D-δ-Hydroxynorvaline is a D-configured, non-proteinogenic amino acid featuring a three-carbon side chain terminated by a hydroxyl group (δ-hydroxy substitution) and bearing both an amino group and a carboxyl group suitable for peptide-related chemistry. The molecule's stereochemistry is specified as D, and the side-chain alcohol provides a hydrogen-bonding and polarity-modulating functionality while the amino and carboxyl groups can participate in salt formation, derivatization, or coupling reactions to form amide linkages. In synthesis and chemical biology workflows, it is used as a building block for preparing modified peptides, for structure-activity studies where δ-hydroxy functionality is required, and for analytical or labeling applications that benefit from an alcohol-containing amino acid side chain.
CAT No: CP07503
D-δ-Hydroxynorvaline is a D-configured amino acid featuring a branched aliphatic side chain terminating in a δ-hydroxyl group, along with a primary amino functionality and a carboxylic acid (or corresponding salt/derivative depending on formulation). The stereogenic center at the α-carbon provides defined chiral control for downstream peptide coupling and for stereospecific recognition in biochemical assays. The side-chain hydroxyl can participate in hydrogen bonding and can be selectively protected or activated to support controlled functionalization. As a chiral amino acid intermediate, D-δ-Hydroxynorvaline can be incorporated into protected amino acid derivatives for peptide building block preparation and can also serve as a precursor for further transformations of the hydroxyl-bearing side chain.
1. Peptide Synthesis
D-δ-Hydroxynorvaline supports peptide building block preparation in peptide synthesis workflows where a D-amino acid with a protected side-chain hydroxyl is required for controlled coupling and stereochemical fidelity. The amino acid backbone enables standard amide bond formation after conversion to an N-protected form, while the δ-hydroxyl can be orthogonally protected to prevent side reactions during coupling and subsequent deprotection steps. Incorporation into short peptides or longer peptide segments can be used to tune conformational preferences and hydrogen-bonding patterns through the side-chain hydroxyl. The resulting D-hydroxylated peptide analogs can be used for structure-activity relationship studies, peptide library construction, and method development in peptide coupling chemistry.
2. Peptidomimetics And SAR
D-δ-Hydroxynorvaline is suitable for peptidomimetic construction where a D-configured hydroxyl-bearing side chain helps model polar interactions and stereochemical constraints in bioactive scaffolds. The δ-hydroxyl group can be maintained as a hydrogen-bond donor/acceptor or converted into protected/activated derivatives that later enable side-chain diversification, supporting systematic SAR studies. The D-configuration at the α-carbon can be used to probe stereochemical effects on target binding or proteolytic stability in peptide-like structures without changing the polar functionality. Downstream derivatives prepared from this amino acid can feed into fragment-based molecular design and iterative medicinal chemistry campaigns focused on amino acid side-chain geometry.
3. Chemical Biology Labels
D-δ-Hydroxynorvaline can be applied in chemical biology research for biomolecule modification strategies that rely on a functional side-chain hydroxyl for conjugation handle installation. The δ-hydroxyl enables derivatization to activated ester, carbonate, or ether-forming intermediates, while the amino acid backbone can be protected to allow selective functional group transformations without uncontrolled crosslinking. D-amino acid incorporation can also be used to generate more stable peptide or protein fragments that retain defined stereochemistry during labeling experiments. Labeled conjugates derived from this compound may serve as probes for binding studies, interaction mapping, and analytical tracking of peptide or protein constructs.
4. Side-Chain Functionalization
D-δ-Hydroxynorvaline is relevant to synthetic organic chemistry as a chiral amino acid intermediate for side-chain functionalization routes that begin from the δ-hydroxyl group. The side-chain hydroxyl can be protected for chemoselective manipulations, then activated or transformed into ethers, esters, or other oxygen-functional motifs that remain compatible with peptide coupling conditions. The presence of a defined chiral center supports stereochemical retention or controlled stereochemical outcomes in subsequent transformations, making it useful for generating stereopure hydroxylated analogs. Downstream products can function as intermediates for fine chemical synthesis, including hydroxyl-rich chiral building blocks used in multi-step manufacturing sequences.
5. Pharmaceutical Manufacturing Intermediates
D-δ-Hydroxynorvaline can be used as a process chemistry intermediate in the preparation of protected amino acid derivatives destined for peptide-like active ingredients or process-scale synthesis of stereopure intermediates. The amino acid functionality supports conversion to N-protected forms suitable for controlled coupling, while the δ-hydroxyl can be managed through protecting-group strategies that align with industrial deprotection and purification constraints. The D-configuration provides a defined stereochemical identity that is important for reproducible manufacturing of chiral building blocks used in downstream assembly. Industrial workflows can employ this compound to generate consistent peptide coupling inputs, enabling scalable synthesis of D-hydroxylated amino acid segments and their derivatives.
6. Analytical Research Standards
D-δ-Hydroxynorvaline can be employed in analytical research for the development of stereochemically defined standards and reference materials used in amino acid profiling and peptide hydrolysate characterization. The combination of a D-configured α-center and a δ-hydroxyl side chain creates a distinctive chemical signature that can aid chromatographic separation and mass-based identification when compared with L-counterparts or non-hydroxyl analogs. Protected derivatives derived from this amino acid can serve as internal standards or calibration components for methods that monitor amino acid composition, stereochemical integrity, or side-chain modifications in peptide synthesis and processing. Analytical utilization of this compound supports quality control and method verification in applied peptide chemistry and industrial chemical manufacturing contexts.
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