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The pKa of Bronsted acids controls their reactivity with diazo compounds

Fei, Na and Sauter, Basilius and Gillingham, Dennis. (2016) The pKa of Bronsted acids controls their reactivity with diazo compounds. Journal of the Chemical Society, Chemical Communications, 52. pp. 7501-7504.

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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 pKa 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.
Faculties and Departments:05 Faculty of Science
05 Faculty of Science > Departement Chemie
05 Faculty of Science > Departement Chemie > Chemie > Organische Chemie (Gillingham)
UniBasel Contributors:Gillingham, Dennis and Sauter, Basilius
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Royal Society of Chemistry
ISSN:1359-7345
e-ISSN:1364-548X
Note:Publication type according to Uni Basel Research Database: Journal article
Language:English
Identification Number:
Last Modified:17 Mar 2017 14:04
Deposited On:23 Feb 2017 15:42

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