cinnamycin solid-phase peptide synthesis total chemical synthesis phase peptide synthesis - cica-peptide-shampoo chemical synthesis Cinnamycin Total Chemical Synthesis via Solid-Phase Peptide Synthesis

bioelements-power-peptide The dominant search intent for "cinnamycin solid-phase peptide synthesis total chemical synthesis" is to understand how cinnamycin, a specific lantibiotic, can be synthesized using solid-phase peptide synthesis (SPPS) and to explore the broader context of total chemical synthesis for such complex peptides. The results indicate a strong interest in the methodologies, challenges, and advancements in synthesizing lanthipeptides, with SPPS being a prominent technique.

Tier 1 Entities and Phrases:

* Core Topic: cinnamycin solid-phase peptide synthesis total chemical synthesis

* Key Entities: cinnamycin, lantibiotic, solid-phase peptide synthesis (SPPS), total chemical synthesis

* High-Relevance Phrases: solid-phase synthesis, solid-supported chemical synthesis, synthesis

Tier 2 Entities and Phrases:

* Related Concepts: peptide synthesis, chemical synthesis, lanthipeptides, post-translational modifications, amino acid derivatives, resin, reagents, protecting group, dehydro amino acids, thioethers, cyclized peptides, lysinoalanine (Lal) bridge, lan, MeLan

* Methodologies/Techniques: liquid-phase synthesis, in vivo, Fmoc-based SPPS, solution-phase peptide synthesis

* Attributes/Properties: 19 amino acid lantibiotic, unusual lysinoalanine bridge, prepeptides, mature form

Tier 3 Entities and Phrases:

* Repetitive mentions of "solid," "phase," "peptide," "synthesis" without specific context.

* General descriptions of peptide synthesis without direct connection to cinnamycin or SPPS challenges.

* Commercial product mentions (e.Synthesis Notesg.作者：A Ökesli·2011·被引用次数：147—... peptide of CinA (CinA1–19) was synthesized bysolid-phase peptide synthesis. As expected, His10-CinM showed no activity in the absence of the leader peptide ..., "Spectrum specializes in providing.It discusseshow solid phase peptide synthesis is performed, the amino acid derivatives, resin and reagents used in peptide synthesis, and some of the common ....Synthesis Notes.")Solid Phase Peptide Synthesis.

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The total chemical synthesis of complex natural products like cinnamycin, a 19-amino acid lantibiotic, presents significant challenges and opportunities in the field of peptide chemistry. Specifically, achieving the total synthesis of cinnamycin through solid-phase peptide synthesis (SPPS) requires mastering intricate methodologies to replicate its unique structure, including modified amino acids and thioether cross-links. SPPS has emerged as a cornerstone technique for assembling peptides step-by-step on a solid support, a process that has been instrumental in the synthesis of various lanthipeptides and their analogues.

Cinnamycin is characterized by its unusual post-translational modifications, notably the presence of lanthionine (Lan) and methyllanthionine (MeLan) residues, along with a lysinoalanine (Lal) bridge. These structural features are critical to its biological activity and pose considerable hurdles for chemical synthesis. While biosynthesis produces these modifications naturally, total chemical synthesis aims to replicate the mature peptide from its constituent amino acids using chemical means, often employing solid-supported chemical synthesis approaches to facilitate purification and reaction efficiency.Nine Post-translational Modifications during the ...

The Role of Solid-Phase Peptide Synthesis (SPPS)

Solid-phase peptide synthesis, or SPPS, revolutionized peptide chemistry by anchoring the growing peptide chain to an insoluble resinPeptides are chemically synthesizedby the condensation reaction of the carboxyl group of one amino acid to the amino group of another. Protecting group .... This strategy simplifies the process by allowing excess reagents and byproducts to be washed away easily after each coupling step, a significant advantage over traditional solution-phase peptide synthesis, which often requires laborious purification steps such as recrystallization or column chromatography.

