Epimerization-free access to C-terminal cysteine peptide acids, carboxamides, secondary amides, and esters via complimentary strategies† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc03553e

Serine promoted synthesis of peptide thioester-precursor on solid support for native chemical ligation† †Electronic supplementary information (ESI) available: Experimental procedures and analytical data for new compounds. See DOI: 10.1039/c6sc02162j Click here for additional data file.

Fmoc solid phase peptide synthesis of thioesters for the chemical synthesis of proteins via native chemical ligation is a challenge. We have developed a versatile approach for direct synthesis of peptide thioesters from a solid support utilizing Fmoc chemistry. Peptide thioester synthesis is performed by the formation of a cyclic urethane moiety via a selective reaction of the backbone amide ch...

Bypassing the proline/thiazoline requirement of the macrocyclase PatG† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7cc06550g

Biocatalysis is a fast developing field in which an enzyme's natural capabilities are harnessed or engineered for synthetic chemistry. The enzyme PatG is an extremely promiscuous macrocyclase enzyme tolerating both non-natural amino acids and non-amino acids within the substrate. It does, however, require a proline or thiazoline at the C-terminal position of the core peptide which means the fin...

Cobalt-catalysed C–H carbonylative cyclisation of aliphatic amides† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc05581h Click here for additional data file.

A cobalt-catalysed C-H carbonylation of aliphatic carboxamide derivatives is described, employing commercially available Co(ii)-salts in the presence of a silver oxidant. This operationally simple process utilises an atmospheric pressure of CO and generates a range of substituted succinimide products bearing diverse functional groups that can be successfully accessed via this methodology.

Crystallization-induced dual emission from metal- and heavy atom-free aromatic acids and esters† †Electronic supplementary information (ESI) available. CCDC 1044990 and 1044991. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc00253b Click here for additional data file. Click here for additional data file. Click here for additional data file. Click here for additional data file.

Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki–Miyaura cross-coupling† †Electronic supplementary information (ESI) available: Catalyst optimization data; experimental procedures; compound characterization data; spectra. See DOI: 10.1039/c7sc01093a

The rhodium-catalyzed, directed catalytic asymmetric hydroboration of g,d-unsaturated amides affords a direct route to chiral acyclic secondary g-borylated carbonyl derivatives in high enantiomeric purity. In contrast to a similar b-borylated amide derivative, the g-borylated amide undergoes Suzuki–Miyaura cross-coupling with stereoretention. The utility of the boronic ester products is further...