Water-Driven Chemoselective Reaction of Squarate Derivatives with Amino Acids and Peptides
- 12 October 2007
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (23), 4897-4900
- https://doi.org/10.1021/ol702275q
Abstract
Here, we report a new class of highly chemoselective reactions between squarate derivatives and the amino acid cysteine or unprotected peptides with a N-terminus cysteine that proceed most efficiently in entirely aqueous solution at neutral pH. Kinetic and structural studies reveal that the presence of hydrogen bonding in water is primarily responsible for both the high yield and fast rate of the reaction.Keywords
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