The pKa of Brønsted acids controls their reactivity with diazo compounds. Issue 47 (23rd May 2016)

• Record Type: Journal Article
• Authors: Fei, Na; Sauter, Basilius; Gillingham, Dennis
• Is Part Of: Chemical communications. Volume 52:Issue 47(2016)
• Page Start: 7501
• Page End: 7504
• Publication Date: 2016-05-23
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c6cc03561b
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : We study the O -alkylation of phosphate groups by alkyl diazo compounds in a range of small molecules and biopolymers. Abstract : We study the O -alkylation of phosphate groups by alkyl diazo compounds in a range of small molecules and biopolymers. We show that the relatively high p K a of phosphate in comparison to the other naturally occurring Brønsted acids can be exploited to control alkylation selectivity. We provide a simple protocol for chemical modification of some of the most important instances of phosphates in natural compounds including in small molecule metabolites, nucleic acids, and peptides.