Journal article
The pKa of Brønsted acids controls their reactivity with diazo compounds.
- Fei N Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056, Basel, Switzerland. dennis.gillingham@unibas.ch.
- Sauter B
- Gillingham D
- 2016-05-24
Published in:
- Chemical communications (Cambridge, England). - 2016
English
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.
- Language
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- English
- Open access status
- hybrid
- Identifiers
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- DOI 10.1039/c6cc03561b
- PMID 27212133
- Persistent URL
- https://sonar.ch/global/documents/53452
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