N-α-Benzyl-O-tert.butyl-L-serine methyl ester hydrochloride is a protected serine derivative featuring a serine amino acid backbone bearing an N-α benzyl group and an O-tert-butyl ether on the side-chain hydroxyl, with a methyl ester at the carboxyl terminus. The molecule is present as a hydrochloride salt, and it contains an N-substituted amide-forming nitrogen (no free amino group) alongside a methyl ester carbonyl and a tert-butyl-protected hydroxyl that modulates polarity and chemoselectivity while the L stereochemistry is specified in the name. In peptide and amino acid derivative synthesis, this protected amino acid ester functions as a stepwise building block whose protected side-chain and carboxyl ester enable controlled coupling and subsequent deprotection strategies for generating serine-containing peptide intermediates or labeled/functionalized serine derivatives.
CAT No: CP01817
N-α-Benzyl-O-tert.butyl-L-serine methyl ester hydrochloride is a chiral L-serine derivative presented as a methyl ester hydrochloride, combining a protected hydroxyl functionality with an N-protecting benzyl group. The serine side chain bears an O-tert-butyl ether that suppresses hydroxyl reactivity during peptide coupling and selective downstream transformations, while the α-amino group is rendered less nucleophilic by N-benzyl protection. The methyl ester and hydrochloride counterion provide a defined, isolable form for controlled acylation chemistry and for later conversion to carboxylic acid or peptide-ready formats. The stereogenic center at the serine α-carbon supports stereochemically consistent peptide building block preparation, and the benzyl and tert-butyl groups enable orthogonal deprotection strategies that are compatible with protected amino acid synthesis workflows.
1. Peptide Synthesis
N-α-Benzyl-O-tert.butyl-L-serine methyl ester hydrochloride is applied in peptide building block preparation where the protected serine side-chain hydroxyl (O-tert-butyl) prevents side reactions during amide bond formation. The N-benzyl protection and methyl ester form a controlled substrate for coupling chemistry, supporting incorporation of the L-serine residue into protected peptide chains with minimal interference from the side-chain alcohol. Orthogonal deprotection of the O-tert-butyl group can be scheduled after peptide assembly to enable subsequent side-chain functionalization or native serine presentation. Downstream peptide analog construction benefits from the defined stereochemistry and ester handle, which can be converted to carboxylate-based intermediates for continued chain elongation.
2. Amino Acid Derivatization
N-α-Benzyl-O-tert.butyl-L-serine methyl ester hydrochloride supports amino acid derivatization programs that require selective manipulation of the serine hydroxyl without disturbing the peptide-compatible backbone. The O-tert-butyl ether acts as a protecting group that can be removed under conditions that preserve the N-benzyl functionality, enabling controlled generation of a free side-chain alcohol for etherification, esterification, or further conversion to leaving-group derivatives. The methyl ester hydrochloride format can participate in acyl transfer or be hydrolyzed to access carboxylic acid derivatives for subsequent coupling or conjugation. The resulting serine-based intermediates can be used to build stereochemically defined side-chain variants for structure-activity relationship studies and synthetic methodology development.
3. Protected Amino Acid Chemistry
N-α-Benzyl-O-tert.butyl-L-serine methyl ester hydrochloride is suited to protected amino acid synthesis and intermediate preparation where orthogonal protection is a key process-design element. The combination of N-benzyl and O-tert-butyl protection provides a protection pattern that can be leveraged to manage chemoselectivity across sequential steps, including peptide coupling, protecting-group exchange, and late-stage functionalization. The hydrochloride salt form improves handling and can facilitate reproducible substrate dosing in solid or solution-phase workflows used for fine chemical synthesis. The chiral L-serine core ensures stereochemical fidelity through transformations that may involve ester activation, N-deprotection, or side-chain unmasking to generate peptide-ready or conjugation-ready derivatives.
4. Bioconjugation Chemistry
N-α-Benzyl-O-tert.butyl-L-serine methyl ester hydrochloride can be used in bioconjugation chemistry pipelines that require controlled introduction of serine-derived linkers onto biomolecule scaffolds. The protected side-chain hydroxyl enables temporary masking during synthesis of linker fragments, while later deprotection can generate an alcohol handle for formation of activated esters, carbonate linkers, or other conjugation-compatible moieties. The methyl ester can serve as a precursor to carboxylate-containing intermediates that participate in coupling reactions to biomolecule-reactive groups under standard amide or ester-forming strategies. The stereodefined serine residue supports the preparation of well-defined conjugation reagents used for chemical biology studies and analytical reagent generation.
5. Pharmaceutical Manufacturing
N-α-Benzyl-O-tert.butyl-L-serine methyl ester hydrochloride is applicable to pharmaceutical manufacturing contexts involving peptide or peptidomimetic intermediate production where robust protection-group strategy and reproducible chiral building blocks are required. The N-benzyl and O-tert-butyl protections support process-compatible sequencing by reducing undesired nucleophilicity of the amino and hydroxyl functionalities during coupling and intermediate handling. The methyl ester hydrochloride form aligns with manufacturing workflows that convert ester intermediates into carboxylic acid or activated acyl forms for downstream assembly steps. The compound's structured protecting-group pattern can be incorporated into controlled manufacturing routes for serine-containing sequences and for generating defined stereochemical fragments used in specialty chemical production.
6. Process Chemistry Intermediate
N-α-Benzyl-O-tert.butyl-L-serine methyl ester hydrochloride serves as a process chemistry intermediate for scalable synthesis of protected serine derivatives and downstream functional building blocks. The orthogonally protected N- and O-functionalities enable stepwise transformation planning, where side-chain unmasking and backbone activation can be scheduled to minimize cross-reactivity and simplify purification logic. The methyl ester provides a manipulable carbonyl functionality that can be converted into activated intermediates for further coupling or into carboxylic acid derivatives for salt formation and formulation-adjacent handling. The defined L-configuration at the serine α-carbon supports stereochemically consistent intermediate generation for industrial biocatalysis-adjacent workflows and fine chemical synthesis programs requiring predictable amino acid chemistry.
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