Boc-alpha-Et-L-Ala-OH is a protected amino acid derivative in which the amino group of an L-alanine analogue bearing an alpha-ethyl substituent is masked with a Boc (tert-butoxycarbonyl) protecting group. The molecule contains a free carboxylic acid functionality and a substituted alpha-carbon that supports the stereochemical configuration indicated by the L designation, while the side chain corresponds to an alanine-type methyl group. As a stepwise peptide-synthesis building block, the Boc protection supports chemoselective handling of the amino functionality during coupling to form peptide bonds, and the alpha-ethyl substitution can be used in structure-activity or conformational studies involving modified amino acid residues.
CAT No: CP25242
CAS No:123254-58-0
Synonyms/Alias:(R)-2-((tert-Butoxycarbonyl)amino)-2-methylbutanoicacid;123254-58-0;(R)-2-(tert-butoxycarbonylamino)-2-methylbutanoicacid;Boc-D-isovaline;SCHEMBL1979477;MolPort-008-155-788;SHZXLTCEPXVCSV-SNVBAGLBSA-N;ZINC34623329;AKOS025117414;AK163820;(R)-2-Methyl-2-(tert-butoxycarbonylamino)butyricacid;(2R)-2-(tert-butoxycarbonylamino)-2-methyl-butanoicacid
Chemical Name:(R)-2-(t-Butyloxycarbonylamino)-2-methylbutanoic acid
Boc-alpha-Et-L-Ala-OH is a Boc-protected, L-configured alanine derivative bearing an ethyl substituent on the alpha position, making it a non-proteinogenic amino acid building block for peptide and peptidomimetic construction. The N-terminus is protected as a Boc carbamate, supporting its use as a protected amino acid intermediate in controlled coupling workflows. This structure is commonly selected when developers need a sterically and stereochemically defined, alpha-substituted residue to probe conformation, backbone effects, or to access specialized peptidomimetic scaffolds.
1. Peptidomimetic Building Blocks
Boc-alpha-Et-L-Ala-OH is used by medicinal chemistry and chemical biology groups to assemble peptidomimetic sequences where an alpha-ethyl substitution is introduced to modulate backbone properties and structure. Researchers incorporate this residue into short peptide analogs during custom peptide synthesis to generate analog panels for structure-property studies, including conformational bias and backbone steric effects. The Boc-protected amino functionality supports stepwise assembly strategies that require stable handling of the amino terminus during chain elongation.
2. Protected Amino Acid Intermediate
Boc-alpha-Et-L-Ala-OH serves as a protected amino acid intermediate for downstream synthesis of specialized amino acid derivatives and peptide segments. Process and development chemists use it as a defined, stereochemically consistent building block to prepare coupling-ready fragments for solution-phase or automated segment assembly workflows. The presence of the Boc group provides a practical protection strategy that helps maintain the amino functionality during intermediate transformations, enabling reliable incorporation into larger synthetic targets.
3. Backbone-Modified Peptide Synthesis
Boc-alpha-Et-L-Ala-OH is applied in peptide synthesis workflows aimed at generating backbone-modified peptides for SAR development and chemical biology tool generation. Peptide chemists select the alpha-substituted alanine derivative when they want to compare sequences that differ specifically at the backbone substitution pattern while keeping other side-chain features consistent. The Boc-protected N-terminus aligns with standard protected-residue handling practices used to build modified peptides with controlled protection and deprotection sequences.
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