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Oxa-lanthionine Solid-Phase Peptide Synthesis: A Detailed Exploration

The intricate field of peptide synthesis has seen remarkable advancements, particularly with the advent of solid-phase peptide synthesis (SPPS)作者：JM Palomo·2014·被引用次数：474—This review article highlights the strategies to successfully perform an efficientsolid-phase synthesisof complexpeptides.. Within this domain, the construction of peptides incorporating unusual amino acids, such as those featuring lanthionine cross-links, presents unique challenges and opportunities. This article delves into the methodologies and considerations surrounding oxa-lanthionine solid-phase peptide synthesis, highlighting its significance in the creation of complex and biologically relevant molecules.The enzymes Csd6 and Pgp2 are peptidoglycan (PG) proteases found in the pathogenic bacteria Helicobacter pylori and Campylobacter jejuni, respectively.

Understanding Oxa-lanthionine

Lanthionine is a thioether amino acid formed by the alkylation of a cysteine residue with an α,β-unsaturated amino acid. Its oxa counterpart, oxalanthionine, replaces the sulfur atom in the thioether linkage with an oxygen atom, creating an ether linkage. This structural modification, first explored by researchers like Vederas, offers a stable alternative to the lanthionine thioether, influencing the peptide's overall conformation and stability. The synthesis of orthogonally protected oxalanthionine derivatives is crucial for their successful integration into peptide chains during synthesis.

The Role of Solid-Phase Peptide Synthesis (SPPS)

Solid-phase peptide synthesis (SPPS), a cornerstone technique pioneered by R. Bruce Merrifield (for which he received the 1984 Nobel Prize in Chemistry), revolutionised peptide chemistry.Resins for Solid Phase Peptide Synthesis - Core Resins - AAPPTEC This method involves anchoring the C-terminal amino acid to an insoluble polymeric support (resin) and sequentially adding amino acids to the growing peptide chain. The solid support facilitates easy purification by simple washing steps, significantly streamlining the synthesis process. This approach is versatile and applicable to the total solid phase synthesis of various peptides, including those with complex modifications.作者：AJ Apostolos·2021·被引用次数：11—Here, we described a strategy that usessolid-phase peptide synthesisto construct a selenolanthionine m-DAP mimic. This probe was tolerated ...

Integrating Oxa-lanthionine into SPPS

The synthesis of lanthionine-containing peptides and their analogues, like those with oxalanthionine residues, often relies on SPPS strategies. Researchers have developed methods for synthesizing lanthionine-containing peptides by incorporating pre-formed, orthogonally protected lanthionine or oxalanthionine building blocks.Metabolic Processing of Selenium-based Bioisostere of ... This approach ensures regioselective formation of the desired cross-links.

Key considerations in this process include:

* Orthogonal Protection: The protecting groups on the amino and carboxyl termini of amino acids, as well as on the side chains, must be selectively removable under different conditions. This orthogonality is vital for controlled chain elongation and the formation of specific cross-links like lanthionine or oxa-lanthionine. For instance, methods for methods of solid-phase and solution phase peptide synthesis often emphasize the importance of careful protecting group strategies.Synthesis and Conformational Studies of the Lipid II- ...

* Resin Choice and Linker Chemistry: The selection of the appropriate resin and linker is critical for SPPS.Solid phase peptide synthesisis a known process in which amino acid residues are added to peptides that have been immobilized on a solid support. New amino ... The linker must be stable throughout the synthesis but also cleavable under mild conditions at the end to release the synthesized peptide作者：S Bregant·2005·被引用次数：101—We then used this orthogonally protectedlanthioninein thesolid-phase synthesisof an analogue of a fragment of nisin containing its ring C. The .... Various resins, such as for Solid Phase Peptide Synthesis, are available, each with specific properties.

* Coupling Reagents: Efficient coupling of activated amino acids to the solid-supported peptide chain is paramount. A wide array of coupling reagents are available to facilitate this process, ensuring minimal racemization and high yieldsSolid phase peptide synthesisis a known process in which amino acid residues are added to peptides that have been immobilized on a solid support. New amino ....

* Lanthionine/Oxa-lanthionine Formation: The specific step where the lanthionine or oxalanthionine ring is formed depends on the strategy作者：G Dirscherl·2009—peptidefMLF (N-formyl-L-methionine-L-leucine-L-phenylalanine), a targeting ...oxa-13 azabicyclo-. [10.2.1]pentadeca-1(14),6,12(15)-triene-14 .... This can occur either by incorporating a pre-synthesized modified amino acid or by forming the cross-link *in situ* after incorporating suitable precursor amino acids. For example, strategies for the solid-phase synthesis of a lanthionine sulfoxide- containing peptide involve specific chemical modifications during the SPPS process.

Applications and Significance

The ability to synthesize peptides containing oxa-lanthionine and other non-canonical amino acids opens doors to the creation of novel peptide therapeutics, diagnostics, and research tools.作者：S Mitchell·2018—...peptidehas also been synthesised using protectedoxa-lanthionines ...Synthesisof theLantibiotic. Lactocin S UsingPeptideCyclizations onSolid Phase. These modified peptides often exhibit enhanced stability against enzymatic degradation, improved bioavailability, and altered pharmacological profiles compared to their natural counterparts→stepwisesolid-phase synthesisof peptaibols, T.P. c 301. →stereoselectivesynthesisof a-amino acid andpeptidederivatives by the U-4CR of 2-acet-..

Lantibiotics, a class of ribosomally synthesized peptides that contain lanthionine and other thioether or ether cross-links, are a prime example of the biological significance of these structures. The chemical synthesis of these complex molecules, including fragments containing lanthionine, is an active area of research, often employing SPPS作者：JM Palomo·2014·被引用次数：474—This review article highlights the strategies to successfully perform an efficientsolid-phase synthesisof complexpeptides.. Automated solid-phase peptide synthesis further accelerates the production of these complex peptides for large-scale studies and potential therapeutic applicationsThe invention relates tomethods of solid-phase and solution phase peptide synthesisfor preparing peptide hydrazides useful in as intermediates in ....

The field of peptide science continues to evolve, with ongoing efforts to refine SPPS methodologies and expand the repertoire of accessible unnatural amino acids. The synthesis of peptides with unique structural features, such as those incorporating oxa-lanthionine, is a testament to the power and versatility of modern chemical synthesis.The World - of Peptides - Springer Link This allows for precise control over peptide structure, leading to a deeper understanding of structure-activity relationships and the design of novel biomoleculesAutomated solid-phase peptide synthesis to obtain .... The ongoing research into Solid Phase Peptide Synthesis underscores its continued importance in delivering complex peptides with high fidelityThe synthesis of the tripeptide substrate 6 via orthogonally ....