Boc-L-Idc-OH contains the amino acid side chain of L-Idc (imidazole-containing indole-like carbon framework) linked to a carboxylic acid, with the α-amino group protected as a Boc (tert-butoxycarbonyl) carbamate. The molecule therefore bears a free carboxyl functional group alongside a Boc-protected amine, and the stereochemistry is specified as L at the α-carbon. In peptide synthesis workflows, the Boc protection supports chemoselective handling of the amino functionality during stepwise assembly of amino acid derivatives and can serve as a precursor to Boc-deprotected Idc-containing building blocks for incorporation into peptides or peptide-related intermediates.
CAT No: CP25355
CAS No:144069-67-0
Synonyms/Alias:144069-67-0;(S)-1-(tert-Butoxycarbonyl)indoline-2-carboxylicacid;Boc-L-indoline-2-carboxylicacid;Boc-L-Idc-OH;AmbotzBAA1405;AC1MBSGV;SCHEMBL927332;CTK7I3223;MolPort-003-725-654;QONNUMLEACJFME-NSHDSACASA-N;BOC--INDOLINECARBOXYLICACID;ZINC4287377;7088AA;AKOS015911607;RTR-005617;AJ-50233;AK115650;AN-31521;KB-210738;TR-005617;FT-0679894;BOC-(S)-(-)-INDOLINE-2-CARBOXYLICACID;(S)-N-tert-butoxycarbonylindoline-2-carboxylicacid;(2S)-1-tert-butoxycarbonylindoline-2-carboxylicacid;I14-38292
Chemical Name:(S)-N-alpha-t-Butyloxycarbonyl-2-indolinecarboxylic acid
Boc-L-Idc-OH is a Boc-protected L-Idc amino acid building block used in peptide and peptidomimetic synthesis workflows. With a tert-butoxycarbonyl (Boc) group protecting the amino functionality, it is designed to participate as an amino acid residue under controlled coupling conditions while minimizing undesired side reactions. Idc (imidazole-2-carboxylic acid) contributes an imidazole-containing side chain that is commonly leveraged to introduce histidine-like coordination and hydrogen-bonding motifs into synthetic peptides and medicinal chemistry leads.
1. Peptide Building Block
Boc-L-Idc-OH is frequently selected by peptide synthesis groups to incorporate an Idc residue into custom peptide sequences where an imidazole-bearing side chain is required for structure-function studies. Researchers use this protected amino acid building block to prepare short peptide fragments, analog libraries, and backbone-modified constructs that probe binding interactions, local charge distribution, and hydrogen-bonding patterns. The Boc protection supports stepwise assembly strategies by keeping the amine functionality masked during coupling and fragment condensation steps, enabling downstream purification and characterization of the growing peptide.
2. Peptidomimetic And SAR
Boc-L-Idc-OH is used in medicinal chemistry and chemical biology programs building peptidomimetics that emulate histidine-like chemistry while tuning sterics and side-chain electronics through the Idc motif. Medicinal chemistry teams often incorporate Idc residues into lead optimization campaigns to evaluate how imidazole-containing functionalities influence receptor/ligand recognition, metal coordination behavior, or conformational preferences in solution and in binding assays. As a protected amino acid derivative, it is typically handled as a defined residue for controlled incorporation into analog series, supporting systematic structure-activity relationship (SAR) comparisons across closely related compounds.
3. Solid-Phase And Segment Coupling
Boc-L-Idc-OH supports peptide assembly workflows that rely on protected amino acid residues and controlled deprotection/coupling sequences, including segment condensation approaches used to assemble longer constructs. Peptide manufacturing and research-grade synthesis laboratories use Boc-protected amino acid building blocks to manage reactivity during iterative chain extension, especially when multiple functional groups must remain compatible with the overall protection strategy. This form is particularly useful when the Idc side chain needs to be introduced as a single, well-defined unit while maintaining synthetic control over the amino terminus throughout the assembly of peptide intermediates.
4. Analytical Reference Peptide Synthesis
Boc-L-Idc-OH is also used to prepare defined peptide standards and reference materials for analytical method development, including LC-MS characterization of peptide libraries and verification of sequence integrity in synthetic workflows. Analytical chemistry teams commonly synthesize short Idc-containing peptides as internal benchmarks for retention-time behavior, fragmentation patterns, and identity confirmation when developing or validating workflows for peptide quantification and purity assessment. The protected, residue-specific nature of Boc-L-Idc-OH helps ensure reproducible incorporation of the Idc motif into the reference compound, reducing ambiguity when comparing experimental runs across batches.
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