Super silyl-based stable protecting groups for both the C- and N-terminals of peptides: applied as effective hydrophobic tags in liquid-phase peptide synthesis

An, Wei; Yamamoto, Hisashi

doi:10.1039/d3sc01239e

Cited by 3 publications

References 79 publications

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Improved Electrochemical Peptide Synthesis Enabled by Electron‐Rich Triaryl Phosphines

Shinjo‐Nagahara,

Okada,

Hiratsuka

et al. 2024

Chemistry A European J

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While remarkable progress has been made in the development of peptide medicines, many problems related to peptide synthesis remain unresolved. Previously, we reported electrochemical peptide synthesis using a phosphine as a potentially recyclable coupling reagent. However, there was room for improvement from the point of view of reaction efficiency, especially in the carboxylic acid activation step and the peptide bond formation step. To overcome these challenges, we searched for the optimal phosphine. Among phosphines with various electronic properties, we found that electron‐rich triaryl phosphines improved the reaction efficiency. Consequently, we successfully performed electrochemical peptide synthesis on sterically hindered and valuable amino acids. We also synthesized oligopeptides that were challenging with our previous method. Finally, we examined the effect of substituents on the phosphine cations, and gained some insights into reactivity, which will aid researchers designing reactions involving phosphine cations.

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Improved Electrochemical Peptide Synthesis Enabled by Electron‐Rich Triaryl Phosphines

Shinjo‐Nagahara,

Okada,

Hiratsuka

et al. 2024

Chemistry A European J

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Scalable preparation of green C-terminal amidation peptide-synthesis TAGs and the optimized TAG-assisted liquid-phase synthesis of eptifibatide

Li,

Wang,

Zhang

et al. 2024

Sustainable Chemistry and Pharmacy

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Third Wave for Peptide Synthesis: Liquid-phase Peptide Synthesis (LPPS)

Sharma,

Kumar,

de la Torre

et al. 2024

Sustainability in Tides Chemistry

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Liquid-phase peptide synthesis (LPPS) is considered as the third wave for peptide synthesis, and combines the advantages of classical solution peptide synthesis (CSPS) and solid-phase peptide synthesis (SPPS). In LPPS, the peptide is loaded on a soluble support and elongation is carried out in solution, thereby rendering characteristic properties. LPPS protocols align well with the 12 principles of green chemistry, which allows the large-scale production of peptides and reduces the use of excess reagents and solvents. In this chapter, tags associated with LPPS for industrial-scale peptide synthesis are discussed under the following categories: membrane-enhanced peptide synthesis (MEPS), group-assisted purification (GAP), PolyCarbon, silicon-based tags, and miscellaneous.

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Super silyl-based stable protecting groups for both the C- and N-terminals of peptides: applied as effective hydrophobic tags in liquid-phase peptide synthesis

Abstract: Tag-assisted liquid-phase peptide synthesis (LPPS) is one of the important processes in peptide synthesis in pharmaceutical discovery. Simple silyl groups have positive effects when incorporated in the tags due to...

Cited by 3 publications

References 79 publications

Improved Electrochemical Peptide Synthesis Enabled by Electron‐Rich Triaryl Phosphines

Improved Electrochemical Peptide Synthesis Enabled by Electron‐Rich Triaryl Phosphines

Scalable preparation of green C-terminal amidation peptide-synthesis TAGs and the optimized TAG-assisted liquid-phase synthesis of eptifibatide

Third Wave for Peptide Synthesis: Liquid-phase Peptide Synthesis (LPPS)

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