H-alpha-Prg-D-Ala-OH

H-alpha-Prg-D-Ala-OH is a chiral D-alanine derivative in which the alpha-amino group is protected as an N-(2-propyl-2,3,4,5-tetrahydro-1H-benzo[d]azepinyl)carbonyl-type Prg (Prg) protecting group, while the carboxylic acid remains unesterified. The stereogenic center at the alpha carbon is set to the D-configuration, enabling stereochemically defined peptide incorporation and epimerization-sensitive synthetic planning. The molecule presents a protected amide-forming nitrogen and a free carboxyl group that can be activated for peptide coupling or converted into downstream acid derivatives. The Prg protecting group is designed to be compatible with peptide synthesis workflows and can be removed under conditions that preserve the D-configuration, supporting reliable construction of D-Ala-containing sequences and chiral intermediates.

1. Peptide Synthesis

H-alpha-Prg-D-Ala-OH is used as a D-alanine peptide building block for solid-phase or solution-phase peptide coupling where stereochemical fidelity is required. The free carboxylic acid enables activation to form an acylating species, while the Prg-protected amino function participates in standard amide bond formation after deprotection or as dictated by the coupling order. Prg protection supports orthogonal protection strategies that help control which functional group is reactive during stepwise chain assembly. D-configuration at the alpha carbon supports incorporation into peptide segments that require resistance to proteolysis or defined stereochemical motifs, yielding peptide analogs suitable for biochemical research and SAR studies.

2. Amino Acid Derivatization

H-alpha-Prg-D-Ala-OH functions as a chiral amino acid intermediate for derivatization chemistry that targets the carboxyl group and allows controlled transformation of the protected amine. Free acid functionality can be converted into activated esters, amide-forming derivatives, or coupling-ready intermediates for downstream synthesis of labeled or functionalized amino acid derivatives. The Prg-protected nitrogen supports selective reactions that avoid premature amine reactivity, enabling sequential functional group installation on the side of the molecule that remains chemically accessible. D-Ala stereochemistry can be retained through carefully chosen activation and coupling steps, supporting the preparation of enantiomerically defined reagents for peptide construction, chemical biology probes, and synthetic intermediate manufacturing.

3. Chemical Biology Probes

H-alpha-Prg-D-Ala-OH is applied in chemical biology workflows where stereodefined D-amino acid residues are incorporated into probes, reporters, or binding scaffolds. The combination of a protected amine and a free carboxylic acid supports conjugation strategies that generate amide-linked probe constructs without disturbing the D-configuration. Prg protection can be leveraged to manage orthogonal deprotection timing, allowing selective unveiling of reactive sites during probe assembly and subsequent functionalization. Downstream derivatives can be used to study molecular recognition, receptor or enzyme binding preferences, and stereochemical effects on peptide-like interactions in a manner consistent with amino acid chemistry and peptide science.

4. Peptidomimetics And SAR

H-alpha-Prg-D-Ala-OH serves as a stereochemically defined component for peptidomimetic construction and structure-activity relationship studies that require controlled placement of D-alanine. The alpha carboxylic acid supports incorporation into analogs through peptide bond formation, while the Prg-protected amino group supports synthetic sequences that manage protection state across iterative design cycles. D-configuration enables systematic evaluation of stereochemical contributions to binding and stability in peptide mimics, including analogs where protease resistance or conformational bias is a design variable. Synthesized analogs derived from this chiral intermediate can feed SAR workflows and fragment-based optimization efforts by providing consistent stereochemical inputs for comparative studies.

5. Pharmaceutical Intermediate Preparation

H-alpha-Prg-D-Ala-OH is suitable for industrial fine chemical synthesis routes that require chiral amino acid intermediates compatible with peptide-like manufacturing steps. The presence of a protected amine and a free acid supports conversion into coupling-ready forms used in batch or continuous process chemistry for constructing D-Ala-containing intermediates. Prg protection provides a handle for managing reaction selectivity during manufacturing, helping align deprotection and coupling operations with downstream purification and quality control needs. The resulting D-Ala-containing intermediates can be carried into larger synthetic sequences for peptide-derived materials, research-grade reference standards, and specialty chemical production where stereochemical control is a process requirement.

6. Analytical Research Standards

H-alpha-Prg-D-Ala-OH is utilized in analytical research as a chiral reference material and intermediate for method development involving amino acid derivatives and peptide-like compounds. The defined D-stereochemistry and protected functional group pattern support consistent chromatographic and spectroscopic behavior when establishing analytical workflows for protected amino acids, coupling products, or deprotection outcomes. The free carboxylic acid enables conversion to derivatives that match the functional state of analytes encountered during peptide synthesis and purification monitoring. Use of this compound in analytical standard preparation supports reliable identification and quantification of stereochemically defined D-Ala-containing species across biochemical research and applied synthetic chemistry.

1. Urinary Metabolites Associated with Blood Pressure on a Low-or High-Sodium Die

2. Quantitative Analysis of Ligands Effects on Bioefficacy of Nanoemulsion encapsulating Depigmenting Active

3. C-peptide and its C-terminal fragments improve erythrocyte deformability in type 1 diabetes patients

4. An interdomain binding site on HIV-1 Nef interacts with PACS-1 and PACS-2 on endosomes to down-regulate MHC-I

5. Myotropic activity and immunolocalization of selected neuropeptides of the burying beetle Nicrophorus vespilloides (Coleoptera: Silphidae)