solid phase synthesis of lanthionine-containing peptides with - solid-phase-peptide-synthesis-protocol containing

solid-phase-peptide-synthesis-mechanism The solid phase synthesis of lanthionine-containing peptides represents a critical advancement in the creation of complex biomolecules with unique structural and functional properties.An Analogue of Rings D and E of the Lantibiotic Nisin Lanthionine, a non-proteinogenic amino acid characterized by a thioether bond between a cysteine and a serine or threonine residue, is a hallmark of lantibiotics and other bioactive peptides作者：EL Ongey·2016·被引用次数：138—These achievements opened exciting opportunities forsolid-phase peptide synthesis (SPPS) of lanthipeptides(Fig. 4a2), since it was now possible to create .... The development of robust solid-phase peptide synthesis (SPPS) strategies has made it more feasible to construct these challenging peptide architectures, enabling their study and potential therapeutic applications.

Advancements in Solid-Phase Lanthionine Peptide Synthesis

The field has seen significant progress in developing methods for the total solid phase synthesis of lantibiotics and their analogues.Orthogonally Protected Lanthionines: Synthesis and Use for ... Early work focused on creating orthogonally protected lanthionine building blocks, such as those with Boc, Fmoc, and allyl methyl protecting groups, which are suitable for combinatorial and solid-phase peptide chemistry. These protected lanthionines allow for controlled incorporation into growing peptide chains on a solid support.作者：Y Fu·2023·被引用次数：15—SUMMARY. Lanthipeptide biosynthetic genes are present in a wide range of bacteria, providing convenient tools for engineering bioactive lan-.

More sophisticated approaches have emerged, including one-pot, high-yield procedures that rely on the S-alkylation of cysteine residues with serine or threonine precursors.Lanthionines for solid phase synthesis This strategy streamlines the synthesis of lanthionine-containing peptides and has been applied to constructing overlapping lanthionine bridges, a common feature in many natural lantibiotics like nisin.作者：EL Ongey·2016·被引用次数：138—These achievements opened exciting opportunities forsolid-phase peptide synthesis (SPPS) of lanthipeptides(Fig. 4a2), since it was now possible to create ...

Key Methodologies and Protecting Group Strategies

A crucial aspect of successful solid-phase lanthionine peptide synthesis is the implementation of appropriate protecting group strategies. Orthogonal protecting groups are essential to ensure that the lanthionine thioether bond can be formed selectively without interfering with other peptide functionalities or the solid support.

* Fmoc/tBu Chemistry: This widely used SPPS strategy has been adapted for the synthesis of peptides containing lanthionine, including derivatives like L,L-lanthionine sulfoxide. The Fmoc group on the N-terminus allows for facile deprotection under basic conditions, while acid-labile tBu-based protecting groups are used for side chainsA methodology for thesolid-phase synthesis of the overlapping lanthionine bridgesfound in many lantibiotics has been developed and selected deprotection ....

* Orthogonal Protection: The development of orthogonally protected lanthionines has been pivotalSynthesis of Lanthionine‐Containing Peptides on Solid‐Phasevia an Orthogonal Protecting Group Strategy ... Mohd Mustapa, M. F.; Tabor, A. B.; Chubb, N. A. L.; .... This allows for the selective formation of the thioether bond on-resin, often through S-alkylation, while maintaining the integrity of other amino acid side chains and the peptide linkage to the solid supportUS6897289B1 - Peptide synthesis procedure in solid phase. For example, strategies for synthesizing analogues of nisin fragments have utilized this approach.

* Late-Stage Cyclization: Some methods employ late-stage cyclization strategies after the initial peptide chain assembly. This can involve forming disulfide or thioether bonds towards the end of the synthesis, either on-resin or after cleavage from the solid support.

Applications and Future Directions

The ability to synthesize lanthionine-containing peptides on solid phase has opened avenues for developing novel therapeutic agentsArticle. Lanthipeptides, including lantibiotics, exhibit a range of biological activities, such as antimicrobial, anticancer, and immunomodulatory effects. Synthetically produced analogues allow for structure-activity relationship studies and the optimization of these properties作者：SN Mthembu·2022·被引用次数：12—Lanthionine Peptides by S-Alkylationwith · Substituted Cyclic Sulfamidates Promoted by Activated Molecular · Sieves: Effects of the Sulfamidate ....

The solid-phase peptide synthesis (SPPS) of lanthipeptides is a continuously evolving field. Research continues to focus on developing more efficient, greener, and versatile methodsThe aim of this project is to develop the foundation of thetotal solid phase synthesis of lantibioticsand their analogues by investigating the possibility .... This includes exploring new coupling reagents, expanding the range of applicable protecting groups, and improving the synthesis of challenging peptide sequences with multiple thioether bridges.作者：K Manzor·2017·被引用次数：9—...containingreplacements for the Dha at position 5, have been successfully prepared bysolid-phase peptide synthesis. The Dha replacements ... The ultimate goal is to provide chemists with reliable tools to access a diverse library of lanthionine-containing peptides for various research and biotechnological applications.