1377320-82-5Relevant academic research and scientific papers
Synthesis and Utility of β-Selenophenylalanine and β-Selenoleucine in Diselenide-Selenoester Ligation
Corcilius, Leo,Payne, Richard J.,Premdjee, Bhavesh,Wang, Xiaoyi
, (2020)
The synthesis of suitably protected β-selenophenylalanine and β-selenoleucine amino acids was accomplished from Garner's aldehyde as a common starting point. These selenoamino acids were incorporated into model peptides and shown to facilitate rapid diselenide-selenoester ligation (DSL) with peptide selenoesters which, when coupled with in situ deselenization, afforded native peptide products. The utility of one-pot DSL-deselenization chemistry at phenylalanine and leucine was demonstrated through the rapid synthesis of a glycosylated interferon-γfragment and the chemokine-binding protein UL22A, respectively.
Synthesis and utility of β-selenol-phenylalanine for native chemical ligation-deselenization chemistry
Malins, Lara R.,Payne, Richard J.
, p. 3142 - 3145 (2012/10/07)
An efficient synthetic route to a suitably protected β-selenol- phenylalanine derivative from commercially available Garner's aldehyde is described. The incorporation of this building block into peptides and its application in native chemical ligation reactions with peptide thioesters are demonstrated. Ligation products were chemoselectively deselenized (including in the presence of unprotected cysteine residues) to provide native peptides.
