L-trans-Epoxysuccinyl-Leu-4-guanidinobutylamide is a protected, modified amino acid derivative featuring a leucine-derived backbone bearing an epoxysuccinyl moiety and a 4-guanidinobutylamide side chain, placing it in the class of amino acid amide conjugates used in structure-activity and enzyme-substrate related studies. The molecule contains an amide linkage at the terminal carboxyl-derived position and an epoxide-containing epoxysuccinyl functionality along with a guanidine group that provides strong basicity and hydrogen-bonding capacity, while the "L-" and "trans" descriptors specify the indicated stereochemical relationships in the chiral framework. As a chemically defined building block, it is employed in peptide chemistry and chemical biology workflows that require a leucine-like scaffold with a reactive epoxide and a guanidinium functional handle for preparing defined substrates, analogues, and analytical standards.
CAT No: CP27346
CAS No:66701-25-5
Synonyms/Alias:E-64;L-trans-Epoxysuccinyl-Leu-agmatine
L-trans-Epoxysuccinyl-Leu-4-guanidinobutylamide is a chiral, amino acid-derived peptidomimetic amide in which an L-leucine framework is tethered to a trans-epoxysuccinyl motif and a 4-guanidinobutyl side chain. The molecule contains an epoxide electrophile, a guanidine functionality capable of strong hydrogen bonding and salt formation, and an amide linkage that supports defined conformational and polarity profiles in protein and enzyme binding studies. The stereochemical relationship between the epoxide-bearing carbon centers and the L-leucine stereocenter is critical for reproducible reactivity and for maintaining consistent geometry during peptide-like scaffold construction. The combination of an electrophilic epoxide and a basic guanidine makes the compound suitable as a reactive biochemical research intermediate and as a downstream precursor for further functional group transformation.
1. Enzyme Inhibitor Studies
L-trans-Epoxysuccinyl-Leu-4-guanidinobutylamide is applied in enzyme mechanism research where epoxide electrophiles can participate in covalent or semi-covalent interactions with nucleophilic residues under controlled synthetic conditions. The trans-epoxysuccinyl group provides a defined stereochemical electrophilic handle, while the leucine-derived backbone and 4-guanidinobutyl side chain can support recognition through hydrophobic contacts and strong electrostatic/hydrogen-bonding interactions typical of enzyme active-site environments. The amide linkage maintains peptide-like polarity and can be incorporated into structure-activity relationship studies alongside related analogs. The resulting derivatives and analog panels can be used to map binding determinants and to generate mechanistic probes for biochemical assays and target validation workflows.
2. Peptidomimetic Scaffold Design
L-trans-Epoxysuccinyl-Leu-4-guanidinobutylamide is suitable for peptidomimetic construction in medicinal chemistry and chemical biology, where a leucine-based stereocenter and a guanidine-bearing side chain emulate key features of natural amino acid recognition. The epoxysuccinyl motif functions as a chemically addressable electrophile that can be retained for covalent probe design or transformed into alternative functional groups for non-covalent analogs. The presence of a stable amide and a basic guanidine enables controlled solubility behavior and facilitates subsequent derivatization steps such as salt formation, linker installation, or conversion of reactive intermediates into more stable analogs. Downstream scaffold generation can support fragment-to-lead refinement and SAR studies focused on side-chain placement, stereochemical constraints, and electrophile positioning.
3. Bioconjugation Chemistry
L-trans-Epoxysuccinyl-Leu-4-guanidinobutylamide can be employed in bioconjugation strategies where the epoxide electrophile enables targeted coupling to nucleophiles on biomolecules or affinity reagents. The guanidine functionality supports binding to negatively charged surfaces and can influence conjugate localization when used in labeling or pull-down workflows, while the leucine-derived amide provides a peptide-like anchor that can improve compatibility with proteinaceous targets. The trans-epoxysuccinyl stereochemistry can affect coupling outcomes and reproducibility of conjugate composition, particularly when comparing stereoisomeric or epoxide-regioisomeric analogs. The compound can serve as a reactive intermediate for generating labeled probes, affinity handles, or immobilized reagents that feed into downstream analytical research and biomolecule modification programs.
4. Protected Intermediate Synthesis
L-trans-Epoxysuccinyl-Leu-4-guanidinobutylamide is utilized as a chiral amino acid-derived intermediate for synthetic organic chemistry routes that require a preorganized L-leucine stereochemical element combined with a functionalized side chain. The amide and guanidine groups can be leveraged for orthogonal protection/deprotection planning during multistep synthesis, enabling selective transformations while maintaining the reactive epoxide-bearing motif for later-stage conversion. The electrophilic epoxysuccinyl segment can be selectively quenched or transformed to install alternative nucleophile-reactive or stable substituents, supporting the preparation of related protected amino acid derivatives and peptidomimetic building blocks. The resulting intermediates can be advanced into fine chemical synthesis programs where stereodefined amino acid chemistry and functional group interconversion are required for library production.
5. Process Chemistry Intermediate
L-trans-Epoxysuccinyl-Leu-4-guanidinobutylamide is relevant to process chemistry intermediate development for specialty chemical production, particularly where a defined stereochemical epoxide and a strongly basic guanidine must be carried through controlled manufacturing steps. The molecule's amide linkage provides a robust functional group handle for maintaining structural integrity across synthetic operations, while the trans-epoxysuccinyl motif enables planned downstream conversion into alternative electrophiles or stable derivatives used in subsequent synthesis. Guanidine can be managed through salt-state control and selective functionalization logic, supporting reproducible handling and consistent reactivity profiles during scale-up. The compound can therefore function as a stereodefined building block for producing families of amino acid-derived reagents and peptidomimetic intermediates used in industrial research supply chains and chemical manufacturing workflows.
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