Lipidation of Peptides and Proteins

Görmer, Kristina; Waldmann, Herbert; Brunsveld, Luc

doi:10.1016/b978-008045382-8.00688-2

Cited by 3 publications

References 260 publications

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Late‐Stage Hydrocarbon Conjugation and Cyclisation in Synthetic Peptides and Proteins

2021

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The conventional S-alkylation of cysteine relies upon using activated electrophiles. Here we demonstrate high-yielding and selective S-alkylation and S-lipidation of cysteines in unprotected synthetic peptides and proteins by using weak electrophiles and a Zn 2 + promoter. Linear or branched iodoalkanes can S-alkylate cysteine in an unprotected 38-residue Myc peptide fragment and in a 91-residue miniprotein Omomyc, thus highlighting selective late-stage synthetic modifications.Metal-assisted cysteine alkylation is also effective for incorporating dehydroalanine into unprotected peptides and for peptide cyclisation via aliphatic thioether crosslinks, including customising macrocycles to stabilise helical peptides for enhanced uptake and delivery to proteins inside cells. Chemoselective and efficient late-stage Zn 2 + -promoted cysteine alkylation in unprotected peptides and proteins promises many useful applications.

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Late‐Stage Hydrocarbon Conjugation and Cyclisation in Synthetic Peptides and Proteins

2021

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Chemical Synthesis of Peptides and Proteins Bearing Base‐Labile Post‐Translational Modifications: Evolution of the Methods in Four Decades

2023

ChemBioChem

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The S‐palmitoylation on Cys residue and O‐acetylation on Ser/Thr residues are two types of base‐labile post‐translational modifications (PTMs) in cells. The lability of these PTMs to bases and nucleophiles makes the peptides/proteins bearing S‐palmitoyl or O‐acetyl groups challenging synthetic targets, which cannot be prepared via the standard Fmoc‐SPPS and native chemical ligation. In this review, we summarized the efforts towards their preparation in the past 40 years, with the focus on the evolution of synthetic methods.

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Chemical Synthesis and Biological Function of Lipidated Proteins

Yang

Zhao

2014

Topics in Current Chemistry

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Lipidated proteins play a key role in many essential biological processes in eukaryotic cells, including signal transduction, membrane trafficking, immune response and pathology. The investigation of the function of lipidated proteins requires access to a reasonable amount of homogenous lipid-modified proteins with defined structures and functional groups. Chemical approaches have provided useful tools to perform such studies. In this review we summarize synthetic methods of lipidated peptides and developments in the chemoselective ligation for the production of lipidated proteins. We introduce the biology of lipidated proteins and highlight the application of synthetic lipidated proteins to tackle important biological questions.

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Lipidation of Peptides and Proteins

Cited by 3 publications

References 260 publications

Late‐Stage Hydrocarbon Conjugation and Cyclisation in Synthetic Peptides and Proteins

Late‐Stage Hydrocarbon Conjugation and Cyclisation in Synthetic Peptides and Proteins

Chemical Synthesis of Peptides and Proteins Bearing Base‐Labile Post‐Translational Modifications: Evolution of the Methods in Four Decades

Chemical Synthesis and Biological Function of Lipidated Proteins

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