Water-driven chemoselective reaction of squarate derivatives with amino acids and peptides

Preeti Sejwal, Yongbin Han, Akshay Shah, Yan Yeung Luk

Research output: Contribution to journalArticle

22 Scopus citations

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish (US)
Pages (from-to)4897-4900
Number of pages4
JournalOrganic Letters
Volume9
Issue number23
DOIs
StatePublished - Nov 8 2007

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ASJC Scopus subject areas

  • Molecular Medicine

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