Accelerating chemoselective peptide bond formation using bis(2-selenylethyl)amido peptide selenoester surrogates† †Electronic supplementary information (ESI) available: Calculations, synthetic protocols and characterization for all compounds. See DOI: 10.1039/c5sc03459k Click here for additional data file.

Accelerating chemoselective peptide bond formation using bis(2-selenylethyl)amido peptide selenoester surrogates.

Given the potential of peptide selenoesters for protein total synthesis and the paucity of methods for the synthesis of these sensitive peptide derivatives, we sought to explore the usefulness of the bis(2-selenylethyl)amido (SeEA) group, i.e. the selenium analog of the bis(2-sulfanylethyl)amido (SEA) group, for accelerating peptide bond formation. A chemoselective exchange process operating in...

Synthesis and stabilities of peptide-based [1]rotaxanes: molecular grafting onto lasso peptide scaffolds† †Electronic supplementary information (ESI) available: Experimental procedures and analytical data of all new compounds. CCDC 1520783. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc00021a Click here for additional data file. Click here for additional data file.

Rapid access to substituted 2-naphthyne intermediates via the benzannulation of halogenated silylalkynes† †Electronic supplementary information (ESI) available: Synthetic procedures, characterization data, and DFT calculations. CCDC 1539450 and 1539451. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc01625e Click here for additional data file. Click here for additional data file.

Orthogonal halogen and hydrogen bonds involving a peptide bond model† †Electronic supplementary information (ESI) available: Experimental part, DSC, IR spectroscopic and crystallographic data. CCDC 899779–899785. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4ce01514b Click here for additional data file. Click here for additional data file.

The peptide bond model N-methylacetamide self-assembles with a range of dihalotetrafluorobenzenes forming co-crystals that all show the occurrence of orthogonal hydrogen and halogen bonds.

Double quick, double click reversible peptide “stapling”† †Electronic supplementary information (ESI) available: Synthesis and characterization, additional biophysical and biochemical analyses. See DOI: 10.1039/c7sc01342f Click here for additional data file. Click here for additional data file. Click here for additional data file.

Synthesis of S peptides......................................................................................................................... 4 WT-S peptide – 8 ................................................................................................................................ 5 OX-S-Cys peptide – 2c ...................................................................................