Chemical synthesis of proteins and circular peptides using Nalpha-(1-phenyl-2-mercaptoethyl) auxiliaries.
An overview of the applications of Nalpha-(1-phenyl-2-mercaptoethyl) auxiliary is presented. We describe the on resin preparation (Calpha-carboxy and thioester) of Nalpha-auxiliary derivatives of glycine and the synthesis and incorporation of preformed Nalpha-auxiliary derivatives of glycine and alanine with the protection schemes, including the thiazolidine strategy for SPPS. Such approaches allowed the synthesis of the protein cytochrome b562 as well as native circular peptides after successful removal of the auxiliary.
Botti
Paolo
P
Department of Structural Biology and Bioinformatics, University of Geneva, 1 rue Michel Servet, 1211 Geneva 4, Switzerland. Paolo.Botti@medecine.unige.ch
Tchertchian
Sylvie
S
D000409:Alanine / Q000138:chemical synthesis / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D005998:Glycine / Q000138:chemical synthesis / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011506:Proteins / Q000138:chemical synthesis* / Q000737:chemistry; D012117:Resins, Synthetic / Q000138:chemical synthesis / Q000737:chemistry
D000596:Amino Acids; D010455:Peptides; D011506:Proteins; D012117:Resins, Synthetic; D000409:Alanine; D005998:Glycine