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Themed collection Selective Chemistry with Peptides and Proteins

26 items
Review Article

Bioconjugation – using selective chemistry to enhance the properties of proteins and peptides as therapeutics and carriers

Both peptide and protein therapeutics are becoming increasingly important for treating a wide range of diseases. Functionalisation of these via site-selective chemical modification leads to enhancement of their therapeutic properties.

Graphical abstract: Bioconjugation – using selective chemistry to enhance the properties of proteins and peptides as therapeutics and carriers
Open Access Review Article

Site-selective incorporation and ligation of protein aldehydes

The incorporation of aldehyde handles into proteins, and subsequent chemical reactions thereof, is rapidly proving to be an effective way of generating homogeneous, covalently linked protein constructs that can display a vast array of functionality.

Graphical abstract: Site-selective incorporation and ligation of protein aldehydes
Review Article

Chemically synthesized glycoconjugates on proteins: effects of multivalency and glycoform in vivo

The biodistributions and in vivo kinetics of chemically prepared glycoconjugates on proteins are reviewed.

Graphical abstract: Chemically synthesized glycoconjugates on proteins: effects of multivalency and glycoform in vivo
Review Article

A strategy for the synthesis of hydrophobic proteins and glycoproteins

The hydrophobic glycoprotein was successfully synthesized by the reverse polarity protection strategy combined with the O-acylisopeptide method, which will be useful for the synthesis of various hydrophobic (glyco)proteins.

Graphical abstract: A strategy for the synthesis of hydrophobic proteins and glycoproteins
Communication

Efficient synthesis of cysteine-rich cyclic peptides through intramolecular native chemical ligation of N-Hnb-Cys peptide crypto-thioesters

We herein introduce a straightforward synthetic route to cysteine-containing cyclic peptides. It is based on the intramolecular native chemical ligation of thioesters generated in situ from N-Hnb-Cys crypto-thioesters. The strategy is applied to a representative range of natural cyclic disulfide-rich peptide sequences.

Graphical abstract: Efficient synthesis of cysteine-rich cyclic peptides through intramolecular native chemical ligation of N-Hnb-Cys peptide crypto-thioesters
Communication

Arginine side-chain modification that occurs during copper-catalysed azide–alkyne click reactions resembles an advanced glycation end product

An adduct of dehydroascorbate with arginine forms during copper-catalysed azide–alkyne click reactions and resembles an advanced glycation end product.

Graphical abstract: Arginine side-chain modification that occurs during copper-catalysed azide–alkyne click reactions resembles an advanced glycation end product
Communication

Efficient synthesis of longer Aβ peptides via removable backbone modification

This paper describes a new method for the efficient chemical synthesis of longer Aβ peptides with the combination of the RBM strategy and native chemical ligation.

Graphical abstract: Efficient synthesis of longer Aβ peptides via removable backbone modification
Open Access Communication

The total synthesis and functional evaluation of fourteen stereoisomers of yaku'amide B. The importance of stereochemistry for hydrophobicity and cytotoxicity

Yaku'amide B is a highly unsaturated linear tridecapeptide and an extremely potent cytotoxin.

Graphical abstract: The total synthesis and functional evaluation of fourteen stereoisomers of yaku'amide B. The importance of stereochemistry for hydrophobicity and cytotoxicity
Communication

Hmboff/on as a switchable thiol protecting group for native chemical ligation

A new thiol protecting group Hmboff/on is described, which has a switchable activity that may be useful in the chemical synthesis of complex proteins or peptides.

Graphical abstract: Hmboff/on as a switchable thiol protecting group for native chemical ligation
Communication

A perfluoroaromatic abiotic analog of H2 relaxin enabled by rapid flow-based peptide synthesis

We report on the rapid-flow based synthesis and functional characterization of a H2 relaxin analog that takes advantage of perfluoroarylation-cysteine SNAr chemistry for a disulfide replacement strategy.

Graphical abstract: A perfluoroaromatic abiotic analog of H2 relaxin enabled by rapid flow-based peptide synthesis
Paper

Chemical synthesis and enzymatic properties of RNase A analogues designed to enhance second-step catalytic activity

Adenine covalently attached to the RNase A enzyme molecule decreased the rate of transphosphorylation and increased the rate of hydrolysis.

Graphical abstract: Chemical synthesis and enzymatic properties of RNase A analogues designed to enhance second-step catalytic activity
Paper

6-Bromo-7-hydroxy-3-methylcoumarin (mBhc) is an efficient multi-photon labile protecting group for thiol caging and three-dimensional chemical patterning

Photochemical release of thiol groups allows spatio-temporal control of biological processes.

Graphical abstract: 6-Bromo-7-hydroxy-3-methylcoumarin (mBhc) is an efficient multi-photon labile protecting group for thiol caging and three-dimensional chemical patterning
Paper

Bis(arylmethyl)-substituted unsymmetrical phosphites for the synthesis of lipidated peptides via Staudinger-phosphite reactions

With this study we introduce new unsymmetrical phosphites to obtain lipidated peptide-conjugates starting from easily accessible azide-modified amino acid or peptide precursors.

