title: Thioacetic acid/NaSH-mediated synthesis of N-protected amino thioacids and their utility in peptide synthesis.
abstract: Thioacids are recently gaining momentum due to their versatile reactivity. The reactivity of thioacids has been widely explored in the selective amide/peptide bond formation. Thioacids are generally synthesized from the reaction between activated carboxylic acids such as acid chlorides, active esters, etc., and Na2S, H2S, or NaSH. We sought to investigate whether the versatile reactivity of the thioacids can be tuned for the conversion of carboxylic acids into corresponding thioacids in the presence of NaSH. Herein, we report that thioacetic acid- and NaSH-mediated synthesis of N-protected amino thioacids from the corresponding N-protected amino acids, oxidative dimerization of thioacids, crystal conformations of thioacid oxidative dimers, and the utility of thioacids and oxidative dimers in peptide synthesis. Our results suggest that peptides can be synthesized without using standard coupling agents.
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research , Dr. Homi Bhabha Road, Pune 411 008, India.
authors.forename: Sachitanand M
authors.initials: SM
authors.lastname: Mali
authors.forename: Hosahudya N
authors.initials: HN
authors.lastname: Gopi
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013457:Sulfur Compounds / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D010455:Peptides; D013438:Sulfhydryl Compounds; D013457:Sulfur Compounds; C005732:thioacetic acid