Boc-D-Serine methyl ester is a protected amino acid derivative in which the amino group of D-serine is carbamated with a Boc (tert-butoxycarbonyl) protecting group and the carboxyl group is converted to a methyl ester. The molecule retains the serine side chain featuring a primary hydroxymethyl substituent, and the D stereochemistry is specified in the product name, with the Boc group functioning to suppress unprotected amine reactivity while the methyl ester masks the carboxylate. This protected ester is used as a stepwise building block in peptide synthesis workflows and as a controlled substrate for preparing more complex serine-containing amino acid and peptide derivatives, including intermediates that require temporary protection of both the amino and carboxyl functionalities.
CAT No: CP01809
CAS No:95715-85-8
Synonyms/Alias:95715-85-8;BOC-D-Serinemethylester;BOC-D-SER-OME;N-BOC-D-Serinemethylester;(R)-Methyl2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate;methyln-(tert-butoxycarbonyl)-d-serinate;N-(tert-Butoxycarbonyl)-D-serinemethylester;D-Serine,N-[(1,1-dimethylethoxy)carbonyl]-,methylester;methyl(2R)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropanoate;NSC659314;zlchem1160;PubChem10470;AC1Q5XMJ;AC1L8D9D;KSC491O0H;446068_ALDRICH;SCHEMBL3617926;CTK3J1703;ZLD0629;MolPort-004-785-594;SANNKFASHWONFD-ZCFIWIBFSA-N;ACT00016;ZINC1637062;ANW-43778;AR-1J5929
Boc-D-Serine methyl ester is a D-configured serine derivative bearing a Boc-protected amino group and a methyl ester at the carboxyl terminus, making it a compact, protected building block for peptide and peptidomimetic assembly. The side chain retains the hydroxymethyl functionality characteristic of serine, which supports downstream derivatization or incorporation into structured sequences where a protected amino acid segment is required. This form is commonly selected in synthetic workflows that prioritize controlled coupling of a D-amino acid residue and compatibility with standard protected-amino-acid handling.
1. D-Serine Peptide Building Block
Boc-D-Serine methyl ester is used by peptide chemistry groups to introduce a D-serine residue as a defined stereochemical element within peptide segments or libraries. The Boc-protected amino group supports routine peptide coupling workflows, while the methyl ester provides a protected carboxyl handle that can be carried through stepwise assembly before conversion to the corresponding activated acid or other downstream forms. Researchers developing D-amino-acid-containing peptides for stability studies, conformational control, or structure-activity relationship work often prefer this methyl ester format because it streamlines segment handling and minimizes premature hydrolysis during synthesis and purification.
2. Solid-Phase Peptide Synthesis Segments
Boc-D-Serine methyl ester is frequently incorporated into protected amino acid segment strategies for solid-phase peptide synthesis planning, particularly when a D-serine unit must be positioned with consistent stereochemistry and orthogonal functional-group management. Peptide synthesis service providers and academic peptide cores use this type of protected amino acid derivative to prepare repeatable building blocks for custom peptide manufacturing, where the Boc-protected nitrogen and esterified carboxyl group help maintain integrity across coupling and purification steps. The serine side-chain hydroxyl remains available for later functionalization or for generating serine-derived variants after the peptide backbone is assembled.
3. Peptidomimetic and SAR Intermediates
Boc-D-Serine methyl ester serves as a practical intermediate for peptidomimetic and SAR-focused medicinal chemistry programs that require D-serine-derived fragments. In workflows that convert serine into modified motifs (for example, to tune hydrogen-bonding patterns, steric presentation, or side-chain chemistry), the protected amino/ester functionality supports controlled downstream transformations while preserving the D-configuration. Medicinal chemists and process development teams often select this derivative when they need a stable, isolable intermediate that can be carried from early analog generation into later-stage coupling, side-chain modification, or final scaffold assembly.
4. Side-Chain Hydroxyl Functionalization
Boc-D-Serine methyl ester is also used when the serine side-chain hydroxyl is a key site for subsequent derivatization, such as installing protecting groups or generating side-chain substituted analogs. Chemical biology and materials researchers may start from this derivative to prepare D-serine-containing linkers or peptide conjugation precursors where the side-chain hydroxymethyl group is the functional pivot for attaching additional moieties. Because the amino group and carboxyl terminus are already protected, the hydroxyl can be targeted in a more controlled manner during the preparation of modified peptide building blocks, conjugation-ready fragments, or stereochemically defined serine-containing materials precursors.
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