D-Lanthionine is a sulfur-containing, non-proteinogenic amino acid derivative in which two thioether-linked alanine units form the lanthionine scaffold, featuring a thioether bridge rather than a free thiol. The molecule contains both an amino group and a carboxyl group, with stereochemistry specified as the D-form at the alanine-derived stereocenters implied by the D designation. D-Lanthionine is used in peptide chemistry and structure-activity studies as a defined building block for incorporating lanthionine motifs and for preparing constrained thioether-containing peptide derivatives used in chemical biology and analytical method development.
CAT No: CP07803
D-Lanthionine is a sulfur-containing amino acid derivative characterized by a thioether-linked structure connecting two carbon centers, forming a rigid thioether bridge that distinguishes it from standard thioether-free amino acids. The molecule bears an amino functionality and a carboxylic acid (or acid/base forms depending on isolation), enabling salt formation and controlled reactivity in peptide coupling chemistry. Its stereochemical designation (D-) specifies the absolute configuration at the relevant chiral carbon, which can influence conformational preferences and stereospecific incorporation into peptide-like scaffolds. The thioether linkage provides distinct chemical stability relative to thiols while still enabling downstream transformations such as oxidation-state modulation and selective functionalization strategies in synthetic organic chemistry.
1. Peptide Synthesis
D-Lanthionine supports peptide building block preparation and thioether-bridged motif construction in peptide synthesis workflows where cystine-like or lanthionine-like connectivity is required. The amino and carboxyl groups enable standard peptide coupling chemistry after appropriate activation, while the thioether bridge constrains backbone geometry and can be used to stabilize folded conformations in peptide analogs. D-stereochemistry can be leveraged for stereodefined incorporation into lantibiotic-inspired structures or lanthionine-containing peptide mimetics, where stereochemical fidelity affects scaffold conformation. Downstream, D-Lanthionine can serve as a defined intermediate for generating thioether-containing peptide fragments and for assembling combinatorial libraries of constrained amino acid residues.
2. Peptidomimetics
D-Lanthionine is suitable for peptidomimetic and constrained scaffold design in medicinal chemistry research programs that require thioether-bridged rigidity without introducing disulfide exchange. The thioether linkage and chiral center together can be used to tune local stereochemistry, modulate hydrogen-bonding patterns via the amino and carboxyl functionalities, and influence conformational bias in structure-activity relationship studies. Incorporation into peptide-like backbones can enable systematic comparison of bridge geometry and stereochemical effects on binding-relevant conformations. Synthetic routes can apply amino acid derivatization and protection/deprotection planning to maintain selective coupling at the desired termini while preserving the thioether bridge for later functionalization.
3. Chemical Biology Labeling
D-Lanthionine can be employed in chemical biology research where sulfur-containing amino acid analogs are used to probe recognition, uptake, or processing of thioether-bearing motifs. The amino and carboxyl groups allow conversion into activated derivatives for conjugation strategies, while the thioether bridge provides a chemically stable handle relative to thiols under many oxidative conditions. D-stereochemical specification supports stereocontrolled incorporation into peptide conjugates or biomolecule-reactive intermediates that mimic lanthionine-like structural features. Resulting conjugates can function as analytical probes, affinity tags, or scaffold components for studying biomolecular interactions that depend on constrained sulfur-linked geometry.
4. Process Chemistry Intermediate
D-Lanthionine functions as a chiral amino acid intermediate for industrial fine chemical synthesis where sulfur-bridged amino acid motifs are required as feedstocks. The presence of both amino and carboxylic acid functionalities supports salt formation and controlled handling during manufacturing, while the thioether bridge provides stability that can simplify downstream processing compared with disulfide-containing analogs. D-stereochemistry enables stereospecific downstream synthesis of lanthionine-containing building blocks, peptide fragments, or protected amino acid derivatives used in multi-step production sequences. The compound's defined structure supports route design for scalable conversion into coupling-ready forms and into downstream thioether-containing specialty intermediates.
5. Analytical Standards
D-Lanthionine can serve as an analytical reference material for amino acid profiling and sulfur-containing residue identification in peptide and protein hydrolysate workflows. The amino acid backbone and thioether linkage provide characteristic chemical behavior that can be exploited for method development in chromatographic separation and mass-based detection of lanthionine-like residues. D-stereochemical identity supports stereospecific discrimination when analytical methods are designed to distinguish D- and L- configurations or to resolve thioether-bridged species. Downstream, D-Lanthionine-derived standards can be used to calibrate quantitation, validate derivatization steps, and support impurity mapping for thioether-containing peptide synthesis and related manufacturing analytics.
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