Boc-Imidazole-COOH is a Boc-protected imidazole-containing amino acid derivative featuring an imidazole side chain and a carboxylic acid group, making it a non-proteinogenic building block for peptide chemistry. The molecule bears a tert-butoxycarbonyl (Boc) protecting group on the amino functionality, which suppresses uncontrolled amide formation during coupling while leaving the carboxyl group available for further transformations or incorporation into peptide intermediates. In synthesis workflows, it is employed as a protected amino acid precursor to introduce an imidazole-bearing residue into peptides or peptide-related structures for studies of side-chain polarity, metal-binding motifs, or structure-activity relationships.
CAT No: CP26288
CAS No:128293-64-1
Synonyms/Alias:4-(Boc-amino)-1-methyl-1H-imidazole-2-carboxylic acid;128293-64-1;4-((tert-Butoxycarbonyl)amino)-1-methyl-1H-imidazole-2-carboxylicacid;4-tert-butoxycarbonylamino-1-methyl-1h-imidazole-2-carboxylicacid;4-[(tert-butoxycarbonyl)amino]-1-methylimidazole-2-carboxylicacid;4-(boc-amino)-1-methylimidazole-2-carboxylicacid;4-(boc-amino)-1-methyl-1h-imidazole-2-carboxylicacid;4-(tert-butoxycarbonylamino)-1-methyl-1H-imidazole-2-carboxylicacid;1H-Imidazole-2-carboxylicacid,4-[[(1,1-dimethylethoxy)carbonyl]amino]-1-methyl-;4-[(tert-butoxycarbonyl)amino]-1-methyl-1h-imidazole-2-carboxylicacid;AC1MBVDM;PubChem23762;ACMC-1CAXK;boc-nh(4)-meimd-(2)-oh;SCHEMBL1986577;CTK0H3701;GZBSJWBQXNCOFP-UHFFFAOYSA-N;MolPort-000-152-505;ZINC2506603;5410AA;AN-433;ANW-64020;1-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]imidazole-2-carboxylicAcid;AKOS015902105;AB13245;AJ-36125
Boc-Imidazole-COOH is a Boc-protected imidazole-containing amino acid building block featuring a carboxylic acid functionality for downstream coupling and peptide assembly. The imidazole side chain provides a chemically distinctive aromatic heterocycle commonly leveraged in histidine-mimetic design, while the Boc group supports controlled reactivity during synthesis and intermediate preparation. This reagent is frequently used by peptide chemistry and medicinal chemistry teams to introduce an imidazole-bearing residue or to prepare defined imidazole-containing fragments for structure-activity relationship studies.
1. Peptide Building Blocks
Boc-Imidazole-COOH is used as an imidazole-containing protected amino acid building block for custom peptide synthesis workflows where a Boc-protected amino component is required for controlled coupling and fragment assembly. Peptide synthesis groups rely on the carboxylic acid handle for incorporation into peptide chains and on the imidazole side chain to reproduce histidine-like chemical features in short peptides, peptide libraries, and SAR-focused analog series. The protected format helps maintain compatibility with stepwise synthesis and purification strategies used in research-grade peptide manufacturing.
2. Medicinal Chemistry Intermediates
Boc-Imidazole-COOH serves as a practical intermediate for medicinal chemistry programs that need defined imidazole-bearing motifs for small-molecule or peptidomimetic scaffolds. Medicinal chemistry and process development teams commonly incorporate imidazole functionality to tune physicochemical properties and enable heteroaromatic interactions in lead optimization campaigns, while the Boc protection provides a convenient protected amine form during fragment elaboration. The reagent's combination of protected amino functionality and a free carboxylic acid supports modular downstream conversion into coupling-ready derivatives and structured intermediate sets.
3. Imidazole-Functional Fragment Synthesis
Boc-Imidazole-COOH is applied in the preparation of imidazole-containing fragments used for conjugation chemistry and chemical biology reagent development, where a stable, protected amino acid precursor simplifies controlled assembly of defined heteroaromatic building units. Researchers preparing labeled or functionalized imidazole motifs for binding studies, linker construction, or scaffold diversification benefit from the imidazole side chain as a chemically recognizable handle and from the Boc-protected amino group as a synthesis-compatible protection strategy. This makes the compound useful for workflows that require reproducible intermediate quality and clear functional-group differentiation for subsequent derivatization steps.
4. Analytical Reference Material Prep
Boc-Imidazole-COOH is also used to prepare defined standards and analytical reference samples for method development in peptide and small-molecule analysis. Analytical chemistry teams preparing LC-MS or related characterization workflows may use the reagent to generate calibration or qualification materials containing an imidazole-bearing protected amino acid motif. The defined functional-group pattern helps ensure consistent retention and fragmentation behavior across runs when developing assays for intermediate mixtures, peptide fragments, or reaction monitoring samples.
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