Water-driven chemoselective reaction of squarate derivatives with amino acids and peptides.
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.
Sejwal
Preeti
P
Department of Chemistry, Syracuse University, Syracuse, NY 13244-4100, USA.
Han
Yongbin
Y
Shah
Akshay
A
Luk
Yan-Yeung
YY
D000596:Amino Acids / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D012997:Solvents; D014867:Water / Q000737:chemistry*
D000596:Amino Acids; D010455:Peptides; D012997:Solvents; D014867:Water