Cyclohexylstatine is a non-proteinogenic amino acid derivative featuring a statine-like scaffold with a cyclohexyl-substituted side chain, classifying it within the amino acid family used for peptidomimetic design. The molecule contains both an amino group and a carboxyl functional group, and its bulky, hydrophobic cyclohexyl side chain provides a conformationally constrained, sterically demanding residue for incorporation into synthetic peptides or peptide analogues. Cyclohexylstatine is employed in chemical biology and structure-activity studies where modified amino acid stereochemistry and side-chain topology are used to probe protease/peptidase substrate recognition and to prepare labeled or derivatized peptidomimetics for analytical and synthesis workflows.
CAT No: CP26160
CAS No:105192-90-3
Synonyms/Alias:(3S,4S)-4-amino-5-cyclohexyl-3-hydroxypentanoicacid;ACHPA,(3S,4S)-4-Amino-5-cyclohexyl-3-hydroxy-pentanoicacid;105192-90-3;AC1NRAJQ;SCHEMBL7151431;ZINC2526313;AKOS015909015;AM001310;4-AMINO-5-CYCLOHEXYL-3-HYDROXY-PENTANOICACID;I14-34063
Cyclohexylstatine is a chiral amino acid derivative featuring a cyclohexyl-substituted statine scaffold that presents a stereodefined carbon framework for tight control during synthetic elaboration. The molecule contains the amino acid functional motif (amino and carboxyl functionality, typically handled under protection or as an activated derivative) that enables conversion into peptide-compatible forms while preserving the stereochemistry of the statine center. The cyclohexyl side chain provides a hydrophobic, conformationally biasing element that can influence binding-site interactions in biochemical assays and can be exploited in peptidomimetic design. The amino acid reactivity profile supports standard amino acid chemistry, including N-protection for chemoselective coupling and carboxyl activation for amide bond formation, making it suitable as a research intermediate and chiral building block.
1. Peptide Synthesis
Cyclohexylstatine is applied in peptide synthesis and peptidomimetic construction as a statine-based amino acid building block for incorporation into inhibitor-like sequences. The amino acid backbone enables conversion to peptide-coupling-ready derivatives through N-protection and carboxyl activation strategies, supporting chemoselective formation of amide bonds under peptide coupling conditions. The stereogenic statine framework can be retained through protected-amino-acid handling, allowing stereodefined analogs to be generated for structure-activity relationship studies. Downstream, Cyclohexylstatine-containing peptides and peptide analogs can be used as reference compounds for assay development and as defined substrates in biochemical characterization.
2. Enzyme Inhibitor Design
Cyclohexylstatine is used in enzyme studies and inhibitor design workflows where statine-like amino acid motifs function as transition-state mimetic elements. The carboxyl and amino functionalities, when appropriately protected or incorporated into an amide context, can present binding-relevant geometry while the cyclohexyl side chain contributes hydrophobic contacts and conformational preference. The chiral center supports stereospecific binding hypotheses, enabling the synthesis of diastereomerically defined analog sets for mechanistic evaluation. Cyclohexylstatine-derived peptidomimetics can be prepared as biochemical research intermediates for inhibitor panels and for mapping structure-function relationships in enzyme active-site recognition.
3. Chiral Building Block Development
Cyclohexylstatine is suitable for chiral synthesis programs that require a stereodefined amino acid intermediate with a hydrophobic cyclohexyl substituent. The statine scaffold provides a platform for stereocontrolled derivatization, including N-protection for selective functional group manipulation and carboxyl activation for downstream coupling chemistry. The cyclohexyl side chain can be leveraged to tune lipophilicity and conformational behavior in synthetic libraries, supporting fragment-like incorporation into larger chiral molecules. Cyclohexylstatine can therefore serve as a chiral amino acid intermediate in fine chemical synthesis routes that target stereochemically defined peptidomimetics and related functional compounds.
4. Chemical Biology Probes
Cyclohexylstatine is applied in chemical biology research to generate amino-acid-based probes and labeled analogs for studying enzyme recognition and substrate processing. The amino acid functionality supports attachment to linkers through standard peptide coupling logic, while the statine stereocenter helps maintain binding-relevant three-dimensional features in probe constructs. N-protected forms can be used to manage chemoselective conjugation, and carboxyl-derived intermediates can be transformed into amide or other stable linkages for bioconjugation-compatible architectures. Cyclohexylstatine-containing probe molecules can be used as defined reagents for mechanistic studies, target engagement experiments, and analytical method development.
5. Pharmaceutical Intermediate Preparation
Cyclohexylstatine is relevant to pharmaceutical intermediate preparation and process chemistry development where stereodefined amino acid derivatives are manufactured as inputs for downstream active pharmaceutical ingredient synthesis. The protected amino acid chemistry associated with statine scaffolds supports scalable handling of amino and carboxyl functionalities, enabling conversion into activated intermediates for controlled amide formation in subsequent steps. The hydrophobic cyclohexyl side chain can influence crystallization behavior and solid-state handling, which are practical considerations in industrial route design. Cyclohexylstatine-derived intermediates can be employed to build defined peptidomimetic segments in synthesis planning, supporting consistent stereochemical outcomes for specialty chemical production.
6. Fine Chemical Synthesis
Cyclohexylstatine is utilized in fine chemical synthesis as a chiral, amino acid-derived scaffold for constructing complex nitrogen-containing intermediates and peptidomimetic fragments. The amino acid motif enables systematic protection-group strategies, including N-protection for selective transformations and carboxyl activation for coupling, while the stereogenic statine framework supports stereoretentive assembly of larger molecules. The cyclohexyl side chain provides a hydrophobic handle that can be carried through multi-step sequences and used to modulate physicochemical properties of final intermediates. Cyclohexylstatine can therefore function as a practical biochemical research intermediate and synthetic building block for generating structure-defined libraries, analytical standards, and downstream functional molecules in applied chemistry settings.
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