Graphical abstract: Bis(arylmethyl)-substituted unsymmetrical phosphites for the synthesis of lipidated peptides via Staudinger-phosphite reactions
Paper

Insight into the SEA amide thioester equilibrium. Application to the synthesis of thioesters at neutral pH

Peptide alkylthioesters can be prepared at neutral pH by bis(2-sulfanylethyl)amide-thiol exchange.

Graphical abstract: Insight into the SEA amide thioester equilibrium. Application to the synthesis of thioesters at neutral pH
Paper

Selenocysteine containing analogues of Atx1-based peptides protect cells from copper ion toxicity

Seleno-substituted model peptides of copper metallochaperone proteins display particularly high Cu(I) affinity and in vitro anti-oxidative reactivity.

Graphical abstract: Selenocysteine containing analogues of Atx1-based peptides protect cells from copper ion toxicity
Paper

Replacing a single atom accelerates the folding of a protein and increases its thermostability

The conformational attributes of proline can have a substantial effect on the folding of polypeptide chains into a native structure and on the stability of that structure.

Graphical abstract: Replacing a single atom accelerates the folding of a protein and increases its thermostability
Paper

Chemoselective modifications for the traceless ligation of thioamide-containing peptides and proteins

Optimized reaction conditions permit selective desulfurization of thiols or deselenization of selenols in the presence of thioamides to enable traceless thioamide incorporation by peptide ligation.

Graphical abstract: Chemoselective modifications for the traceless ligation of thioamide-containing peptides and proteins
Paper

Synthesis and in vitro bone cell activity of analogues of the cyclohexapeptide dianthin G

Dianthin G and its dicarba analogue were both shown to increase the number of human osteoblasts without affecting bone resorption.

Graphical abstract: Synthesis and in vitro bone cell activity of analogues of the cyclohexapeptide dianthin G
Paper

Synthesis of misfolded glycoprotein dimers through native chemical ligation of a dimeric peptide thioester

Misfolded glycoprotein dimers were synthesized through double native chemical ligation between a dimeric peptide-α-thioester, glycopeptide, and non-glycosylated peptide.

Graphical abstract: Synthesis of misfolded glycoprotein dimers through native chemical ligation of a dimeric peptide thioester
Paper

Synthesis of tumor necrosis factor α for use as a mirror-image phage display target

Chemical synthesis of TNFα, a central regulator of inflammation, for use as a mirror-image phage display target.

Graphical abstract: Synthesis of tumor necrosis factor α for use as a mirror-image phage display target
Open Access Paper

Genetic incorporation of 1,2-aminothiol functionality for site-specific protein modification via thiazolidine formation

Thiazolidine ligation was used to modify site-specifically proteins harbouring a 1,2-aminothiol moiety introduced by amber codon suppression technology.

Graphical abstract: Genetic incorporation of 1,2-aminothiol functionality for site-specific protein modification via thiazolidine formation
Paper

Synthesis and amylin receptor activity of glycomimetics of pramlintide using click chemistry

Synthetic clicked pramlintide glycomimetics maintained AMY1(a) activity and are expected to possess superior synthetic and pharmacokinetic properties than N-glycosylated analogues.

Graphical abstract: Synthesis and amylin receptor activity of glycomimetics of pramlintide using click chemistry
Paper

Assessment of reagents for selenocysteine conjugation and the stability of selenocysteine adducts

The allenamide functional group reacts with selenocysteine with notably high efficiency, leads to antibody conjugates with remarkable stability, and shows exquisite selectivity for selenocysteine conjugation.

Graphical abstract: Assessment of reagents for selenocysteine conjugation and the stability of selenocysteine adducts
Open Access Paper

On-resin Diels–Alder reaction with inverse electron demand: an efficient ligation method for complex peptides with a varying spacer to optimize cell adhesion

The DARinv on resin is a new orthogonal reaction in peptide synthesis and the benefits for cell adhesion are discussed.

Graphical abstract: On-resin Diels–Alder reaction with inverse electron demand: an efficient ligation method for complex peptides with a varying spacer to optimize cell adhesion
Open Access Paper

Assessing histidine tags for recruiting deoxyribozymes to catalyze peptide and protein modification reactions

We evaluate the ability of hexahistidine tags to recruit deoxyribozymes for covalently modifying peptides and proteins.

Graphical abstract: Assessing histidine tags for recruiting deoxyribozymes to catalyze peptide and protein modification reactions
Paper

Solid phase oxime ligations for the iterative synthesis of polypeptide conjugates

All on-resin! An efficient C-to-N iterative strategy for solid phase chemical ligations (SPCL).

Graphical abstract: Solid phase oxime ligations for the iterative synthesis of polypeptide conjugates
26 items

About this collection

This themed issue highlights some of the most recent exciting research in the field of peptides and protein chemistry, including native chemical ligation and other chemical reactions to prepare peptides and proteins, and selective peptide and protein modification strategies.

The issue was guest-edited by Professor Philip Dawson (The Scripps Research Institute, USA). New articles will be added to this collection as they are published.

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