Boc-L-Dap-OH is the Boc-protected form of L-2,3-diaminopropanoic acid (L-Dap), an amino acid derivative featuring a primary amino-bearing side chain characteristic of the diamino acid class. The molecule contains a free carboxylic acid and an N-terminal tert-butoxycarbonyl (Boc) protecting group that masks one amino functionality to control chemoselectivity during coupling, while the remaining side-chain primary amine provides a reactive handle for further derivatization. Boc-L-Dap-OH is used as a protected amino acid building block in peptide synthesis workflows, including stepwise assembly where orthogonal functional-group management and selective reaction at the carboxyl-activated position are required for constructing peptide and amino-acid conjugate targets.
CAT No: CP26018
CAS No:73259-81-1
Synonyms/Alias:Boc-Dap-OH;73259-81-1;Boc-L-2,3-diaminopropionicacid;(S)-3-Amino-2-((tert-butoxycarbonyl)amino)propanoicacid;3-Amino-Boc-L-alanine;Boc-Dpr-OH;3-Amino-N-Boc-L-alanine;3-Amino-(tert-butoxycarbonyl)-L-alanine;(N-Boc-beta-amino)-Ala-OH;(S)-3-Amino-2-(tert-butoxycarbonylamino)propanoicacid;N-Boc-L-2,3-diaminopropanoicacid;MFCD00236843;SBB065814;Nalpha-Boc-2,3-diaminopropionicAcid;(S)-3-Amino-2-(tert-butoxycarbonylamino)propionicAcid;N-ALPHA-L-(BUTOXYCARBONYL)-2,3-DIAMINOPROPIONICACID;Nalpha-Boc-L-2,3-diaminopropionicacid;(2S)-3-amino-2-{[(tert-butoxy)carbonyl]amino}propanoicacid;(2S)-3-AMINO-2-([(TERT-BUTOXY)CARBONYL]AMINO)PROPANOICACID;PubChem13819;BOC-DAPA-OH;BOC-L-DAPA-OH;AC1MBSG4;AC1Q1MSN;BOC-L-DAP-OH
Chemical Name:N-alpha-t-Butyloxycarbonyl-L-2,3-diaminopropionic acid
Boc-L-Dap-OH is a Boc-protected amino acid building block derived from L-2,3-diaminopropanoic acid (Dap), featuring a carbamate-protected alpha-amino group alongside a free side-chain primary amine. This protected diamino functionality makes it a practical reagent for constructing peptides and peptidomimetic scaffolds where controlled amine reactivity is required during assembly. The Boc group supports standard peptide synthesis workflows, while the unprotected side-chain amine provides a handle for downstream functionalization and selective coupling steps.
1. Peptide Synthesis Building Block
Boc-L-Dap-OH is used by peptide synthesis groups to incorporate the Dap residue into protected peptide segments where side-chain amine chemistry must be managed carefully. The Boc-protected alpha-amino functionality enables controlled condensation strategies during custom peptide manufacturing and research-grade peptide library construction, while the free side-chain primary amine supports subsequent derivatization after peptide assembly. This makes the reagent particularly relevant for sequences that require diamino side-chain presentation for charge tuning, hydrogen-bonding patterns, or attachment of further substituents in later steps.
2. Peptidomimetic Side-Chain Functionalization
Boc-L-Dap-OH is frequently selected for medicinal chemistry and chemical biology programs that need a stable, protected diamino intermediate to generate peptidomimetic analogs with tailored side-chain properties. The combination of a Boc-protected backbone position with an available primary amine allows developers to introduce amide, urea, or other nitrogen-containing substituents in downstream modification workflows, supporting structure-activity relationship studies that rely on systematic side-chain variation. Researchers also use this building block to prepare libraries of Dap-containing analogs where controlled functional group placement is essential for reproducible coupling and purification.
3. Pharmaceutical Intermediate Development
Boc-L-Dap-OH serves as a practical pharmaceutical intermediate for manufacturing teams and process chemists preparing nitrogen-rich intermediates for further synthetic elaboration. The Boc protection helps maintain the alpha-amino group under conditions used for side-chain chemistry, enabling stepwise conversion of the free primary amine into downstream derivatives used in route development. This reagent is therefore commonly used in the preparation of amine-functional intermediates that feed into broader small-molecule and peptidomimetic synthesis campaigns, including scale-up-oriented workflows where protecting-group stability and predictable reactivity are important.
4. Chemical Biology Conjugation Handles
Boc-L-Dap-OH is applied in chemical biology workflows that require an amino-functional handle for attaching Dap-containing motifs to larger scaffolds. The free primary side-chain amine supports coupling chemistries used to generate conjugates such as amide-linked constructs, affinity reagents, or labeled peptide derivatives used in target-binding and interaction studies. Because the alpha-amino group is protected, the building block can be incorporated into defined peptide fragments before conjugation, helping researchers maintain site control during the transition from a synthesized peptide intermediate to a functionalized probe or conjugate.
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