D-Valine is the D-stereoisomer of the proteinogenic amino acid valine, featuring an aliphatic isopropyl side chain and a branched hydrophobic character. The molecule contains a free amino group and a free carboxyl group, enabling it to exist as a zwitterion in aqueous conditions, and its stereochemistry is defined by the D configuration at the alpha carbon. D-Valine is used as a substrate and building block in peptide and amino acid derivative synthesis, as well as in analytical and labeling workflows where stereochemically defined, non-L amino acid inputs are required.
CAT No: CP02201
CAS No:640-68-6
Synonyms/Alias:6404-31-5;N-Benzyloxycarbonyl-D-proline;Z-D-Pro-OH;N-Cbz-D-proline;Cbz-D-Pro-OH;(R)-1-((Benzyloxy)carbonyl)pyrrolidine-2-carboxylicacid;(+)-Z-D-proline;1-[(benzyloxy)carbonyl]-d-proline;(R)-N-BENZYLOXYCARBONYLPROLINE;CBZ-D-PROLINE;N-Carbobenzoxy-D-proline;(2R)-1-[(benzyloxy)carbonyl]pyrrolidine-2-carboxylicacid;(+)-CARBOBENZYLOXY-D-PROLINE;MFCD00063228;(+)-N-CARBOBENZYLOXY-D-PROLINE;(R)-1-(BENZYLOXYCARBONYL)PYRROLIDINE-2-CARBOXYLICACID;D-Proline,N-CBZprotected;(2R)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylicacid;1,2-PYRROLIDINEDICARBOXYLICACID,1-(PHENYLMETHYL)ESTER,(2R)-;PubChem10516;Z-D-PROLINE;D-Z-PRO;N-CBZ-D-PRO-OH;benzyloxycarbonyl-D-proline;AC1Q5QW9
D-Valine is the D-enantiomer of the branched-chain amino acid valine, featuring a stereogenic α-carbon that bears an amino group, a carboxylic acid, and an isopropyl side chain. The molecule's zwitterionic form under aqueous conditions and its primary amine and carboxyl functionality make it a direct participant in amino acid derivatization and peptide coupling chemistry. D-Valine's chiral nature enables stereochemically defined incorporation into peptide segments, while its aliphatic side chain supports downstream transformations such as side-chain functionalization to introduce hydrophobic or sterically tuned motifs. As a chiral amino acid building block, D-Valine can be converted into protected amino acid derivatives, enabling controlled N- and/or C-terminal strategies that preserve stereochemical integrity during synthesis.
1. Peptide Synthesis
D-Valine is applied in peptide synthesis workflows where stereodefined incorporation of the D-configured residue is required for conformational control and protease resistance studies. The amino and carboxyl groups support standard peptide coupling chemistry after conversion to an appropriate protected amino acid derivative, enabling selective N-acylation while maintaining compatibility with common protecting-group schemes. The isopropyl side chain contributes hydrophobic character and steric bulk that can influence folding propensity in peptide analogs and peptidomimetics. D-Valine-based building blocks can therefore be used to construct D-amino acid containing peptides for structure-function investigations and synthetic scaffold generation in amino acid chemistry.
2. Chiral Building Blocks
D-Valine functions as a chiral amino acid intermediate for stereoselective synthesis of downstream enantiopure targets, including chiral amide, ester, and nitrile derivatives derived from its carboxyl and amino functionalities. The D-stereocenter provides a fixed stereochemical handle that can be retained through protection, activation, and coupling steps, supporting reproducible stereochemical outcomes in fine chemical synthesis. Conversion to N-protected forms and optional C-terminal esterification can facilitate isolation and controlled reactivity during multistep routes. D-Valine thus serves as a practical chiral precursor for producing stereodefined intermediates used in chemical manufacturing and research-grade synthesis.
3. Chemical Biology Labeling
D-Valine is utilized in chemical biology and analytical research to generate stereochemically defined amino acid analogs for labeling, tracer preparation, and binding studies involving D-amino acid motifs. The primary amino group enables derivatization to amide, urea, or sulfonamide linkages, while the carboxylic acid can be activated for conjugation to probes or immobilization supports. The branched hydrophobic side chain can be leveraged to tune local interactions in peptide-based probes and biomolecule interaction assays. D-Valine-derived conjugates can be employed to support molecular recognition studies, biomolecule modification strategies, and reference material preparation for analytical characterization.
4. Peptidomimetics And SAR
D-Valine is applied in peptidomimetic construction and structure-activity relationship studies where D-amino acid incorporation modulates backbone conformation and proteolytic stability of peptide-like scaffolds. The amino acid backbone supports iterative assembly into analogs, while the isopropyl side chain provides a consistent hydrophobic element that can be systematically varied via derivatization of the α-amino and carboxyl termini. Protecting-group strategies that differentiate N- and C-terminal reactivity enable sequential functionalization, supporting SAR workflows that require controlled introduction of functional groups at defined positions. D-Valine-based intermediates can therefore be used to build stereochemically defined libraries and to generate comparative analogs for mechanistic and binding investigations.
5. Pharmaceutical Intermediate Preparation
D-Valine is suitable for pharmaceutical intermediate preparation in process chemistry contexts where enantiopure amino acid derivatives are required as route inputs to active pharmaceutical ingredient fragments or excipient-related components. The functional group set supports conversion to protected amino acid derivatives that participate in coupling, esterification, or amide formation under manufacturing-compatible conditions. The D-configuration can be preserved through N-protection and controlled activation of the carboxyl group, enabling stereodefined downstream synthesis of chiral amide and ester intermediates. D-Valine-derived building blocks can be applied in specialty chemical production where stereochemical fidelity and scalable amino acid chemistry are central to intermediate generation.
6. Side-Chain Functionalization
D-Valine is employed for side-chain functionalization strategies that transform the branched aliphatic motif into chemically distinct handles for further conjugation or scaffold diversification. The inherent reactivity is centered on the α-amino and carboxyl groups, which can be protected to allow selective chemistry on the side chain through multistep derivatization planning. Functionalized D-valine derivatives can then be used to introduce hydrophobicity, steric constraints, or additional functional groups into peptides and peptidomimetics. D-Valine therefore serves as a stereodefined amino acid starting point for generating functionalized intermediates used in synthetic organic chemistry and applied product development.
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