Boc-D-Cha-OH*DCHA is a protected amino acid derivative in which the amino group of D-configuration 2-amino-2-cyclohexylacetic acid (Cha) is masked as a Boc carbamate, while the carboxylic acid remains present as a free acid (-COOH). The molecule therefore bears both a Boc-protected amine and an unprotected carboxyl functional group, with the cyclohexyl-containing side chain providing a hydrophobic, sterically demanding handle for incorporation into peptide building blocks. In peptide chemistry and chemical biology workflows, this protected analogue is used as a precursor for stepwise assembly of peptides or peptide-like structures where selective deprotection and controlled coupling of the amino acid residue are required, and the "*DCHA" designation indicates the specific Cha stereochemical identity used for synthesis and labeling consistency.
CAT No: CP25539
CAS No:198470-07-4
Synonyms/Alias:Boc-D-Cha-OHDcha;198470-07-4;Boc-D-Cha-OH.DCHA;CTK8E6949;C14H25NO4.C12H23N;6316AH;AKOS015840972;AKOS015914279;RTC-061631;TC-061631;FT-0081109;FT-0643848;K-5803;I14-41171;N-(tert-Butoxycarbonyl)-D-cyclohexylalaninedicyclohexylamine
Chemical Name:N-alpha-(t-Butyloxycarbonyl)-D-cyclohexylalanine dicyclohexylamine
Boc-D-Cha-OH*DCHA is a Boc-protected D-configured amino acid building block featuring a chaulmoogric/cha side-chain motif (Cha) and supplied as a defined stereochemical variant. The Boc group is designed for compatibility with peptide assembly workflows where N-protection is required during coupling and purification, while the side-chain functionality provides a distinct chemical environment for incorporation into modified peptides and medicinal chemistry intermediates.
1. Stereodefined Peptide Building
Boc-D-Cha-OH*DCHA is used by peptide synthesis groups to introduce a stereodefined D-amino acid residue bearing the Cha side chain into protected peptide segments. Researchers performing custom peptide synthesis and peptide library construction rely on the Boc-protected amino acid to maintain backbone protection through iterative coupling/fragment condensation, enabling downstream deprotection and final peptide assembly. This product format is particularly valuable when the D-configuration and the Cha side-chain identity are required to control structure, conformational preferences, and sequence-dependent properties in the resulting peptide.
2. Medicinal Chemistry Intermediates
Boc-D-Cha-OH*DCHA is frequently selected in medicinal chemistry for the preparation of peptidomimetic scaffolds and constrained analogs where a D-amino acid element is incorporated to modulate chemical behavior during lead optimization. Medicinal chemistry and process development teams use Boc-protected amino acid building blocks to assemble advanced intermediates that can be diversified into amide-linked fragments, peptide-like inhibitors, or analog series for structure-activity relationship studies. The Boc-protection strategy supports reliable handling during multi-step synthesis and provides a protected, well-defined input for subsequent functional group transformations.
3. Solution-Phase Segment Condensation
Boc-D-Cha-OH*DCHA supports solution-phase peptide synthesis and segment condensation workflows where N-protection and controlled coupling of amino acid residues are central to reproducible assembly. Custom synthesis providers and research laboratories use Boc-protected amino acids to build longer peptide fragments while minimizing side reactions that can occur with unprotected amines. The D-stereochemistry and Cha side-chain character make this building block a practical choice when the target sequence requires a specific stereochemical identity and a nonstandard side-chain environment, rather than a generic amino acid substitute.
4. Chiral Intermediate Development
Boc-D-Cha-OH*DCHA is also applied as a chiral intermediate for downstream stereochemical elaboration in specialty chemical and pharmaceutical intermediate development. Process chemists and synthetic method developers use Boc-protected D-amino acid inputs to access enantiomerically defined derivatives that can be further functionalized into amide-containing intermediates or advanced building blocks for complex molecule assembly. This product's protected amino functionality and fixed stereochemical identity make it useful when stereochemical fidelity is required across the synthetic sequence.
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