Boc-beta-(2-quinolyl)-Ala-OH is a Boc-protected, beta-substituted alanine derivative in which the alanine backbone bears a 2-quinolyl substituent at the beta position, classifying it as a non-standard amino acid used for peptide and small-molecule construction. The molecule contains a free carboxylic acid (-COOH) and an N-terminus protected by a Boc (tert-butoxycarbonyl) group, while the quinolyl side-chain provides an aromatic heterocycle with basic nitrogen character and distinct electronic and hydrophobic features. In synthesis, this protected amino acid is employed as a building block for incorporating a beta-quinolyl alanine motif into peptides or peptide-like structures via stepwise coupling strategies, and it can also serve as a precursor for preparing quinolyl-functionalized amino acid derivatives for structure-activity studies and chemical labeling workflows.
CAT No: CP26447
CAS No:161453-37-8
Synonyms/Alias:Boc-beta-(2-quinolyl)-Ala-OH;161453-37-8;AC1ODTSY;SCHEMBL2300113;ZINC2567255;6284AH;AKOS015908771;AJ-41373;AK-62620;AM001658;I14-34522;(S)-2-((tert-Butoxycarbonyl)amino)-3-(quinolin-2-yl)propanoicacid;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-quinolin-2-ylpropanoicacid;(2S)-2-[(TERT-BUTOXYCARBONYL)AMINO]-3-(QUINOLIN-2-YL)PROPANOICACID
Boc-beta-(2-quinolyl)-Ala-OH is a Boc-protected alanine derivative bearing a beta-(2-quinolyl) substituent, providing a conformationally and electronically distinctive side chain for peptide and peptidomimetic construction. The presence of the Boc group supports controlled use in protected-amino-acid workflows, while the quinoline (2-quinolyl) motif offers a rigid aromatic handle that can be leveraged for structure-property studies and downstream functionalization strategies. This reagent is typically handled by peptide chemistry teams and medicinal chemistry groups developing modified peptide segments or specialized amino acid building blocks for SAR and chemical biology tool development.
1. Modified Peptide Segment Building
Boc-beta-(2-quinolyl)-Ala-OH is used as a protected amino acid building block to introduce a quinoline-bearing alanine unit into custom peptides during peptide synthesis workflows. Researchers in peptide chemistry and medicinal chemistry employ this type of residue to create analogs with altered aromatic character, steric profile, and electronic features compared with canonical alanine-containing sequences. The Boc protection pattern supports incorporation within protected-residue assembly strategies, enabling consistent handling of the amino functionality while the beta-(2-quinolyl) substituent remains available for the intended downstream peptide design goals.
2. Peptidomimetic And SAR Studies
Boc-beta-(2-quinolyl)-Ala-OH supports structure-activity relationship (SAR) and peptidomimetic development where an aromatic quinoline moiety is introduced to probe binding-site interactions, conformational preferences, or physicochemical trends. Medicinal chemistry groups often choose this kind of non-standard residue to systematically vary aromatic content and substitution patterns while keeping the peptide backbone context comparable across analog series. The quinoline ring provides a chemically stable aromatic scaffold that can be used to generate focused libraries of modified peptide fragments for lead optimization and mechanistic chemistry investigations.
3. Fluorescent And Aromatic Probe Design
Boc-beta-(2-quinolyl)-Ala-OH is applied in chemical biology and analytical chemistry contexts where aromatic quinoline motifs are incorporated as intrinsic or appended reporter elements within peptides. Researchers use quinoline-bearing residues to create peptide constructs that can serve as fluorescence-active tags, environmental polarity reporters, or spectroscopic probes when integrated into a larger molecular framework. The beta-(2-quinolyl) substitution offers a defined aromatic location within the peptide sequence, which is valuable for designing experiments that rely on consistent placement of the chromophore relative to other functional groups in the probe.
4. Pharmaceutical Intermediate For Specialized Residues
Boc-beta-(2-quinolyl)-Ala-OH is also used as a pharmaceutical intermediate building block for manufacturing modified peptide fragments and specialized amino acid derivatives used in research-grade development pipelines. Process and development chemists select this reagent when a quinoline-substituted alanine unit is required as a defined input for downstream assembly steps, enabling controlled generation of complex, sequence-defined intermediates. The combination of a protected amino functionality with a rigid aromatic substituent makes it a practical starting material for preparing custom, non-standard residues that are difficult to obtain from standard amino acid feedstocks.
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