Synthesis and utility of β-selenol-phenylalanine for native chemical ligation-deselenization chemistry.
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.
School of Chemistry, The University of Sydney, NSW 2006, Australia.
Lara R
LR
Malins
Richard J
RJ
Payne
D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry; D010649:Phenylalanine / Q000138:chemical synthesis*; D012643:Selenium / Q000737:chemistry*; D018036:Selenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D010455:Peptides; D018036:Selenium Compounds; C442270:selenol; D010649:Phenylalanine; D012643:Selenium