Boc-D-Asp(OFm)-OH is a protected amino acid derivative of D-aspartic acid featuring an N-terminal Boc (tert-butoxycarbonyl) carbamate and a side-chain esterified aspartate oxygen bearing an OFm group. The molecule contains both an amino functionality masked as a Boc-protected carbamate and a carboxylic acid at the α-position, while the side-chain carboxyl is converted to an OFm-protected form that modulates chemoselectivity during peptide assembly. In peptide synthesis workflows, this orthogonally protected aspartate analogue is employed as a stepwise building block to control side-chain reactivity and to enable incorporation of a D-configured aspartyl residue into larger peptide structures for structure-activity and labeling studies.
CAT No: CP26259
CAS No:123417-19-6
Synonyms/Alias:Boc-D-Asp(Ofm)-OH;123417-19-6;ZINC2517110;6314AH;AM002392;I14-32676;(2R)-2-[(TERT-BUTOXYCARBONYL)AMINO]-4-(9H-FLUOREN-9-YLMETHOXY)-4-OXOBUTANOICACID
Boc-D-Asp(OFm)-OH is a protected D-configured aspartic acid derivative designed for peptide synthesis and as a stereochemically defined building block. The backbone amino group is protected as a Boc carbamate, while the side-chain carboxyl group is masked as an OFm (Fm) ester, providing controlled chemoselectivity during segment coupling and subsequent functionalization steps. This protected format is commonly selected when maintaining D-stereochemistry at the aspartate position and deferring side-chain reactivity until later stages of assembly.
1. D-Asp Residue Incorporation
Boc-D-Asp(OFm)-OH is used by peptide chemists to introduce a stereochemically defined D-aspartate residue into peptide sequences where inversion of configuration or conformational effects are required. Solid-phase and solution-phase peptide workflows benefit from the protected amino and side-chain carboxyl groups, which help prevent premature side reactions during chain elongation. Researchers developing D-amino acid-containing peptides for structure-function studies, protease-stability investigations, or conformational control frequently choose this specific protection pattern to preserve the D stereocenter through assembly and to enable later side-chain activation or derivatization.
2. Orthogonally Managed Side-Chain Chemistry
Boc-D-Asp(OFm)-OH supports downstream strategies that require selective handling of the aspartate side chain after peptide assembly. The OFm ester protection on the side-chain carboxyl allows chemists to manage when the side-chain becomes available for coupling, salt formation, or conversion into activated derivatives for further functionalization. This makes the reagent useful in workflows where the peptide must be completed under conditions that are compatible with the Boc-protected amino group, followed by controlled side-chain processing to generate aspartate-functional peptide variants for SAR studies, binding assays, or material-binding motif optimization.
3. Pharmaceutical Peptide Intermediate Development
Boc-D-Asp(OFm)-OH is frequently employed in the preparation of protected peptide intermediates used in medicinal chemistry programs, particularly when D-aspartate residues are incorporated into peptidomimetic scaffolds or peptide-like candidates. The reagent's protected, stereodefined nature supports reproducible intermediate manufacture, enabling consistent composition of key segments for custom peptide synthesis and scale-up of fragment coupling. Development teams use this building block to assemble D-aspartate-containing sequences that can later be converted into final lead structures or used as reference materials during iterative analogue design, where maintaining stereochemical integrity is critical for structure-activity relationship work.
4. Analytical Reference for Protected Peptides
Boc-D-Asp(OFm)-OH is also used to prepare defined protected peptide standards and intermediate reference materials for method development and characterization by LC-MS and related analytical workflows. Because it is a single, stereochemically defined, protected aspartate building block, it can serve as a starting point for generating consistent peptide fragments or model compounds used to verify identity, monitor coupling efficiency, and support troubleshooting in peptide synthesis. Analytical chemistry teams and peptide manufacturing groups value such standards when comparing reaction outcomes across batches or when validating analytical methods for D-amino acid-containing peptide intermediates.
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