Boc-Dap(Alloc)-OH is a protected amino acid derivative of diaminopropionic acid (Dap) bearing both an N-terminal Boc (tert-butoxycarbonyl) protecting group and an Alloc (allyloxycarbonyl) protecting group on the side-chain amino functionality. The molecule contains a free carboxyl group and a stereochemically unspecified amino acid backbone, with the remaining amine(s) masked by carbonyl-linked protecting groups that modulate chemoselectivity during synthesis. In peptide chemistry, this orthogonally protected Dap building block is used to support stepwise assembly of peptides or peptidomimetics where controlled deprotection and subsequent functionalization of the side-chain amine are required for crosslinking, conjugation, or structure-activity studies.
CAT No: CP05810
CAS No:161561-83-7
Synonyms/Alias:N-α-Boc-N-β-allyloxycarbonyl-L-2,3-diaminopropionic acid;
Boc-Dap(Alloc)-OH is a protected, chiral amino acid derivative featuring a tert-butoxycarbonyl (Boc) carbamate on the α-amino group and an allyloxycarbonyl (Alloc) protecting group on the side-chain amino functionality of L-2,3-diaminopropanoic acid (Dap). The molecule retains a free carboxylic acid (-CO2H) for C-terminal activation and peptide coupling, while the Boc and Alloc groups provide orthogonal protection that can be selectively removed under compatible conditions. The presence of two nitrogen sites with distinct protecting-group lability enables controlled stepwise derivatization, including side-chain functionalization and sequential deprotection strategies for peptide building block preparation. The stereochemical definition at the α-carbon supports stereocontrolled incorporation into peptide sequences and downstream synthesis of diamino-acid containing analogs used in biochemical research and process-oriented fine chemical workflows.
1. Orthogonal Peptide Building Blocks
Boc-Dap(Alloc)-OH supports orthogonally protected amino acid synthesis for peptide coupling workflows where sequential deprotection is required to expose either the α-amino functionality (Boc removal) or the side-chain amino functionality (Alloc removal). The free carboxylic acid enables standard C-terminal activation to form amide bonds, while the Boc and Alloc groups modulate nucleophilicity and chemoselectivity during chain assembly. The diamino side chain can be preserved as a protected handle during early coupling steps, then revealed for late-stage functionalization or for incorporation into branching or crosslinking motifs. Diaminopropanoic acid incorporation is particularly relevant for generating peptide scaffolds that require controlled presentation of two amine sites for subsequent conjugation chemistry and structure-function studies.
2. Side-Chain Functionalization Chemistry
Boc-Dap(Alloc)-OH is suitable for side-chain functionalization strategies that exploit the Alloc-protected amino group as a protected nucleophile for subsequent derivatization after selective deprotection. The orthogonal protecting-group scheme allows conversion of the exposed side-chain amine into urea, sulfonamide, carbamate, or amide derivatives, enabling preparation of amino acid modified intermediates for peptidomimetic construction and molecular recognition probes. The retained carboxylic acid supports additional derivatization routes, including formation of activated esters or coupling partners used to extend functional groups onto a peptide or polymer backbone. The resulting functionalized diamino-acid derivatives can be used to tune charge density and hydrogen-bonding patterns that influence binding behavior in chemical biology and SAR-oriented molecular design.
3. Chemical Biology And Bioconjugation
Boc-Dap(Alloc)-OH can be applied to chemical biology workflows that require controlled introduction of a diamino-acid motif into peptide-based probes and labeling reagents. The dual protected amine pattern supports stepwise preparation of conjugation-ready intermediates, where selective unmasking of the side-chain amine enables attachment of electrophiles, tags, or affinity handles while maintaining compatibility with peptide-grade coupling chemistry. The free carboxylic acid facilitates incorporation into peptide fragments that can later undergo conjugation to biomolecules through amide formation or subsequent functional group transformations. Diamino-acid containing constructs can serve as building blocks for studying molecular interactions, mapping binding interfaces, and generating defined probe architectures for downstream analytical characterization.
4. Process Chemistry Intermediate Preparation
Boc-Dap(Alloc)-OH is relevant to process chemistry intermediate preparation for manufacturing routes that require orthogonally protected amino acid derivatives with predictable deprotection selectivity and controlled handling of reactive amine groups. The Boc and Alloc protecting groups provide a practical strategy to suppress undesired side reactions during isolation, storage, and sequential synthetic steps, while the carboxylic acid allows conversion to activated forms for downstream coupling operations. The defined stereocenter at the α-carbon supports stereochemically consistent incorporation into peptide building blocks, which can be advantageous for reproducible intermediate quality in fine chemical synthesis. The compound's protected diamino functionality aligns with industrially scalable approaches to protected amino acid synthesis, enabling stepwise production of complex peptide intermediates used in specialty chemical production and peptide-manufacturing pipelines.
5. Peptidomimetics And SAR Studies
Boc-Dap(Alloc)-OH is suitable for peptidomimetic construction and structure-activity relationship studies where diamino-acid residues are used to modulate conformational preferences, electrostatic interactions, and hydrogen-bonding networks. The orthogonally protected amines enable controlled incorporation into peptide analogs, followed by selective unmasking to introduce side-chain substituents that can tune potency-relevant physicochemical properties without altering the core stereochemistry. The free carboxylic acid supports iterative assembly of analog libraries through peptide coupling chemistry, while the protected side-chain provides a handle for late-stage diversification. The resulting diamino-acid containing analogs can be employed as defined chemical entities in medicinal chemistry research programs and SAR-driven optimization campaigns focused on molecular recognition and binding-site mapping.
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