Boc-DL-Ile-OH is a protected amino acid derivative of isoleucine in which the amino group is carbamate-protected with a tert-butoxycarbonyl (Boc) group, and the molecule bears both an amino acid backbone and a free carboxylic acid (-COOH). The side chain corresponds to the isoleucine isopropyl-substituted sec-butyl functionality, and the "DL" designation indicates a racemic mixture of stereoisomers at the α-carbon while the Boc group masks the primary amine to reduce undesired side reactions during coupling. Boc-DL-Ile-OH is used as a stepwise building block in peptide synthesis and as a precursor for preparing more complex isoleucine-containing amino acid derivatives through controlled amide bond formation at the protected amino terminus.
CAT No: CP26218
CAS No:116194-21-9
Synonyms/Alias:Boc-L-isoleucine;13139-16-7;Boc-Ile-OH;N-Boc-L-isoleucine;N-(tert-Butoxycarbonyl)-L-isoleucine;Boc-DL-Ile-OH;Boc-L-Ile-OH;BOC-ISOLEUCINE;(2S,3S)-2-((tert-Butoxycarbonyl)amino)-3-methylpentanoicacid;QJCNLJWUIOIMMF-YUMQZZPRSA-N;MFCD00038324;SBB028561;(TERT-BUTOXYCARBONYL)-L-ISOLEUCINE;N-tert-Butoxycarbonyl-L-isoleucine;(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-methylpentanoicacid;(2S,3S)-2-{[(Tert-Butoxy)Carbonyl]Amino}-3-MethylpentanoicAcid;116194-21-9;L-Isoleucine,N-[(1,1-dimethylethoxy)carbonyl]-;tert-Butyloxycarbonyl-L-isoleucine;(2S,3S)-2-[(tert-butoxy)carbonylamino]-3-methylpentanoicacid;Boc-L-isoleucinehemihydrate;(2S,3S)-2-([(TERT-BUTOXY)CARBONYL]AMINO)-3-METHYLPENTANOICACID;N-alpha-t-BOC-L-ISOLEUCINE;Boc-Ile-OHhydrate;Boc-(L)-isoleucine
Boc-DL-Ile-OH is a Boc-protected, DL-configured isoleucine building block designed for peptide and peptidomimetic synthesis workflows. The side chain of isoleucine provides a hydrophobic, branched alkyl functionality that is commonly exploited for controlling sequence composition and local sterics in synthetic peptides. As a racemic (DL) protected amino acid, it is frequently selected when stereochemical uniformity is not required or when screening and intermediate preparation benefit from using a single commercially available stereochemical mixture.
1. Solution-Phase Peptide Coupling
Boc-DL-Ile-OH is used in solution-phase peptide synthesis where a Boc-protected amino acid segment is incorporated into growing peptide chains through standard amide bond-forming strategies. Synthetic chemists and custom peptide manufacturing groups choose the Boc protection pattern to match their established deprotection and coupling sequence, particularly when they prefer Boc-compatible workflows for assembling short to medium-length peptides and peptide fragments. The isoleucine side chain contributes hydrophobic character and conformational influence, supporting the preparation of peptide intermediates used in structure-activity relationship studies and fragment-based optimization.
2. Solid-Phase Peptide Segment Building
Boc-DL-Ile-OH is also applied as an amino acid building block for peptide assembly strategies that incorporate Boc-protected residues as part of protected segment construction and library synthesis. Peptide chemists use racemic DL material when generating peptide libraries or intermediate sets where the stereochemical outcome is intentionally averaged, such as early-stage sequence exploration, process development, or comparative studies of side-chain packing effects. The branched isoleucine alkyl group helps define hydrophobic microenvironments in the target sequences, which is often relevant for producing peptide scaffolds used in chemical biology probe development and binding-assay reagent generation.
3. Peptidomimetic Intermediate Preparation
Boc-DL-Ile-OH serves as a practical intermediate for preparing peptidomimetic building blocks and protected amino acid derivatives that retain the isoleucine side chain while enabling downstream functionalization. Medicinal chemistry teams and specialty synthesis groups commonly use this type of protected amino acid to create stereochemically mixed intermediates for exploring how hydrophobic, branched residues affect conformational preferences and structure-activity relationships in non-natural peptide analogs. The Boc-protected amino functionality provides a controlled handle for subsequent transformations, allowing the material to be routed into downstream coupling, fragment elaboration, or protected scaffold construction.
4. Analytical Reference Material Development
Boc-DL-Ile-OH is frequently employed in analytical method development and reference preparation for workflows that require a protected amino acid standard or a defined synthetic precursor for method qualification. Analytical chemistry laboratories use racemic Boc-protected isoleucine to generate calibration or system suitability materials in studies involving protected amino acid handling, peptide fragment analysis, and impurity profiling during peptide process development. The presence of the Boc group and the isoleucine side chain makes it a convenient, chemically well-defined precursor for validating chromatographic separation and mass-based detection of protected amino acid species and related intermediates.
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