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Benzoisothiazolone (BIT): A Fast, Efficient, and Recyclable Redox Reagent for Solid Phase Peptide Synthesis
Author(s) -
Bukya Hemalatha,
Nayani Kiranmai,
Gangireddy Pavankumar,
Mainkar Prathama S.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000722
Subject(s) - chemistry , combinatorial chemistry , reagent , peptide , peptide synthesis , solid phase synthesis , redox , organic chemistry , biochemistry
Solid‐phase peptide synthesis (SPPS), a preferred synthetic procedure, generates by‐products and effluents in multiple equivalents for one equivalent of desired product. Presented herein is the use of a fast and efficient coupling protocol for SPPS using a benzoisothiazolone (BIT), which can be fully recycled. The BIT, as redox activator, works under very mild conditions and generates minimal amount of waste. As a case study, the BIT coupling protocol is applied to the synthesis of side chain of the recently discovered antibiotic, teixobactin.