Facile chemoselective synthesis of dehydroalanine-containing peptides.
Useful methodology is described for the synthesis of dehydroalanine residues (II) within peptides. The unnatural amino acid (Se)-phenylselenocysteine (I) can be incorporated into growing peptide chains via standard peptide synthesis procedures. Subsequent oxidative elimination affords a dehydroalanine at the desired position. The oxidation conditions are mild and tolerate functionalities commonly found in peptides, including variously protected cysteine residues. To illustrate its utility, cyclic lanthionines have been synthesized by this method.
Okeley
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NM
Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA.
Zhu
Y
Y
van Der Donk
W A
WA
D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D017279:Selenocysteine / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism
D010455:Peptides; C418325:phenylselenocysteine; D017279:Selenocysteine; C015102:dehydroalanine; D000409:Alanine