Peptides: The Wave of the Future pp 269-270 | Cite as
Oxidation of Threonine and Serine Residues on Solid-Phase: Pyrazine Formation by Dess-Martin Periodinane Oxidation
Abstract
In recent years, solid phase synthesis has emerged as a powerful tool for creating large numbers of highly diverse compounds for utilization in various screening protocols. Libraries of organic molecules and peptides have proven to be highly efficient for the discovery process of new therapeutic lead compounds [1]. During the course of studies on carbonyl-formation on solid phase [2], we were interested in the oxidation of threonine and serine residues in a peptide on solid phase for the cyclization to a pyrazine ring. Dess-Martin periodinane (DMP) has been used for facile and efficient oxidations of primary and secondary alcohols to aldehydes and ketones, respectively, in solution [3]. It was expected that applying the Dess-Martin periodinane oxidation on solid phase would result in a novel pyrazine formation when a penultimate N-terminated threonine or serine was oxidized.
Keywords
Serine Residue Secondary Alcohol Solid Phase Synthesis Efficient Oxidation Screen ProtocolReferences
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