synthesis workflows where incorporation of D-amino acid residues supports access to stereochemically defined peptide analogs and protease-resistance studies. The α-amino and α-carboxyl functional groups enable conversion to N-protected amino acid derivatives and C-terminal activation states compatible with peptide coupling reagents. Side-chain branching from the isopropyl group can influence coupling outcomes and conformational preferences, supporting structure-activity relationship studies that probe hydrophobic and steric contributions. D-Isovaline-derived building blocks can be used to prepare D-amino acid-containing sequences for peptide science, synthetic methodology development, and downstream analog generation.
2. Chiral Building Blocks
D-Isovaline is used as a chiral amino acid intermediate in stereoselective synthesis and enantiopure chemical manufacturing, leveraging its defined D-configuration at the α-carbon. The amino acid backbone supports protection-group strategies such as N-Boc or N-Cbz formation and esterification of the carboxyl group to control chemoselectivity during sequential transformations. The branched isopropyl side chain provides a sterically informative handle for constructing chiral derivatives that can serve as intermediates to other stereogenic scaffolds. D-Isovaline can therefore function as a practical starting material for chiral derivatization, asymmetric synthesis planning, and preparation of downstream enantiopure amino acid derivatives.
3. Amino Acid Derivatization
D-Isovaline is suitable for amino acid derivatization in chemical research and specialty intermediate production, where conversion of the free amino acid into esters, amides, or activated carboxyl derivatives enables broad downstream reactivity. The primary amine can be selectively protected to avoid side reactions during functional group transformations, while the carboxylic acid can be transformed into coupling-ready intermediates for subsequent bond formation. The hydrophobic isopropyl side chain supports formation of lipophilic derivatives used in analytical standards, reagent development, and synthetic intermediate libraries. D-Isovaline-based derivatives can be employed to generate labeled or functionalized amino acid analogs for mechanistic studies and applied chemical synthesis.
4. Chemical Biology Research
D-Isovaline is applied in chemical biology research contexts that require D-amino acid incorporation for probing peptide recognition, stability, and conformational effects in biomolecular systems. The D-stereocenter and side-chain hydrophobicity support design of peptide mimetics and peptidomimetic fragments used to investigate binding-site preferences and stereochemical constraints. The amino acid's functional groups enable preparation of conjugation-ready intermediates, including N-protected forms that can be deprotected or activated for attachment to biomolecular scaffolds. D-Isovaline thus serves as a stereochemically defined input for biochemical research intermediate generation and molecular recognition studies.
5. Pharmaceutical Intermediate Preparation
D-Isovaline is used in pharmaceutical intermediate preparation as a chiral building block for constructing amino acid-derived fragments and D-amino acid motifs within synthetic routes. The amino acid functionality supports manufacturing-compatible protection and activation strategies, including N-protection and conversion of the carboxyl group into activated esters or coupling partners for subsequent assembly steps. The branched aliphatic side chain can be translated into hydrophobic substituent patterns within larger drug-like scaffolds and peptidomimetic structures. D-Isovaline-derived intermediates can be incorporated into fine chemical synthesis planning where stereochemical fidelity and controlled functional group interconversions are required.
6. Analytical Standards Development
D-Isovaline is utilized in analytical research for developing enantiomerically defined standards and calibration materials for amino acid profiling and stereochemical assays. The D-configuration at the α-carbon enables discrimination from L-isovaline in chiral chromatography or derivatization-based analytical workflows. The amino acid's functional groups allow conversion into stable derivatives that can improve detectability and facilitate method transfer across instrumentation platforms. D-Isovaline therefore supports robust analytical method development, quality control of amino acid derivative streams, and stereochemical verification in applied chemical research.
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