title: Tandem ligation at X-Cys and Gly-Gly positions via an orthogonally protected auxiliary group.
abstract: 4,5-dimethoxy-2-mercaptobenzylamine (Dmmb) has been protected by acetamidomethyl (Acm) and incorporated into a peptide thioester for use in tandem native chemical ligation. Upon ligation between the thioester and a Cys-peptide, Acm was removed from Dmmb using silver acetate, and a second ligation reaction was done at the Dmmb position. Dmmb removal using TFMSA-TFA effected overall tandem ligation at X-Cys and Gly-Gly.
authors.affiliation: Novo Nordisk Park D9.1.08, DK-2760 Maaloev, Denmark.
authors.forename: Jane C
authors.initials: JC
authors.lastname: Spetzler
authors.forename: Thomas
authors.initials: T
authors.lastname: Hoeg-Jensen
mesh_terms: D000818:Animals; D003545:Cysteine / Q000737:chemistry*; D005998:Glycine / Q000737:chemistry*; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009419:Nerve Tissue Proteins / Q000138:chemical synthesis / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D013552:Swine
chemical_list: D009419:Nerve Tissue Proteins; D010455:Peptides; D003545:Cysteine; D005998:Glycine