Boc-Dap-OtBu is a protected amino acid derivative of 2,3-diaminopropanoic acid (diaminopropionic acid) featuring an N-terminal Boc (tert-butoxycarbonyl) carbamate and a C-terminal tert-butyl ester (OtBu). The molecule contains the amino acid backbone with two side-chain amino functionalities, while the Boc and OtBu groups mask the corresponding reactive sites to control chemoselectivity and suppress undesired side reactions during stepwise coupling. Boc-Dap-OtBu is used as a protected building block for peptide synthesis and for preparing more complex amino acid and peptide derivatives that require a protected diamino side chain for subsequent functionalization or deprotection.
CAT No: CP27457
CAS No:77215-54-4
Synonyms/Alias:ZINC34456714;AKOS025286348;AK165924;(S)-tert-Butyl3-amino-2-((tert-butoxycarbonyl)amino)propanoate;77215-54-4
Boc-Dap-OtBu is a protected, stereodefined amino acid building block featuring a Boc-protected amino group and an O-tert-butyl ester-protected side-chain carboxylate, providing orthogonal functional-group masking for downstream peptide assembly and intermediate chemistry. This protected diaminopropionic acid derivative is commonly handled as a stable solid/solid-like reagent for controlled coupling steps where side-chain carboxyl functionality must remain masked until the desired stage of synthesis.
1. Solid-Phase Peptide Synthesis
Boc-Dap-OtBu is used by peptide synthesis groups to introduce a protected Dap residue into peptide sequences while maintaining side-chain carboxyl protection during chain elongation. The Boc group supports established peptide-building workflows where the amino functionality is temporarily protected to prevent premature reactions, and the tert-butyl ester helps preserve the side-chain carboxyl group against undesired coupling or activation. Researchers developing peptide libraries, constrained peptide motifs, or stereochemically defined peptide analogs rely on this type of protected amino acid to manage functional-group compatibility across multiple coupling/deprotection cycles.
2. Peptide Segment Coupling
Boc-Dap-OtBu is frequently selected for solution-phase segment condensation and modular peptide assembly where defined protected amino acid residues are incorporated into larger intermediates. In these workflows, the reagent's dual protection pattern (Boc on the α-amino function and tert-butyl ester on the side-chain carboxyl) supports sequential construction of peptide fragments with reduced risk of side reactions from free carboxyl groups. Custom peptide manufacturing and medicinal chemistry teams use this protected building block when they need a reliable handle for later deprotection and functional diversification at the Dap side chain.
3. Protected Amino Acid Intermediate Development
Boc-Dap-OtBu serves as a practical intermediate for preparing further amino acid derivatives and protected Dap-containing building blocks used in downstream synthetic programs. Process and development chemists incorporate this reagent into intermediate sequences where the side-chain carboxyl must remain protected during transformations that would otherwise be incompatible with a free acid. This application is especially relevant for manufacturing workflows that require chemoselective deprotection timing, enabling conversion of the tert-butyl ester to the corresponding carboxylic acid at a controlled stage for subsequent coupling, derivatization, or incorporation into more complex structures.
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