Boc-L-2-aminobutyric acid is an N-Boc-protected amino acid derivative featuring the 2-aminobutyric acid backbone with an L-stereochemical configuration and a side chain that terminates in a terminal methyl group. The molecule contains both an amino functionality masked as a carbamate by the tert-butoxycarbonyl (Boc) group and a free carboxylic acid, enabling controlled chemoselectivity by suppressing amine reactivity during peptide-coupling steps. In peptide chemistry, it is used as a protected amino acid building block to introduce a 2-aminobutyl side-chain motif into peptide chains via standard coupling strategies that require an unreactive amino group and a carboxyl group for bond formation.
CAT No: CP02904
CAS No:34306-42-8
Synonyms/Alias:Boc-Abu-OH;34306-42-8;Boc-L-2-aminobutyricacid;(S)-2-((TERT-BUTOXYCARBONYL)AMINO)BUTANOICACID;Boc-2-Abu-OH;Boc-L-2-aminobutanoicacid;L-2-(BOC-AMINO)BUTYRICACID;ST51014916;(S)-2-(Tert-butoxycarbonylamino)butyricacid;(2S)-2-[(tert-butoxycarbonyl)amino]butanoicacid;(S)-2-(Boc-amino)butyricacid;(S)-2-[(tert-butoxycarbonyl)amino]butanoicacid;BOC-homoalanine;PubChem18942;AC1MBSF4;15533_ALDRICH;SCHEMBL835996;15533_FLUKA;MolPort-002-344-005;PNFVIPIQXAIUAY-LURJTMIESA-N;ACT10804;ZINC2384824;CB-833;EBD2202708;(S)-2-t-Butoxycarbonylaminobutanoicacid
Boc-L-2-aminobutyric acid is an N-Boc-protected, L-configured amino acid building block featuring a secondary amino acid backbone with an aliphatic side chain that supports incorporation into peptide segments and peptidomimetic scaffolds. The Boc group provides acid-labile protection of the amino functionality, making the reagent a practical intermediate for controlled peptide assembly and for preparing defined amino acid derivatives for medicinal chemistry programs. Its stereochemical consistency and protected amine format make it well aligned with standard coupling workflows used by peptide synthesis and pharmaceutical intermediate development teams.
1. Peptide Segment Building
Boc-L-2-aminobutyric acid is used as a protected amino acid building block for constructing peptide segments where a 2-aminobutyric acid residue is required with defined stereochemistry. Peptide synthesis groups in custom peptide manufacturing, academic peptide chemistry, and medicinal chemistry teams rely on Boc-protected amino acids to streamline stepwise assembly and to maintain compatibility with iterative coupling and deprotection strategies during fragment condensation. The aliphatic side chain contributes to local hydrophobicity and conformational preferences in the resulting peptide or peptidomimetic, which is often leveraged during lead optimization and structure-activity relationship studies.
2. Peptidomimetic And SAR Intermediates
Boc-L-2-aminobutyric acid serves as a practical intermediate for preparing peptidomimetic structures and defined amino acid derivatives used in SAR workflows. Medicinal chemistry researchers incorporate this residue into constrained or analog series to evaluate how side-chain size and backbone stereochemistry influence binding-related properties and overall structure. Because the amine is protected as a Boc carbamate, the reagent can be handled and coupled under controlled conditions to generate analogs with consistent composition, supporting parallel synthesis campaigns where reproducible building blocks are essential.
3. Pharmaceutical Intermediate Synthesis
Boc-L-2-aminobutyric acid is frequently used in the downstream preparation of protected amino acid intermediates for pharmaceutical intermediate development. Process chemistry and specialty synthesis teams select Boc-protected amino acids to manage functional-group compatibility across multi-step sequences, especially when downstream transformations require a stable, protected amine handle until the appropriate stage of the synthesis. The reagent's defined L-stereochemistry and protected format make it a reliable input for assembling larger, structurally defined intermediates used in the creation of candidate molecules and research-grade reference compounds.
4. Amino Acid Derivative Preparation
Boc-L-2-aminobutyric acid is also used to generate additional amino acid derivatives where the Boc-protected amine is a convenient protected functional group for further functionalization. Chemical biology and analytical chemistry groups preparing standards, labeled or derivatized fragments, or specialized building blocks for downstream coupling steps often prefer Boc-protected amino acids to control reactivity and to prevent premature amine participation. This makes the reagent useful when a defined amino acid unit must be carried through synthesis as a protected intermediate before conversion into the final coupled form.
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