Boc2-3,5-DABA-OH is a Boc-protected amino acid derivative featuring a substituted aromatic side chain derived from 3,5-diaminobenzoic acid, with the molecule bearing amino acid functionality suitable for peptide-related synthesis. The structure contains a carboxylic acid group and two Boc-protected amino substituents on the aromatic ring, which masks the primary amines to control chemoselectivity and suppress undesired side reactions during stepwise coupling chemistry. In research workflows, this protected derivative is used as a precursor for constructing modified aromatic amino acid residues in peptide analogues, as well as for preparing benzoic-acid-based conjugates and labeled or functionalized aromatic building blocks through subsequent deprotection and derivatization steps.
CAT No: CP25320
CAS No:133887-83-9
Synonyms/Alias:133887-83-9;3,5-Bis((tert-butoxycarbonyl)amino)benzoicacid;3,5-Bis-Boc-aminobenzoicacid;3,5-bis[(tert-butoxycarbonyl)amino]benzoicacid;AmbotzBAA1324;AC1LT3LU;SCHEMBL6232755;CTK4B8848;MolPort-000-001-412;SSZRVVHPLPWQCW-UHFFFAOYSA-N;3,5-bis[(2-methylpropan-2-yl)oxycarbonylamino]benzoicAcid;ZINC1420481;6137AA;ANW-55746;AKOS016001135;RTR-004592;AJ-25750;AK-58163;AM014921;OR069587;BIS-N-BOC-3,5-DIAMINOBENZOICACID;KB-234081;ST2404608;4CH-003558;3,5-di-(tert-butoxycarbonylamino)benzoicacid
Chemical Name:Bis-t-Butyloxycarbonyl-3,5-diaminobenzoic acid
Boc2-3,5-DABA-OH is a Boc-protected, substituted amino acid building block featuring a 3,5-dialkyl substituted aromatic side chain (DABA motif) and a carboxylic acid handle, designed for incorporation into peptide-like structures and medicinal chemistry intermediates. The presence of the Boc protecting group makes it a protected amino component commonly handled under standard peptide synthesis conditions, while the aromatic side chain supports downstream derivatization and structure-driven SAR workflows. Researchers typically select this reagent when they need a defined, protected aromatic amino acid unit for assembling complex amide-containing scaffolds.
1. Peptide Building Block Use
Boc2-3,5-DABA-OH is used as a protected amino acid building block for custom peptide synthesis and peptide-mimetic assembly where an aromatic DABA-containing residue is required. Medicinal chemistry groups and peptide manufacturing teams rely on such Boc-protected components to control chemoselectivity during segment coupling and to ensure consistent incorporation of the substituted aromatic side chain into the growing chain. The free carboxylic acid functionality supports conversion to activated derivatives as part of standard peptide assembly workflows, enabling the preparation of research-grade sequences used for structure-activity relationship (SAR) studies and binding-site mapping with defined residue composition.
2. Pharmaceutical Intermediate Synthesis
Boc2-3,5-DABA-OH serves as a practical intermediate for preparing aromatic amide-rich scaffolds in small-molecule and peptidomimetic discovery programs. In pharmaceutical intermediate development, the defined substituted aromatic side chain and protected amino functionality help route synthesis toward analog series where the 3,5-DABA motif is a structural element. Process development and synthetic chemistry teams often choose this type of protected building block to streamline downstream transformations that require a controlled amine protection state and a carboxylic acid group for further functionalization into coupling-ready intermediates.
3. SAR Analog Library Construction
Boc2-3,5-DABA-OH is well suited for generating residue-defined analog libraries in medicinal chemistry, particularly when aromatic substitution patterns at the 3,5-positions must be maintained across a series. Chemical biology and drug discovery groups use this reagent to build consistent "core" fragments that can be varied at other positions while keeping the DABA-containing aromatic unit constant, improving interpretability of structure-activity trends. The protected amino acid form supports parallel synthesis workflows where multiple analogs are assembled and compared under the same coupling logic, helping teams efficiently evaluate how the aromatic side-chain environment influences scaffold performance in downstream assays.
4. Amide-Linked Scaffold Derivatization
Boc2-3,5-DABA-OH is frequently used to construct amide-linked scaffolds by providing both a protected amine and a carboxylic acid functionality for controlled coupling chemistry. Specialty synthesis groups and materials-oriented medicinal chemistry labs incorporate such protected aromatic amino acid units into linkers and backbone segments that later undergo further derivatization, such as conversion into coupling partners for attaching additional functional groups. This makes the reagent useful when a defined aromatic residue must be presented within a larger chemical framework while maintaining compatibility with standard organic synthesis steps used to assemble complex, research-grade conjugates and analogs.
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