title: Efficient Site-Specific Incorporation of Thioamides into Peptides on a Solid Support.
abstract: Designing bioactive peptides containing "thioamide" functionality to modulate their pharmacological properties has been thwarted so far because of various synthetic challenges. The fast, efficient, and inexpensive synthesis and incorporation of a wide range of thionated amino acids into a growing peptide chain on a solid support is reported using standard Fmoc-based chemistry. The commonly employed methodology is comprehensively investigated and optimized with significant improvements regarding the quantity of reagents and reaction conditions. The utility of the protocol is further demonstrated in the synthesis of dithionated linear and monothionated cyclic peptides, which has been a daunting task.
authors.affiliation: Molecular Biophysics Unit, Indian Institute of Science, Bangalore 560012, India.
authors.forename: Somnath
authors.initials: S
authors.lastname: Mukherjee
authors.affiliation: Molecular Biophysics Unit, Indian Institute of Science, Bangalore 560012, India.
authors.forename: Hitesh
authors.initials: H
authors.lastname: Verma
authors.affiliation: Molecular Biophysics Unit, Indian Institute of Science, Bangalore 560012, India.
authors.forename: Jayanta
authors.initials: J
authors.lastname: Chatterjee
mesh_terms: D007202:Indicators and Reagents / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013854:Thioamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D007202:Indicators and Reagents; D010455:Peptides; D010456:Peptides, Cyclic; D013854:Thioamides