Boc-D-allo-isoleucine is a protected amino acid derivative in which the amino group is protected as a Boc (tert-butoxycarbonyl) carbamate and the side chain corresponds to an allo-configured isoleucine framework, making it a stereodefined, non-free amino acid suitable for peptide coupling chemistry. The molecule contains both a Boc-protected α-amino functionality and a free carboxylic acid, with the allo stereochemical relationship embedded in the substituted carbon skeleton and the isoleucine-like branched alkyl side chain providing hydrophobic character. In synthesis, it is employed as a stepwise building block for protected amino acid incorporation into peptides, where the Boc group helps control chemoselectivity by reducing undesired reactions of the amino functionality during amide bond formation.
CAT No: CP01207
CAS No:55780-90-0
Synonyms/Alias:(S)-Methyl6-amino-2-((tert-butoxycarbonyl)amino)hexanoate;55757-60-3;Boc-L-Lysinemethylester;(S)-methyl6-amino-2-(tert-butoxycarbonylamino)hexanoate;Boc-L-Lysinemethylester;SCHEMBL1904291;CTK8B4911;MolPort-023-223-295;UEBNVLLIWJWEKV-VIFPVBQESA-N;ZINC2555029;ANW-46670;AKOS015998685;AM82994;RTR-019663;AJ-39676;AK-84885;KB-48346;SC-20749;(tert-butoxycarbonyl)-L-lysinemethylester;ST24020865
Boc-D-allo-isoleucine is a protected D-configured allo-isoleucine amino acid building block bearing a Boc (tert-butoxycarbonyl) group on the amino functionality. The allo stereochemical relationship at the side-chain-bearing stereocenter makes it a stereochemically distinct isoleucine analogue, which is valuable when stereochemical control is required in peptide and peptidomimetic sequences. As a Boc-protected amino acid, it is commonly handled as a peptide synthesis intermediate where the protected amine supports controlled assembly of amide bonds under standard protected-amino-acid workflows.
1. Boc-Based Peptide Coupling
Boc-D-allo-isoleucine is used in custom peptide synthesis workflows where a D-allo isoleucine residue is required for stereochemical probing, sequence optimization, or conformational studies. Peptide chemists select this Boc-protected building block to introduce the allo stereochemistry at the residue level while maintaining an amine protection state compatible with routine coupling/segment assembly strategies. The protected form supports predictable downstream handling during stepwise chain construction, enabling incorporation into short peptides, cyclic precursors, and stereodefined analog libraries developed for structure-activity relationship work.
2. Stereodefined Peptidomimetic Design
Boc-D-allo-isoleucine is frequently incorporated into peptidomimetic and non-natural peptide analogue development programs aimed at mapping how side-chain stereochemistry influences backbone conformation and local interactions. Medicinal chemistry and chemical biology groups use this stereochemically constrained amino acid building block to generate analog panels in which the residue stereochemistry is systematically varied, supporting SAR campaigns and mechanistic studies that rely on defined stereochemical identity. The Boc-protected amino acid format streamlines integration into synthetic routes that assemble amide-linked scaffolds with controlled stereocenters.
3. Protected Amino Acid Intermediate Synthesis
Boc-D-allo-isoleucine serves as a practical protected-amino-acid intermediate for downstream derivatization steps that require a protected amino functionality during multi-step manufacturing. Pharmaceutical intermediate development teams and specialty synthesis groups use this building block as a defined stereochemical precursor for preparing additional protected derivatives or for producing residue-containing fragments used in larger assembly workflows. The Boc protection pattern helps maintain the amino group in a controlled state during intermediate elaboration, supporting reliable purification and handling across sequential synthetic operations.
4. Analytical Reference Material Preparation
Boc-D-allo-isoleucine is also used in analytical method development and reference standard preparation where stereochemically defined amino acid residues are needed for characterization of peptide intermediates and final products. Analytical chemistry groups employ this protected, stereodefined building block to support method verification for identity and composition checks in peptide synthesis pipelines, including workflows that compare stereochemical outcomes across analog series. The defined D-allo stereochemistry and Boc-protected identity make it useful when distinguishing stereochemical variants in research-grade quality control and characterization strategies.
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