peptide-since The dominant search intent for "oxa-lanthionine synthesis peptide" is to understand the methods and challenges involved in creating peptides that contain oxa-lanthionine structures, often in the context of lantibiotics or their analogues.作者：R Dickman·2019·被引用次数：51—28 We have developed a powerful solid-phasepeptide synthesis(SPPS) strategy for thesynthesisoflanthionine- containingpeptides.29 This is ...
Tier 1 Entities & Phrases:
* oxa-lanthionine synthesis peptide
* oxa-lanthionine
* lanthionine
* peptide synthesis
* synthesis
* lanthipeptides
* oxa
* total synthesis
Tier 2 Entities & Phrases:
* Lanthionine
* peptides
* synthesized oxa
* Oxa-DAP
* synthesized in five steps
* synthesizing lanthionine-containing peptides
* ribosomally synthesized, polycyclic natural peptide products
* Synthesis of oxa-lanthionine
* ribosomally-synthesized antimicrobial peptides
* ribosomally synthesized and posttranslationally modified peptides
* lanthipeptide synthesis
* Oxa-Lacticin A2
* lanthionine peptide
* solid-phase peptide synthesis (SPPS)
* orthogonally protected
Tier 3 Entities & Phrases:
* Oxa-lanthionine is a thioether analogue of cystine
* Oxa-DAP is a substrate of DAP epimerase
* Oxa-Lacticin A2 retains independent antimicrobial activity against Gram-positive bacteria but lacks the synergistic
The synthesis of oxa-lanthionine peptides represents a specialized area within peptide chemistry, focusing on the creation of complex peptide structures that feature oxa-lanthionine residues. Lanthionine, a thioether analogue of cystine, is a characteristic component of lantibiotics, a class of ribosomally synthesized, post-translationally modified antimicrobial peptides. The incorporation of oxa-lanthionine, where the sulfur atom of the lanthionine bridge is replaced by oxygen, introduces unique structural and chemical properties, making its synthesis a significant challenge and an active area of research. Developing effective strategies for the total synthesis of these modified peptides is crucial for understanding their biological functions and for potential therapeutic applications.
Lanthionine peptides, often referred to as lanthipeptides, are distinguished by the presence of multiple thioether cross-links formed between cysteine residues. These cross-links are key to their three-dimensional structure and biological activityA Structural View on the Maturation of Lanthipeptides. Oxa-lanthionine is a structural variant where the lanthionine linkage is modified, typically involving an oxygen atom bridging two amino acid residues instead of sulfur.作者：M Lagedroste·2020·被引用次数：47—Lanthipeptides areribosomally synthesized and posttranslationally modified peptides, which display diverse bioactivities (e.g., antifungal, antimicrobial, and ... This modification can significantly alter the peptide's stability, conformation, and interaction with biological targets.
Lanthipeptides themselves are a diverse group of natural products with potent antimicrobial activities. They are ribosomally synthesized as precursor peptides, which then undergo extensive post-translational modifications, including dehydration of serine and threonine residues and cyclization to form lanthionine or oxa-lanthionine bridges. Examples like nisin and lacticin 3147 highlight the importance of these modified peptides.University of Alberta Research into their synthesis aims to replicate these natural structures and to create novel analogues with improved or altered properties.
The synthesis of oxa-lanthionine-containing peptides presents several hurdles that distinguish it from standard peptide synthesis.作者：EL Ongey·2016·被引用次数：138—Lanthipeptides areribosomally synthesized, polycyclic natural peptide productsthat are usually characterized by the presence of the thioether cross-linked ... Traditional solid-phase peptide synthesis (SPPS) methods need significant adaptation. Key challenges include:
* Stereoselective Formation of Oxa-Lanthionine Bridges: Creating the oxa-lanthionine linkage with the correct stereochemistry is critical.作者：J Deng·2020—The precusorpeptidewill be dehydrated and cyclized by the modification enzymes to form thelanthioninerings. Subsequently, the modified prenisin is ... This often requires specific reagents and carefully controlled reaction conditions to ensure the desired ring structure is formed efficiently and without epimerization.
* Orthogonal Protection Strategies: To build complex peptides, amino acid side chains and terminal groups must be protected during synthesis. For oxa-lanthionine formation, orthogonal protection schemes are essential, allowing for selective deprotection and subsequent cyclization steps without affecting other parts of the peptide chain.
* Peptide Backbone Stability: The modified residues and cross-links can influence the overall stability of the peptide backbone, particularly during cleavage from the solid support or during subsequent chemical manipulations.
* Incorporation into Complex Sequences: Integrating the oxa-lanthionine moiety into longer peptide sequences, especially those mimicking natural lantibiotics, requires careful planning of the synthetic route, often involving fragment condensation strategies.
Researchers have explored various synthetic methodologies to overcome these challenges. One common approach involves building the oxa-lanthionine precursor and then incorporating it into a peptide chain.作者：H Liu·2007·被引用次数：80—Oxa-DAP is a substrate of DAP epimerase, a key enzyme for biosynthesis of l-lysine and formation of peptidoglycan precursors. Orthogonally protected analogues ... This can be achieved through:
* De Novo Synthesis of Oxa-Lanthionine Residues: Developing synthetic routes for the oxa-lanthionine building block itself, often starting from simpler amino acid derivatives. These routes frequently involve aziridine ring opening with appropriate nucleophiles or other cyclization strategies.
* Solid-Phase Peptide Synthesis (SPPS) Strategies: Adapting SPPS for the synthesis of lanthionine-containing peptides, including oxa-lanthionine variants. This often involves using specially protected amino acids and optimizing coupling and deprotection steps.作者：A Bakhtiary·2017·被引用次数：70—17d Our group has previouslysynthesized oxa- and desmethyl-lanthionineanalogues of LtnA2 (oxa-. LtnA2 (7) and desMe-LtnA2 (8)), whereinlanthioninesulfurs ... Some methods focus on late-stage synthesis, where the oxa-lanthionine formation occurs towards the end of the peptide assembly.
* Fragment Condensation: For larger peptides like nisin, a fragment condensation approach is often employed. This involves synthesizing smaller peptide segments, each potentially containing an oxa-lanthionine residue or its precursor, and then joining these fragments together to form the complete peptide. This strategy can simplify the overall synthesis and improve yields.Synthesisand Biological Activity ofOxa-Lacticin A2, a Lantibiotic Analogue with Sulfur Replaced by Oxygen ...SynthesisofPeptidesContaining Overlapping ...
The ability to synthesize oxa-lanthionine peptides has significant implications. It allows for the detailed study of lantibiotics, including their mechanisms of action and structure-activity relationships. For instance, analogues like oxa-lacticin A2, where sulfur is replaced by oxygen, have been synthesized to probe the role of the thioether bridge in biological activity.
Beyond fundamental research, the synthesis of these peptides opens avenues for developing novel antimicrobial agents. The increasing threat of antibiotic resistance necessitates the exploration of new therapeutic scaffolds, and modified peptides like oxa-lanthionine-containing structures offer promising candidates. Future research will likely focus on developing more efficient and scalable synthetic methods, exploring a wider range of oxa-lanthionine modifications, and engineering peptides with enhanced potency and specificity.作者：R Dickman·2018—This thesis describes thesynthesisand structural analysis of the target-binding region of nisin and its close structural relative mutacin I. The lantibiotics ... The integration of chemical synthesis with biotechnological approaches may also offer new pathways for producing these complex molecules.
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