Boc-beta-(2-quinolyl)-D-Ala-OH is a protected, non-natural amino acid derivative featuring a beta-(2-quinolyl) substituent on the alanine backbone and a D-configured stereocenter as indicated by the name. The molecule bears an N-terminal Boc (tert-butoxycarbonyl) protecting group while retaining a free carboxylic acid and a side chain that contains a quinoline aromatic heterocycle, providing a rigid, hydrophobic, and heteroaromatic functionality for chemical recognition and conjugation. In peptide and amino acid derivative synthesis, this protected analogue is used as a building block to introduce a quinolyl-bearing beta-substituted alanine residue into larger peptide frameworks and to support structure-activity studies, molecular labeling, or materials-oriented conjugation where the quinoline ring serves as a functional motif.
CAT No: CP26496
CAS No:170157-64-9
Synonyms/Alias:Boc-D-Ala(2'-quinolyl)-OH;170157-64-9;Boc-beta-(2-quinolyl)-D-Ala-OH;AC1ODTTG;CTK8F0140;ZINC2567262;6285AH;AKOS022181582;AJ-41378;AK-62621;RT-011719;I14-32616;(R)-2-((tert-Butoxycarbonyl)amino)-3-(quinolin-2-yl)propanoicacid;(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-quinolin-2-ylpropanoicacid
Boc-beta-(2-quinolyl)-D-Ala-OH is a Boc-protected, D-configured β-substituted alanine derivative where the side chain bears a 2-quinolyl substituent, providing a rigid, aromatic handle for medicinal chemistry and peptide-based structure studies. The presence of the Boc group makes it a protected amino acid building block commonly handled in peptide synthesis workflows, while the quinoline motif supports downstream functionalization and analytical detectability through aromatic chromophore chemistry.
1. Peptide Building Block Incorporation
Boc-beta-(2-quinolyl)-D-Ala-OH is used as a protected amino acid building block for custom peptide synthesis where incorporation of a D-amino acid is required for conformational control and proteolysis-resistance design strategies. Peptide synthesis teams in academic peptide chemistry groups and peptide CROs select this derivative when they need a β-aryl substituted residue that can influence local backbone geometry and side-chain orientation. The Boc-protected amino functionality supports standard protected-amino-acid coupling workflows, enabling assembly of peptides that contain a quinoline-bearing residue for subsequent derivatization or for creating aromatic-rich peptide segments used in binding and structure-activity relationship studies.
2. Medicinal Chemistry SAR Intermediates
Boc-beta-(2-quinolyl)-D-Ala-OH is frequently positioned as a pharmaceutical intermediate for medicinal chemistry programs that explore peptidomimetics and constrained amino-acid analogs. Medicinal chemistry groups use this compound to prepare analog libraries where a D-configuration and a quinoline-containing β-substituent are built into larger scaffolds, including peptide-like fragments and side-chain-modified inhibitors or receptor-binding probes. The quinoline ring provides a chemically stable aromatic motif that can be carried through to later steps for scaffold diversification, while the protected amino acid format supports controlled downstream coupling into larger structures during lead optimization.
3. Aromatic Labeling And Derivatization
Boc-beta-(2-quinolyl)-D-Ala-OH serves as a practical aromatic precursor for workflows that require introduction of a quinoline-containing moiety into peptides, small-molecule conjugates, or analytical standards. Chemical biology and materials chemistry laboratories use the 2-quinolyl substituent as a handle for designing conjugates where aromatic functionality is leveraged for detection, tagging, or further chemical modification in later stages. Because the amino group is protected, researchers can sequence the installation of the residue into a target molecule and then perform subsequent derivatization steps on the quinoline-bearing scaffold as part of multistep labeling or assay-development pipelines.
4. Analytical Standard For LC-MS Studies
Boc-beta-(2-quinolyl)-D-Ala-OH is also used in analytical method development and reference material preparation for LC-MS-based workflows that monitor quinoline-containing peptide fragments or amino-acid-derived species. Analytical chemistry teams use the compound as a defined, structurally specific standard when developing extraction, calibration, and identification strategies for β-quinolyl substituted D-alanine motifs in complex mixtures. The combination of a protected amino acid format and a distinctive quinoline aromatic signature helps ensure consistent mass-based identification of the target residue or its derivatives during method validation and troubleshooting in peptide and peptidomimetic analysis.
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