The fundamental process of SPPS involves sequentially adding protected amino acids to the N-terminus of a growing peptide chainThe role of chemical synthesis in developing RiPP antibiotics. Key components include:

* Resin Support: An insoluble polymer matrix to which the C-terminal amino acid is attached.Thetotal synthesisof nisin'^^ has not been optimised for thesolid phase, although there have been reports of thesynthesisof smaller lanthionine ...

* Protected Amino Acids: Amino acids with temporary protecting groups on their reactive side chains and alpha-amino groups to prevent unwanted reactionsOrthogonally Protected Lanthionines: Synthesis and Use .... Common protecting group strategies, such as Fmoc (9-fluorenylmethyloxycarbonyl), are employed.

* Coupling Reagents: Chemicals that facilitate the formation of peptide bonds between the activated carboxyl group of one amino acid and the free amino group of the peptide chain attached to the resinPeptidesplay a central role in numerous biological and physiological processes. They also may be critical for research endeavors in the post-genomic and ....

* Deprotection Reagents: Chemicals used to remove the temporary protecting groups, typically the alpha-amino protecting group, to prepare for the next amino acid addition.作者：A Ökesli·2011·被引用次数：147—Cinnamycin is a 19 amino acid lantibioticthat contains one Lan and two MeLan. Cinnamycin also contains an unusual lysinoalanine (Lal) bridge.

For complex peptides like cinnamycin, SPPS is often adapted to incorporate non-proteinogenic amino acids and to form internal cross-links. The synthesis of lanthionine-containing peptides, for instance, requires specialized building blocks and reaction conditions to cyclize dehydro amino acids and thioethers within the peptide backboneRecent advances in synthetic analogues of lantibiotics.

Challenges in Total Chemical Synthesis of Lanthipeptides

The total chemical synthesis of lantibiotics, including cinnamycin, is inherently more complex than that of linear peptides. The presence of thioether cross-links, formed from dehydration of serine or threonine residues followed by cyclization with cysteine residues, creates intricate three-dimensional structures.作者：EL Ongey·2016·被引用次数：137—Industrial peptide production is commonly based on three alternative technologies includingsolid-phase synthesis, liquid-phase synthesis, and in vivo ... These modifications are crucial for the peptide's stability, conformation, and bioactivity.

Key challenges in the total synthesis of cinnamycin via SPPS include:

* Formation of Thioether Bridges: Synthesizing the lanthionine and methyllanthionine residues requires specific chemical steps to achieve dehydration and cyclization. This often involves specialized reagents and carefully controlled reaction conditions to ensure regioselectivity and stereoselectivity2012年8月1日—Solid-supportedchemical synthesisenabled thetotal synthesisof the lantibiotic lacticin 481 and analogues containing cross-links with ....

* Incorporation of Modified Amino Acids: The synthesis protocols must accommodate the use of protected dehydro amino acids and other modified building blocks that are not standard in ribosomal protein synthesis.

* Lysinoalanine Bridge Formation: The unusual lysinoalanine bridge, formed from a lysine and an alanine residue, adds another layer of complexity, requiring specific coupling strategies or post-synthetic modifications.

* Scalability and Yield: Achieving high yields and purity in the total chemical synthesis of such a complex peptide can be difficult, especially when scaling up for larger quantities.作者：A Ökesli·2011·被引用次数：147—Cinnamycin is a 19 amino acid lantibioticthat contains one Lan and two MeLan. Cinnamycin also contains an unusual lysinoalanine (Lal) bridge.

* Protecting Group Strategies: Orthogonal protecting group strategies are essential to selectively deprotect specific functional groups without affecting others, particularly when constructing complex cross-linked structures.作者：EL Ongey·2016·被引用次数：137—Industrial peptide production is commonly based on three alternative technologies includingsolid-phase synthesis, liquid-phase synthesis, and in vivo ...

Despite these challenges, advances in peptide synthesis methodologies, including optimized SPPS protocols, novel coupling reagents, and innovative protecting group chemistries, continue to push the boundaries of what is achievable in the total chemical synthesis of complex natural products like cinnamycin. These efforts are vital for producing sufficient quantities for biological studies, developing analogues with improved therapeutic properties, and gaining deeper insights into the structure-activity relationships of these potent antimicrobial peptides.