Multi-site esterification: a tunable, reversible strategy to tailor therapeutic peptides for delivery

Bannon, Mark S.; Ellena, Jeffrey F.; Gourishankar, Aditi S.; Marsh, Spencer R.; Trevisan-Silva, Dilza; Sherman, Nicholas E.; Jourdan, L. Jane; Gourdie, Robert G.; Letteri, Rachel A.

doi:10.1039/d4me00072b

Mol. Syst. Des. Eng.

2024

DOI: 10.1039/d4me00072b

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Multi-site esterification: a tunable, reversible strategy to tailor therapeutic peptides for delivery

Mark S. Bannon,

Jeffrey F. Ellena,

Aditi S. Gourishankar

et al.

Abstract: Peptides are naturally potent and selective therapeutics with massive potential; however, low cell membrane permeability limits their clinical implementation, particularly for hydrophilic, anionic peptides with intracellular targets.

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Fischer-Speier Esterification and Beyond: Recent Mechanicistic Advances

Mannu,

Mele

2024

Catalysts

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Over the past 130 years, Fischer-Speier esterification has been established as the benchmark method for synthesizing esters from organic acids and alcohols. The reaction’s versatility, arising from the vast combinations of starting materials and the numerous catalytic alternatives to the traditional H2SO4, has maintained its relevance, with a steady flow of publications addressing new developments. This review highlights the most significant contributions to Fischer-Speier esterification over the past five years, with a particular emphasis on mechanistic advancements and innovative catalytic systems. Both homogeneous and heterogeneous catalytic approaches are discussed, including novel catalysts leveraging hydrogen-bonding interactions and systems offering fresh insights into specific reaction mechanisms and atypical methodologies. Some of these catalytic systems, as ionic liquids or sulfonated heterogeneous catalytic precursors, reached excellent yields (>90%), e.g., in the synthesis of fatty acids methyl esters. Also, classic catalysts such as H2SO4 and para-toluen sulfonic acid were optimized for quantitative conversions (e.g., in the esterification of trans-cinnamic acid with methanol). A consistent number of catalysts was studied with model substrates (as benzoic acid in combination with methanol, ethanol, and ethylene glycol), and new activation pathways were presented.

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Fischer-Speier Esterification and Beyond: Recent Mechanicistic Advances

Mannu,

Mele

2024

Catalysts

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show abstract

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Multi-site esterification: a tunable, reversible strategy to tailor therapeutic peptides for delivery

Abstract: Peptides are naturally potent and selective therapeutics with massive potential; however, low cell membrane permeability limits their clinical implementation, particularly for hydrophilic, anionic peptides with intracellular targets.

Cited by 1 publication

References 60 publications

Fischer-Speier Esterification and Beyond: Recent Mechanicistic Advances

Fischer-Speier Esterification and Beyond: Recent Mechanicistic Advances

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