Boc-4,5-dehydro-Leu-OH · DCHA is a Boc-protected, non-proteinogenic dehydro amino acid derivative based on a leucine skeleton, featuring a 4,5-dehydro (alkene) substitution on the side-chain and a free carboxylic acid for peptide-coupling chemistry. The molecule bears a tert-butoxycarbonyl (Boc) protecting group on the amino functionality while the side-chain unsaturation and the amino acid backbone provide defined sites for chemoselective transformations and controlled reactivity during stepwise synthesis, and the "· DCHA" indicates formation as a salt with dicyclohexylamine. In research workflows, this protected amino acid salt is used as a precursor for incorporating the dehydro-leucine motif into peptide or peptide-like structures via protected-amino-acid coupling strategies, supporting structure-activity studies, conformational probing, and chemical biology labeling where an unsaturated side-chain handle is required.
CAT No: CP27557
CAS No:87720-54-5
Synonyms/Alias:87720-54-5;BOC-4,5-DEHYDRO-LEU-OHDCHA;AC1MBSDY;11578_ALDRICH;11578_FLUKA;MolPort-003-725-636;BOC-4,5-DEHYDRO-LEU-OHDCHA;1385AF;KM2548;MFCD00237524;AKOS025312267;Boc-4,5-dehydro-L-leu-OH.DCHA;Boc-4,5-dehydro-Leu-OHdicyclohexylaminesalt;Boc-4,5-dehydro-L-leucinedicyclohexylaminesalt;Boc-4,5-dehydro-Leu-OHdicyclohexylammoniumsalt;Boc-4,5-dehydro-Leu-OH(dicyclohexylammonium)salt;Boc-4,5-dehydro-L-leucine(dicyclohexylammonium)salt;(S)-2-(Boc-amino)-4-methyl-4-pentenoicaciddicyclohexylaminesalt;(2S)-2-[(tert-butoxycarbonyl)amino]-4-methylpent-4-enoicacid;dicha;(S)-2-(Boc-amino)-4-methyl-4-pentenoicacid(dicyclohexylammonium)salt;N-cyclohexylcyclohexanamine;(2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-enoicacid
Boc-4,5-dehydro-Leu-OH · DCHA is a Boc-protected dehydro-leucine amino acid derivative provided as a dicyclohexylamine (DCHA) salt, combining an N-Boc peptide synthesis handle with an unsaturated side-chain motif that can influence peptide conformation and reactivity during downstream assembly. The product is commonly used in peptide chemistry workflows where a constrained, non-standard leucine analog is required for structure-property studies, fragment synthesis, and the preparation of modified peptide intermediates. Its salt form is selected to support practical handling and consistent performance in peptide building-block workflows.
1. Modified Peptide Synthesis
Boc-4,5-dehydro-Leu-OH · DCHA is used by peptide chemists to incorporate a dehydro-leucine residue into custom peptides and peptide libraries, enabling access to non-proteinogenic analogs for conformational and structure-activity relationship studies. The N-Boc protection supports standard peptide assembly strategies, while the 4,5-dehydro motif provides a distinct side-chain unsaturation compared with saturated leucine, which can be leveraged when designing peptides with altered backbone/side-chain geometry. Researchers developing peptide fragments for subsequent coupling steps often select this building block because it integrates directly into protected-amino-acid workflows used for rapid synthesis of modified sequences.
2. Peptide Fragment And Intermediate Building
Boc-4,5-dehydro-Leu-OH · DCHA is frequently employed in the preparation of protected peptide fragments and advanced intermediates for solution-phase or stepwise segment condensation workflows. Because the compound is supplied as an N-Boc amino acid derivative, it functions as a reliable monomeric unit for building sequence-defined intermediates that can be carried forward into larger constructs. Medicinal chemistry and process development teams use such intermediates to streamline the synthesis of non-natural peptide components, particularly when the dehydro-leucine residue is needed as a defined structural element for downstream derivatization, purification, or final assembly.
3. Conformational Probe Development
Boc-4,5-dehydro-Leu-OH · DCHA is used in chemical biology and peptide research programs that require non-standard amino acid content to act as a conformational probe within peptide scaffolds. The unsaturated 4,5-dehydro side-chain provides a structural perturbation relative to natural leucine, supporting studies that evaluate how local geometry impacts peptide folding tendencies, aggregation behavior, and recognition by binding partners in vitro. Teams conducting structure-focused peptide design often choose this building block to introduce a defined, residue-level modification that can be compared across analog series while maintaining a protected, synthesis-friendly format for consistent incorporation.
4. Pharmaceutical Intermediate Research
Boc-4,5-dehydro-Leu-OH · DCHA is also applied in pharmaceutical intermediate development when non-natural amino acid derivatives are needed as defined inputs for constructing peptide-like candidates, peptidomimetics, or key synthetic fragments. Process and synthetic chemistry groups use the N-Boc protected form to maintain compatibility with protected-building-block supply chains and to support scalable intermediate handling during route development. The DCHA salt form is selected for practical reagent management in industrial and contract synthesis environments, where consistent physical form and handling characteristics can matter during multistep assembly of specialized peptide intermediates.
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