Erythro-DL-β-Hydroxynorvaline is a non-proteinogenic β-hydroxy amino acid derivative of norvaline featuring a five-carbon side chain bearing a secondary hydroxyl group at the β-position. The molecule contains a free amino group and a free carboxyl group, and its erythro stereochemical relationship between the β-hydroxyl substituent and the amino-bearing carbon is specified while the overall DL designation indicates a racemic mixture of enantiomeric forms. In peptide chemistry and chemical biology, β-hydroxy amino acids like this one are used as structural building blocks to introduce hydroxyl functionality for hydrogen-bonding and for generating defined stereochemical elements in peptide analogues, as well as for structure-activity and site-specific modification studies.
CAT No: CP07402
Erythro-DL-β-Hydroxynorvaline is a DL mixture of the erythro diastereomeric relationship at the β-hydroxy-bearing stereocenter of a norvaline-derived amino acid framework, providing a chiral amino acid intermediate with a β-hydroxyl functional group and a primary amino group. The molecule contains the amino acid backbone motif (carboxylic acid and amino functionality) that supports standard peptide coupling chemistry after conversion to appropriate protected forms. The β-hydroxyl group can participate in esterification, ether formation, or selective oxidation/reduction chemistry, enabling side-chain functionalization and downstream derivatization. As a stereodefined amino acid building block precursor, it can be incorporated into peptide analogs or used to prepare protected amino acid derivatives that control reactivity during synthesis and subsequent deprotection.
1. Peptide Synthesis
Erythro-DL-β-Hydroxynorvaline is applied in peptide synthesis workflows where a β-hydroxy side chain is required for amide bond formation and subsequent hydroxyl-directed transformations. The amino acid backbone supports conversion to N-protected, carboxyl-activated coupling partners, while the β-hydroxyl group can be protected or selectively left to tune chemoselectivity during peptide assembly. Erythro stereochemical relationship at the β-carbon can be leveraged when generating hydroxy-containing peptide fragments and peptidomimetic turn elements that require controlled stereochemical presentation. Downstream peptide analog construction can use the hydroxyl handle for further derivatization, including ester/ether formation or conjugation-ready functional group generation, aligning the building block with peptide science and synthetic methodology development.
2. Amino Acid Derivatization
Erythro-DL-β-Hydroxynorvaline is suitable for amino acid derivatization programs targeting side-chain functional group diversification from a β-hydroxy motif. The β-hydroxyl enables formation of protected esters or ethers, allowing orthogonal protection strategies when preparing complex amino acid derivatives for multi-step synthesis. The carboxylic acid and amino group can be transformed into activated intermediates, such as protected amino acid esters or coupling-ready derivatives, to support controlled reactivity in downstream synthetic organic chemistry. The resulting functionalized amino acid derivatives can serve as intermediates for library synthesis, stereochemical studies, and conversion into specialized building blocks used in peptide analogs and biochemical probe preparation.
3. Chiral Building Block Preparation
Erythro-DL-β-Hydroxynorvaline is used as a chiral amino acid intermediate in stereochemical research and process-oriented preparation of β-hydroxy-containing scaffolds. The erythro stereochemical relationship at the β-carbon, combined with the amino acid functional groups, supports systematic protection-group selection for N- and O-functionalities to manage stereochemical integrity through coupling and deprotection steps. The DL nature can be employed in comparative studies of stereochemical outcomes or in manufacturing routes where racemic intermediates are acceptable before resolution or stereoselective downstream transformations. Conversion into protected amino acid derivatives, such as N-protected forms with hydroxyl protection, can enable consistent handling as a chiral precursor for further stereochemical elaboration in fine chemical synthesis.
4. Peptidomimetics And SAR Studies
Erythro-DL-β-Hydroxynorvaline is applied in peptidomimetic construction and structure-activity relationship studies where β-hydroxy side chains influence conformational preferences and hydrogen-bonding patterns. The amino acid backbone allows incorporation into peptide-like frameworks, while the β-hydroxyl group provides a polar handle for tuning intermolecular interactions and for generating additional functional groups through controlled derivatization. Protected amino acid synthesis strategies can maintain orthogonality between the hydroxyl and amino functionalities, supporting sequential elaboration of analog series without cross-reactivity. The resulting hydroxy-containing analogs can be used as molecular design inputs for SAR investigations and for building stereochemically characterized libraries that probe how side-chain stereochemistry and functionality affect binding-relevant properties.
5. Bioconjugation And Chemical Biology
Erythro-DL-β-Hydroxynorvaline is utilized in chemical biology and bioconjugation contexts where a β-hydroxy-containing amino acid motif is needed for linker or probe construction. The hydroxyl group can be converted into functionalized handles such as activated esters, ether-linked moieties, or oxidation-state-adjusted derivatives that participate in conjugation chemistry while maintaining an amino acid-derived stereochemical element. N- and C-terminal functionalization of protected derivatives can enable attachment strategies compatible with peptide-based targeting vectors and labeling reagents. Downstream formation of conjugatable intermediates supports the generation of biomolecule-modified constructs and analytical standards used to study structure-function relationships in amino acid and peptide systems.
6. Pharmaceutical Intermediate Preparation
Erythro-DL-β-Hydroxynorvaline is relevant to pharmaceutical intermediate preparation and process chemistry for manufacturing routes that require β-hydroxy amino acid building blocks. The amino acid functionality supports conversion into protected, coupling-compatible derivatives that can be carried through multi-step synthesis with controlled chemoselectivity, including hydroxyl protection to prevent undesired side reactions. Carboxyl activation and N-protection strategies enable integration into larger synthetic sequences, including fragment coupling toward peptide-like intermediates and stereochemically defined side-chain motifs. Industrially, the β-hydroxyl group provides a downstream transformation point for forming esters, ethers, or other oxygenated functionalities that can be carried into final synthetic targets or used to generate intermediate families for specialty chemical production.
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