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Natural products are privileged scaffolds due to their high propensity to possess bioactivity. To expedite discovery of thiol-containing compounds, we devised a selective solid-supported reagent for their immobilization, followed by cleavage of a photocleavable linker to yield stable natural product conjugates for direct detection by mass spectrometry. Importantly, the natural products can also be tracelessly released to yield the native structures for chemical and biological evaluation. [ABSTRACT FROM AUTHOR]

A polyalanine-based peptide which forms a stable, negatively-charged α-helix in the gas phase is reported. Addition of an N-terminal acidic residue forms a stabilizing hydrogen bond network and an electrostatic interaction with the helical dipole. Formation of this secondary structure was demonstrated using ion mobility-mass spectrometry and molecular modelling techniques. [ABSTRACT FROM AUTHOR]

Shikimic acid can be transformed into monovalent and multivalent glycomimetics that target different members of the C-type lectin class, including DC-SIGN, a dendritic cell lectin that facilitates HIV transmission. [ABSTRACT FROM AUTHOR]

Modified nucleoside triphosphates (NTPs) are invaluable tools to probe bacterial enzymatic mechanisms, develop novel genetic material, and engineer drugs and proteins with new functionalities. Although the impact of nucleobase alterations has predominantly been studied due to their importance for protein recognition, sugar and phosphate modifications have also been investigated. However, NTPs are cell impermeable due to their negatively charged phosphate tail, a major hurdle to achieving live bacterial studies. Herein, we review the recent advances made to investigate and evolve bacteria and their processes with the use of modified NTPs by exploring alterations in one of the three moieties: the nucleobase, the sugar and the phosphate tail. We also present the innovative methods that have been devised to internalize NTPs into bacteria for in vivo applications., Competing Interests: Conflicts of interest There are no conflicts to declare.

The selective reaction of one functional group in the presence of others is not a trivial task. A noteworthy amount of research has been dedicated to the chemoselective reaction of the hydroxyl moiety. This group is prevalent in many biologically important molecules including natural products and proteins. However, targeting the hydroxyl group is difficult for many reasons including its relatively low nucleophilicity in comparison to other ubiquitous functional groups such as amines and thiols. Additionally, many of the developed chemoselective reactions cannot be used in the presence of water. Despite these complications, chemoselective transformation of the hydroxyl moiety has been utilized in the synthesis of complex natural product derivatives, the reaction of tyrosine residues in proteins, the isolation of natural products and is the mechanism of action of myriad drugs. Here, methods for selective targeting of this group, as well as applications of several devised methods, are described.

Natural products account for a significant proportion of modern day therapeutic agents. However, the discovery of novel compounds is hindered by the isolation process, which often relies upon extraction and chromatographic separation techniques. These methods, which are dependent upon the physicochemical properties of the compounds, have a limited ability to both purify and concentrate the minor components of a biological extract. We have devised an isolation strategy based upon an orthogonal chemical feature, namely, functional group composition. Development of a functional group-targeted method is expected to achieve exceptional resolution given the large number of distinct moieties present in natural product extracts. Here, we describe the generation of controllably reversible covalent enrichment tags for the chemoselective isolation of alcohol-containing natural products from complex mixtures.