H-L-Ser(tBu)-OtBu*HCl

H-L-Ser(tBu)-OtBu*HCl is an L-serine-derived amino acid ester hydrochloride in which the side-chain hydroxyl is protected as a tert-butyl ether (Ser(tBu)) and the carboxyl group is masked as a tert-butyl ester (OtBu), with the overall material present as the hydrochloride salt. The molecule retains the L-configuration at the α-carbon, providing a stereochemically defined chiral center for peptide coupling chemistry and downstream stereospecific transformations. The tert-butyl-protected hydroxyl and carboxyl functionalities exhibit acid-labile protecting-group behavior, while the esterified carboxyl and etherified side chain reduce undesired side reactions during amide bond formation. The salt form improves handling of the amino functionality and supports its use as a protected amino acid intermediate in synthetic organic chemistry and peptide building-block workflows.

1. Protected Amino Acids

H-L-Ser(tBu)-OtBu*HCl is applied in protected amino acid synthesis and intermediate preparation where orthogonal protection of serine is required for controlled derivatization. The α-amino functionality and the tert-butyl-protected carboxyl ester enable peptide coupling compatibility while the Ser(tBu) side-chain ether suppresses hydroxyl reactivity during activation and acylation steps. Acid-triggered deprotection strategies can regenerate the free serine hydroxyl and carboxylic acid forms for subsequent functional group transformations or for conversion into activated peptide coupling derivatives. The hydrochloride salt form supports consistent handling of the amine during manufacturing-scale protected amino acid processing and fine chemical synthesis.

2. Peptide Synthesis

H-L-Ser(tBu)-OtBu*HCl serves as a serine-containing peptide building block in solid-phase or solution-phase peptide synthesis workflows that require temporary protection of both the side-chain hydroxyl and the C-terminus. The tert-butyl ester (OtBu) and tert-butyl ether (tBu) protect groups are structurally aligned with peptide coupling strategies that minimize side reactions from the serine hydroxyl during amide bond formation. L stereochemistry at the α-carbon supports incorporation into peptide sequences with stereochemical fidelity, enabling construction of defined peptide analogs and sequence-specific serine positions. Downstream deprotection can expose the serine hydroxyl for phosphorylation-mimetic chemistry, glycosylation handles, or further side-chain functionalization after peptide assembly.

3. Side-Chain Functionalization

H-L-Ser(tBu)-OtBu*HCl is used for side-chain functionalization routes targeting hydroxyl-bearing serine derivatives and serine-based chemical probes. The protected serine hydroxyl (Ser(tBu)) allows controlled deprotection to generate a free alcohol for subsequent derivatization into reactive intermediates such as leaving-group derivatives, ester-linked conjugation partners, or protected hydroxyl motifs suitable for orthogonal chemistry. The tert-butyl protecting groups can be removed under conditions compatible with many peptide and protecting-group sets, enabling sequential functional group installation without premature cross-reactivity. The resulting serine hydroxyl-bearing intermediates can be carried into peptidomimetic construction, biochemical reagent synthesis, and structure-activity relationship studies requiring defined serine substitution patterns.

4. Chemical Biology Probes

H-L-Ser(tBu)-OtBu*HCl is suitable for chemical biology applications that require incorporation of stereodefined serine residues into labeled peptides, affinity probes, or enzyme-interaction scaffolds. The protected hydroxyl and ester functionalities support assembly of peptide fragments that can later be converted into conjugation-ready alcohol or carboxyl forms for attachment of tags, linkers, or capture moieties. L-configuration ensures consistent spatial presentation of the serine side chain, which can influence molecular recognition in biochemical assay contexts and enable reproducible probe libraries. The compound's protected amino acid form also supports scalable intermediate generation for fragment-based molecular design and downstream probe optimization.

5. Pharmaceutical Intermediate Preparation

H-L-Ser(tBu)-OtBu*HCl is employed in pharmaceutical intermediate preparation and process chemistry for constructing serine-containing fragments with controlled functional group protection during multi-step synthesis. The tert-butyl ester and tert-butyl ether protect groups help manage chemoselectivity by masking the carboxyl and hydroxyl during transformations that require stable handling of the amino acid core. Hydrochloride salt formation can facilitate consistent salt-based processing and feedstock handling in industrial fine chemical production, while the L stereocenter supports stereospecific downstream incorporation into larger intermediates. Deprotection and conversion of the liberated functional groups can yield downstream building blocks used to assemble peptide-like structures, peptidomimetics, and serine-functionalized intermediates for manufacturing-oriented synthetic routes.

1. An Isolated TCR αβ Restricted by HLA-A* 02: 01/CT37 Peptide Redirecting CD8+ T Cells to Kill and Secrete IFN-γ in Response to Lung Adenocarcinoma Cell Lines

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

3. Multifunctional peptide-oligonucleotide conjugate promoted sensitive electrochemical biosensing of cardiac troponin I

4. Genetic, cellular, and structural characterization of the membrane potential-dependent cell-penetrating peptide translocation pore

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