Boc-Asp-NH2 is a protected amino acid derivative consisting of L-aspartic acid (Asp) in which the α-amino group is protected with a tert-butoxycarbonyl (Boc) carbamate and the carboxyl group is converted to a primary amide (-CONH2), forming an Asp-NH2 amide. The side chain contains a β-carboxamide functionality that provides an additional polar hydrogen-bonding motif distinct from the free carboxylic acid form, while the Boc group controls chemoselectivity by masking the α-amine during stepwise coupling chemistry. Boc-Asp-NH2 is used in peptide and amide synthesis as a protected building block that allows incorporation of the aspartamide side-chain pattern into larger peptide-related intermediates and enables preparation of aspartyl-containing analogues for structure-activity, labeling, or analytical method development.
CAT No: CP27423
CAS No:74244-17-0
Synonyms/Alias:Boc-Asp-NH2;74244-17-0;Boc-L-asparticacid1-amide;Boc-L-isoasparagine;AC1Q1MRQ;15037_ALDRICH;SCHEMBL2130020;SCHEMBL9219658;15037_FLUKA;CTK8F8265;MolPort-003-926-617;ZINC2555021;Boc-Isoasn-OH,Boc-L-isoasparagine;KM1601;AKOS016004416;AJ-39671;AK-89809;AN-37188;BP-12800;KB-48253;FT-0686525;V7573;(3S)-4-amino-3-(tert-butoxycarbonylamino)-4-oxo-butanoicacid;(S)-4-Amino-3-((tert-butoxycarbonyl)amino)-4-oxobutanoicacid
Boc-Asp-NH2 is an amino acid amide derivative featuring the Asp side chain and an N-terminal Boc protecting group, providing a protected, condensation-ready building block for peptide and peptidomimetic synthesis workflows. The side-chain carboxamide functionality is positioned to support controlled coupling during segment assembly, while the Boc group enables compatibility with standard protected-amino-acid handling in solution-phase or automated peptide manufacturing contexts. This reagent is typically selected when a terminal amide motif derived from aspartic acid is required and when a protected amino functionality is advantageous for downstream transformations.
1. Terminal Aspartamide Building
Boc-Asp-NH2 is used by peptide and peptidomimetic development groups to construct C-terminal aspartamide motifs, where the amide terminus is introduced from the outset as a defined synthetic handle. Custom peptide synthesis teams often choose this Boc-protected amino acid amide to ensure the terminal functionality remains protected during earlier coupling steps, improving overall sequence fidelity for short to mid-length peptides. Pharmaceutical intermediate development groups also rely on this format to prepare aspartamide-containing fragments that can be incorporated into larger bioactive or screening libraries.
2. Protected Coupling Segment
Boc-Asp-NH2 serves as a protected coupling segment for assembling Asp-containing peptide fragments in automated or manual workflows, particularly when the downstream sequence requires consistent protection of the amino functionality during condensation. Peptide manufacturing researchers commonly incorporate this reagent into stepwise segment assembly strategies to reduce variability from handling free amino acids and to streamline purification workflows associated with incomplete coupling at terminal positions. The Boc-protection pattern supports controlled deprotection and subsequent activation steps within established peptide synthesis protocols, making it a practical choice for building defined intermediates for later purification and final assembly.
3. Peptidomimetic Intermediate Synthesis
Boc-Asp-NH2 is frequently applied in medicinal chemistry programs that generate peptidomimetic scaffolds incorporating aspartamide-like linkages, where precise functional group placement is essential for structure-activity relationship studies. Chemical biology and small-molecule discovery teams use this building block to prepare aspartamide-containing intermediates that can be diversified through subsequent coupling or functional group transformations while maintaining the protected amino acid framework through early development stages. This reagent's protected, amide-bearing design helps support reproducible synthesis of analog series used in screening and assay development workflows.
4. Library-Scale Fragment Assembly
Boc-Asp-NH2 is well suited for parallel synthesis and library-scale fragment assembly in which Asp-derived amide termini must be introduced consistently across many analogs. Research groups performing peptide library construction or focused SAR campaigns often select this protected amino acid amide to standardize the terminal functional group and reduce the risk of side reactions associated with unprotected termini during repeated coupling cycles. By providing a defined Boc-protected amino acid amide input, it supports efficient generation of Asp-containing fragment sets that can be carried forward into final peptide assembly or further medicinal chemistry elaboration.
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