Protecting Triazabutadienes To Afford Acid Resistance. (21st October 2016)

• Record Type: Journal Article
• Authors: Guzman, Lindsay E.; Kimani, Flora W.; Jewett, John C.
• Is Part Of: Chembiochem. Volume 17:Number 23(2016)
• Page Start: 2220
• Page End: 2222
• Publication Date: 2016-10-21
• Subjects: acid/base chemistry -- aryl diazonium ion -- hydrolysis -- protecting groups -- solid-phase synthesis; Biochemistry -- Periodicals; Molecular biology -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1002/cbic.201600517
• Languages: English
• ISSNs: 1439-4227

Abstract

Abstract: Recent work on triazabutadienes has shown that they have the ability to release aryl diazonium ions under exceptionally mild acidic conditions. There are instances that require that this release be prevented or minimized. Accordingly, a base‐labile protection strategy for the triazabutadiene is presented. It affords enhanced synthetic and practical utility of the triazabutadiene. The effects of steric and electronic factors in the rate of removal are discussed, and the triazabutadiene protection is shown to be compatible with the traditional acid‐labile protection strategy used in solid phase peptide synthesis. Abstract : Behind the mask : Triazabutadienes can be used as masked tyrosine‐selective aryl diazonium ions. We report a base‐labile protecting group for triazabutadienes to prevent the acid‐dependent release of aryl diazonium ions. The pH‐dependent deprotection rate constants are reported, thus enabling widespread use of triazabutadienes in chemical biology.