Boc-Dap(Z)-OH is an Nα-Boc-protected amino acid derivative of 2,3-diaminopropanoic acid (diaminopropionic acid) bearing a Z-protected side-chain amino functionality, placing it within the protected amino acid class used for peptide building blocks. The molecule contains a Boc carbamate that masks the α-amino group while the side-chain is protected as a Z-type amino protecting group, and it also presents a free carboxylic acid for controlled coupling chemistry. In peptide synthesis workflows, the orthogonal protection pattern supports stepwise assembly by reducing undesired side reactions from unprotected amines and providing a defined functional handle for amide bond formation to generate protected peptide intermediates.
CAT No: CP27334
CAS No:65710-57-8
Synonyms/Alias:65710-57-8;Boc-Dap(Cbz)-OH;Boc-N3-Cbz-L-2,3-diaminopropionicacid;(S)-3-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)propanoicacid;(S)-2-(N-BOC-AMINO)-3-(N-CBZ-AMINO)PROPIONICACID;(S)-2-[(tert-Butoxycarbonyl)amino]-3-(benzyloxycarbonylamino)propionicacid;AC1MBSGG;SCHEMBL1022494;MolPort-008-267-382;QKMSMVGTLTVHLK-LBPRGKRZSA-N;ACT04322;ZINC2560695;ABP000778;AN-917;SBB067073;Nalpha-Boc-Nbeta-Cbz-amino-L-alanine;AKOS005146393;AKOS007930331;AC-5656;CB-3106;EBD2208197;Nalpha,Nbeta-(S)-diaminopropionicacid;AJ-40627;AK-43434;BR-43434
Boc-Dap(Z)-OH is a protected, stereodefined amino acid building block used in peptide and peptidomimetic synthesis, featuring a Boc-protected alpha-amino group and a side-chain protected diaminopropyl motif. The Z-protecting group on the side-chain is designed to control chemoselectivity during sequential coupling and deprotection steps, enabling access to protected lysine-like or diamine-containing peptide segments. This reagent is commonly selected by peptide chemistry groups that require robust side-chain protection compatible with standard protected-amino-acid workflows and downstream intermediate handling.
1. Fmoc-Free Peptide Synthesis
Boc-Dap(Z)-OH is frequently used as a protected amino acid residue for assembling peptides in synthetic workflows that rely on Boc-based protection strategies rather than Fmoc chemistry. Peptide synthesis groups use this building block to introduce a diamine-bearing side chain with controlled reactivity, supporting the preparation of peptide sequences where orthogonal side-chain management is critical to avoid premature side-chain cross-reactions. In custom peptide manufacturing and academic peptide chemistry, the Boc/Z protection pattern helps maintain the integrity of the side-chain functionality through iterative coupling and purification, while still allowing planned deprotection to reveal the functional diamine for subsequent transformations or final peptide generation.
2. Diamine-Containing Segment Building
Boc-Dap(Z)-OH is well suited for constructing peptide segments that require a protected diamine functionality for later derivatization, such as in peptide-based linkers, cationic peptide motifs, or structure-function studies where side-chain charge and spacing are important. Researchers in chemical biology and medicinal chemistry often incorporate protected diamine residues to tune local electrostatics and enable controlled post-assembly modification without interfering with backbone coupling. The Z-protected side chain provides a practical handle for maintaining chemoselectivity during segment condensation and for delivering a defined protected intermediate that can be carried forward into larger assemblies or used to generate targeted peptide variants.
3. Pharmaceutical Intermediate Development
Boc-Dap(Z)-OH is used as a pharmaceutical-intermediate building block for preparing protected diamine-containing intermediates that can feed into larger synthetic programs, including the generation of peptide-like scaffolds and amine-functionalized intermediates for medicinal chemistry. Process development teams value this reagent because its protection strategy supports stepwise synthesis planning, allowing the diamine functionality to remain masked until the appropriate stage of the route. In industrial and translational chemistry settings, Boc-Dap(Z)-OH is therefore selected when a stable, isolable protected amino acid unit is required to control reactivity and maintain reproducibility across multi-step intermediate synthesis.
4. Side-Chain Derivatization Precursors
Boc-Dap(Z)-OH is commonly positioned as a precursor for downstream side-chain functionalization workflows where the diamine group must be liberated or transformed after peptide assembly. Chemical biology users and materials researchers often prepare protected diamine-containing peptides or peptide fragments first, then perform later-stage modifications such as conversion to alternative protected forms, coupling to electrophiles, or incorporation into functional conjugates that require controlled amine chemistry. The Boc/Z protection pattern supports a workflow in which the backbone remains protected and the side-chain reactivity is managed until the desired derivatization step, improving compatibility with purification and analytical characterization of intermediate and final products.
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