Boc-Dab(Aloc)-OH is a protected amino acid derivative featuring the Dab (2,4-diaminobutyric acid) backbone bearing both an N-terminal Boc (tert-butoxycarbonyl) group and an Alloc (allyloxycarbonyl) protecting group on the side-chain amino functionality. The molecule contains the free carboxylic acid group alongside protected amines, with the Boc and Alloc groups serving to control chemoselectivity by suppressing undesired amide/urea formation during stepwise peptide coupling and allowing orthogonal deprotection strategies when required. In peptide chemistry, it is used as a building block to introduce a diamino acid residue with orthogonally protected nitrogens for the synthesis of peptides and amino acid derivatives used in structure-function studies and chemical biology workflows.
CAT No: CP26506
CAS No:171820-73-8
Synonyms/Alias:Boc-Dab(Aloc)-OH;171820-73-8;Nalpha-Boc-Ngamma-allyloxycarbonyl-L-2,4-diaminobutyricacid;AmbotzBAA1085;AC1ODUMA;CTK8E6916;ZINC2569772;6304AH;AKOS015901094;AJ-41765;RT-014651;A-8370;I14-15347;Na-Boc-Ng-allyloxycarbonyl-L-2,4-diaminobutyricacid;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-(prop-2-enoxycarbonylamino)butanoicacid
Boc-Dab(Aloc)-OH is a protected amino acid derivative built on Dab (2,4-diaminobutyric acid) with an N-terminal Boc protecting group and an Aloc (allyloxycarbonyl) protecting group on the side-chain amino functionality. This orthogonally protected diamino building block is designed for controlled, stepwise deprotection during peptide assembly, enabling selective functionalization of the diamine side chain in complex peptide and peptidomimetic syntheses. The presence of both Boc and Aloc groups supports downstream workflows where chemoselective exposure of the reactive amines is required for coupling, cyclization, or attachment of additional moieties.
1. Orthogonal Peptide Building Block
Boc-Dab(Aloc)-OH is used as a protected diamino amino acid building block for constructing peptides and peptidomimetics where selective side-chain amine handling is essential. Peptide synthesis teams rely on the Boc/Aloc protection pattern to manage the two amino functionalities on Dab, allowing the synthesis to proceed without premature side-chain reactivity and then to reveal the Aloc-protected amine at a chosen stage for subsequent coupling steps. This is particularly valuable for sequences that require controlled introduction of additional substituents on the Dab side chain, such as further amide formation or incorporation into constrained motifs.
2. Site-Selective Side-Chain Functionalization
Boc-Dab(Aloc)-OH supports workflows that need site-selective modification of the Dab side chain after peptide chain assembly. In chemical biology and peptide engineering settings, researchers often use orthogonally protected amino acids to generate a peptide intermediate bearing a selectively unmasked amine, which can then be used for attachment of functional groups such as additional linkers, solubilizing handles, or conjugation-ready moieties. The protected diamine nature of this building block helps maintain compatibility with peptide coupling conditions while preserving the ability to perform downstream derivatization on the Dab residue in a controlled manner.
3. Peptide Cyclization And Constrained Motifs
Boc-Dab(Aloc)-OH is frequently selected when the target peptide architecture benefits from controlled diamine availability for cyclization strategies. After peptide assembly, selective exposure of the Aloc-protected amine enables intramolecular or intermolecular bond formation routes that generate constrained structures, including ring-containing peptidomimetics and stapled or bridged analogs that incorporate Dab-derived linkages. This makes the building block useful for medicinal chemistry teams developing conformationally restricted peptide scaffolds where precise placement of reactive amines at the Dab position drives the formation of the desired constrained motif.
4. Pharmaceutical Intermediate Development
Boc-Dab(Aloc)-OH is also used in the preparation of advanced peptide-related intermediates for pharmaceutical intermediate development and custom peptide manufacturing research. Process chemists and peptide development groups value the orthogonal protection strategy because it supports staged transformations: the protected amino acid can be incorporated into a growing peptide framework, and the selectively unmasked amine can be carried forward into the next synthetic step without uncontrolled side reactions from the diamine functionality. This approach is commonly applied when building blocks must be processed through multiple coupling and derivatization stages while maintaining chemoselectivity over the Dab side-chain reactivity.
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