Boc-L-beta-HLeu-OH is a Boc-protected amino acid derivative featuring an L-form β-homoleucine (β-HLeu) backbone, where the side chain is extended relative to leucine to provide an additional methylene unit and a hydrophobic alkyl character. The molecule contains a free carboxylic acid (-COOH) and a Boc-protected amino group (tert-butoxycarbonyl carbamate), which masks the α-amino functionality to control chemoselectivity during stepwise coupling reactions. It is used as a protected building block in peptide synthesis and related amide bond formation workflows, where the Boc group supports sequential assembly while the carboxyl group serves as the acyl functionality for incorporation into larger peptide derivatives.
CAT No: CP25312
CAS No:132549-43-0
Synonyms/Alias:132549-43-0;Boc-L-beta-homoleucine;Boc-beta-Homoleu-OH;(S)-3-((tert-Butoxycarbonyl)amino)-5-methylhexanoicacid;Boc-L-beta-HLeu-OH;(3S)-3-[(tert-butoxycarbonyl)amino]-5-methylhexanoicacid;(S)-3-(Boc-amino)-5-methylhexanoicacid;AmbotzBAA6190;PubChem12105;N-Boc-L-beta-homoleucine;AC1MC55G;14975_ALDRICH;SCHEMBL4934738;14975_FLUKA;CTK8B3012;MolPort-003-793-994;XRVAMBSTOWHUMM-VIFPVBQESA-N;ZINC2572715;ANW-41594;CB-726;MFCD02101665;AKOS015900923;BL720-1;AJ-42077;AK-90329
Chemical Name:N-beta-(t-Butyloxycarbonyl)-L-homoleucine
Boc-L-beta-HLeu-OH is a Boc-protected amino acid derivative built on the β-homoleucine (β-HLeu) side-chain framework, providing a protected primary amino group for controlled peptide assembly. The β-substituted aliphatic side chain increases steric bulk relative to standard leucine-like residues, making it useful for constructing non-canonical peptide architectures and conformationally distinct segments. As a Boc-protected building block, it is commonly selected for BOC-compatible peptide synthesis workflows and for preparing peptide intermediates where the amino group must remain masked during coupling steps.
1. Boc-Compatible Peptide Synthesis
Boc-L-beta-HLeu-OH is used by peptide synthesis groups to incorporate a β-homoleucine residue into peptide chains under Boc-based protection strategies. Researchers preparing modified peptides for structure-activity relationship studies or for mapping how β-substitution affects backbone/side-chain presentation often choose this building block because the Boc group provides reliable amine protection during coupling and assembly of the peptide sequence. The β-HLeu side chain is particularly valuable when steric and hydrophobic characteristics of a leucine-like residue need to be tuned through β-position substitution, enabling access to peptide variants that differ in local packing and synthetic handle spacing.
2. Non-Canonical Residue Incorporation
Boc-L-beta-HLeu-OH supports peptide and peptidomimetic development where non-standard amino acid residues are introduced to probe structure-property relationships. Chemical biology and medicinal chemistry teams frequently use β-substituted aliphatic residues to modulate conformational preferences, side-chain reach, and overall physicochemical character of peptide scaffolds. By using a Boc-protected amino acid building block, developers can reliably position the β-HLeu residue within larger synthetic constructs, including longer segments assembled by fragment condensation, to generate libraries of analogs for downstream characterization such as chromatography-based profiling and stability-oriented studies.
3. Peptide Intermediate Building Block
Boc-L-beta-HLeu-OH is also employed as a practical intermediate for producing protected peptide fragments and defined coupling partners in custom peptide manufacturing workflows. In segment condensation approaches, the Boc-protected amino functionality helps maintain compatibility with peptide assembly steps that require orthogonal control of reactive groups, allowing the β-HLeu residue to be introduced at a planned stage of synthesis. This makes the building block useful for laboratories that routinely generate mid-chain intermediates for later completion of the full peptide, where consistent residue identity and protection state are required for reproducible downstream purification and analytical characterization.
4. Analytical Reference Peptide Development
Boc-L-beta-HLeu-OH is used in the preparation of defined peptide standards and reference materials that contain β-homoleucine within the sequence. Analytical chemistry teams developing LC-MS methods or peptide characterization workflows often require authentic, sequence-defined materials to confirm retention behavior, fragmentation patterns, and identity of peptide fragments that include β-substituted residues. The Boc-protected building block enables controlled synthesis of these reference peptides, supporting method verification and routine quality checks in peptide research and development settings where non-canonical residues are part of the target sequence space.
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