D-Homotyrosine.HBr is a D-configured, non-proteinogenic amino acid derivative featuring a phenolic aromatic side chain extended by one methylene relative to tyrosine (homotyrosine), with an amino group and a carboxyl group on the α-carbon. The molecule is present as a hydrobromide salt, pairing the basic amino functionality with bromide while retaining the phenolic hydroxyl for hydrogen-bonding and electrophile-compatible derivatization chemistry. As a labeled or substituted aromatic amino acid building block, D-Homotyrosine.HBr is used in peptide and amide synthesis workflows and in structure-activity or chemical biology studies where an extended phenolic side chain and defined stereochemistry are required for controlled incorporation into larger molecular frameworks.
CAT No: CP18603
D-Homotyrosine.HBr is a chiral, side-chain-extended amino acid salt in which the homotyrosine framework retains the phenolic aromatic ring characteristic of tyrosine while introducing an additional methylene unit for altered steric and conformational behavior. The molecule exists as the hydrobromide form, pairing the amino functionality with bromide and thereby increasing handling stability and water compatibility relative to the free base. The stereogenic center at the amino acid carbon provides defined chirality for incorporation into peptide-like structures, while the phenolic hydroxyl enables selective protection, derivatization, and post-coupling functional group transformations. The combination of an amino acid backbone, a phenolic handle, and salt-state reactivity makes D-homotyrosine.HBr a practical chiral intermediate for amino acid derivatization and protected amino acid synthesis.
1. Peptide Synthesis
D-Homotyrosine.HBr supports peptide building-block workflows in solid-phase or solution-phase peptide synthesis by providing a chiral amino acid precursor whose side-chain phenol can be protected prior to coupling. The hydrobromide salt form can be converted to the corresponding free amine under controlled conditions to enable standard amide bond formation at the amino group while maintaining stereochemical integrity at the D-center. Side-chain protection strategies such as phenolic ether or carbonate protection can be applied to prevent undesired O-acylation during peptide coupling and to allow orthogonal deprotection after chain assembly. Downstream, D-homotyrosine-containing peptides and peptidomimetics can be generated for scaffold diversification, backbone/side-chain spacing studies, and enzymatic recognition mapping.
2. Side-Chain Functionalization
D-Homotyrosine.HBr enables side-chain functionalization chemistry through the phenolic hydroxyl, which can be selectively protected, activated, and transformed into reactive intermediates for conjugation or further synthetic elaboration. The extra methylene spacer relative to tyrosine can influence positioning of the aromatic/phenolic group in derivatized products, which is relevant for designing linkers and sterically tuned analogs. Hydrobromide salt handling supports consistent downstream conversion into protected amino acid derivatives that participate in O-alkylation, O-acylation, or electrophile-mediated phenol functional group installation. Resulting D-homotyrosine derivatives can be used to generate functionalized amino acid analogs for chemical biology probes, receptor-binding fragment optimization, and peptidomimetic construction where aromatic positioning is a design variable.
3. Chiral Amino Acid Intermediate
D-Homotyrosine.HBr serves as a chiral amino acid intermediate for stereodefined synthesis routes that require D-configuration at the amino acid center. The presence of both an amino acid functionality and a phenolic group allows staged protection-group strategies, where salt-state management and selective phenol protection can be orchestrated to control chemoselectivity during conversion to activated esters, protected amines, or coupling-ready derivatives. The D stereochemistry can be retained through standard protection and activation sequences, supporting the preparation of enantiopure building blocks for unnatural amino acid incorporation. Downstream utility includes manufacturing of research-grade peptide components, chiral derivatization reagents, and intermediate streams used to construct stereochemically defined peptidomimetics and amino acid-based scaffolds.
4. Chemical Biology Probes
D-Homotyrosine.HBr is applicable to chemical biology research where aromatic phenol-containing amino acid analogs are used to probe molecular recognition, binding-site geometry, and structure-function relationships. The phenolic hydroxyl provides a handle for installing affinity tags, photoactivatable groups, or clickable moieties after appropriate protection and functional group activation. The D-homotyrosine stereocenter can be incorporated into peptide analogs to modulate protease stability and to distinguish stereospecific interactions in binding assays without requiring a change in aromatic chemistry. Resulting labeled or functionalized D-homotyrosine-containing constructs can be employed as biochemical research intermediates for target engagement studies, enzyme-substrate analog design, and molecular recognition mapping.
5. Pharmaceutical Intermediate Preparation
D-Homotyrosine.HBr can be utilized in pharmaceutical intermediate preparation for the synthesis of D-amino acid-containing fragments and peptide-like compounds used in medicinal chemistry programs. The amino acid backbone supports conversion into protected amino acid derivatives compatible with coupling chemistry, while the phenolic group can be managed via orthogonal protection to align with multi-step synthesis planning. Hydrobromide salt formation improves reproducibility of handling and can facilitate controlled conversion to coupling-ready forms that feed into fragment assembly, SAR-focused analog generation, and peptidomimetic construction. Downstream, D-homotyrosine-derived intermediates can be directed toward specialty chemical production of stereochemically defined building blocks used in iterative structure optimization workflows.
6. Process Chemistry Manufacture
D-Homotyrosine.HBr is suitable for process chemistry and fine chemical synthesis routes that benefit from salt-state control and functional group orthogonality during manufacturing. The hydrobromide form provides a defined ionic state that can improve material handling and enable predictable downstream transformations into protected amino acid derivatives for coupling or derivatization steps. The combination of an amino group and a phenolic hydroxyl supports chemoselective protection/deprotection sequences that can be integrated into scalable process designs, including preparation of coupling intermediates and side-chain-modified outputs. Resulting D-homotyrosine-based streams can serve as industrial chemical manufacturing intermediates for peptide building blocks, chiral amino acid derivatives, and functionalized aromatic amino acid products used across applied chemical synthesis.
1. The spatiotemporal control of signalling and trafficking of the GLP-1R
2. Cell-based adhesion assays for isolation of snake venom’s integrin antagonists
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