Boc-beta-(2-thienyl)-DL-Ala-OH is a protected amino acid derivative featuring a Boc-protected alpha-amino group and a beta-(2-thienyl) substituted alanine backbone, placing it in the class of modified amino acids used for peptide and building-block synthesis. The molecule contains a free carboxylic acid (-COOH) and a side chain bearing a 2-thienyl aromatic substituent, with the "DL" designation indicating a racemic mixture at the stereocenter(s) implied by the alanine framework. In synthesis, the Boc group provides chemoselective control over the amine during stepwise coupling strategies, while the thiophene-bearing beta substituent functions as a structural handle for preparing peptides and analogues with aryl-containing motifs for structure-activity studies and chemical biology labeling workflows.
CAT No: CP27473
CAS No:78512-39-7
Synonyms/Alias:78512-39-7;2-((tert-Butoxycarbonyl)amino)-3-(thiophen-2-yl)propanoicacid;2-[(TERT-BUTOXYCARBONYL)AMINO]-3-(THIOPHEN-2-YL)PROPANOICACID;SCHEMBL844317;BOC-BETA--DL-ALA-OH;AC1NN131;CTK8J3632;MolPort-020-349-442;OJLISTAWQHSIHL-UHFFFAOYSA-N;2292AC;N-Boc-beta-(2-thienyl)-DL-alanine;AKOS009157548;PS-3745;TRA0068052;BOC-BETA-(2-THIENYL)-DL-ALA-OH;AK116352;AM032893;HE023980;KB-220005;3-(Thien-2-yl)-L-alanine,N-BOCprotected;I09-0386;3B3-068510;2-{[(tert-butoxy)carbonyl]amino}-3-(thiophen-2-yl)propanoicacid;2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-thiophen-2-ylpropanoicacid
Boc-beta-(2-thienyl)-DL-Ala-OH is a Boc-protected, DL-configured alanine derivative bearing a beta-(2-thienyl) substituent, combining a protected amino functionality with a heteroaryl side chain. This structure is commonly leveraged as a stereochemically mixed amino acid building block for assembling modified peptides and peptidomimetic scaffolds where a thiophene-containing beta-substitution is used to tune sterics and electronics. In synthetic workflows, the Boc group supports controlled amide formation during peptide assembly and intermediate preparation.
1. Modified Peptide Building Blocks
Boc-beta-(2-thienyl)-DL-Ala-OH is used by custom peptide synthesis groups to introduce a thiophene-bearing beta-substituted alanine residue into sequence-defined peptides. The Boc-protected amino group enables downstream coupling strategies in solution-phase or segment-condensation workflows, while the beta-(2-thienyl) motif provides a hydrophobic, heteroaryl handle that can influence conformational preferences and local physicochemical properties of the resulting peptide. Researchers developing structure-activity relationship (SAR) panels for peptidomimetic leads often select this type of residue to systematically vary aromatic content and side-chain topology without changing the peptide backbone framework.
2. Peptidomimetic SAR Intermediates
Boc-beta-(2-thienyl)-DL-Ala-OH serves as a practical pharmaceutical intermediate for medicinal chemistry programs that convert amino acid-derived fragments into peptidomimetic or constrained analogs. The presence of a heteroaryl (2-thienyl) substituent at the beta position supports incorporation into larger scaffolds where aromatic electronics and ring heteroatoms are used to modulate interactions in binding assays and off-target profiling workflows. Because the material is provided as a DL mixture, it is often selected when the development strategy prioritizes rapid analog generation and comparative SAR mapping over strict stereochemical uniformity at the residue level, enabling efficient parallel synthesis of thiophene-containing variants.
3. Heteroaryl-Containing Fragment Assembly
Boc-beta-(2-thienyl)-DL-Ala-OH is frequently employed in fragment-based assembly of modified amide-rich structures, including hybrid peptide-small molecule conjugates and heteroaryl-functionalized linkers. The thiophene ring offers a chemically stable aromatic motif that can be carried through multi-step synthesis into final intermediates for subsequent coupling, diversification, or scaffold elaboration. In industrial and translational chemistry settings, this building block is used to standardize the introduction of a beta-(2-thienyl) unit across multiple batches, supporting reproducible synthesis of analog libraries where consistent heteroaryl placement is required for downstream characterization by LC-MS and NMR.
4. Analytical Reference Material Development
Boc-beta-(2-thienyl)-DL-Ala-OH is also used as a defined synthetic reference for method development and characterization of thiophene-containing peptide intermediates. Analytical chemistry teams preparing LC-MS workflows, purification standards, or impurity profiling panels rely on well-characterized amino acid derivatives to confirm retention behavior and mass spectral signatures for beta-(2-thienyl) substituted alanine fragments. The Boc-protected form further provides a consistent functional-group pattern during derivatization and analytical handling, which can simplify comparison across synthesis runs when monitoring coupling efficiency, intermediate stability, and the presence of related side products.
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