title: 5-Methylisoxazole-3-carboxamide-Directed Palladium-Catalyzed γ-C(sp(3))-H Acetoxylation and Application to the Synthesis of γ-Mercapto Amino Acids for Native Chemical Ligation.
abstract: Palladium-catalyzed acetoxylation of the primary γ-C(sp(3))-H bonds in the amino acids Val, Thr, and Ile was achieved using a newly discovered 5-methylisoxazole-3-carboxamide directing group. The γ-acetoxylated α-amino acid derivatives could be easily converted to γ-mercapto amino acids, which are useful for native chemical ligation (NCL). The first application of NCL at isoleucine in the semisynthesis of a Xenopus histone H3 protein was also demonstrated.
authors.affiliation: School of Biological Sciences, Nanyang Technological University , Singapore 637551.
authors.forename: Kalyan Kumar
authors.initials: KK
authors.lastname: Pasunooti
authors.affiliation: School of Biological Sciences, Nanyang Technological University , Singapore 637551.
authors.forename: Renliang
authors.initials: R
authors.lastname: Yang
authors.affiliation: School of Biological Sciences, Nanyang Technological University , Singapore 637551.
authors.forename: Biplab
authors.initials: B
authors.lastname: Banerjee
authors.affiliation: School of Biological Sciences, Nanyang Technological University , Singapore 637551.
authors.forename: Terence
authors.initials: T
authors.lastname: Yap
authors.affiliation: School of Biological Sciences, Nanyang Technological University , Singapore 637551.
authors.forename: Chuan-Fa
authors.initials: CF
authors.lastname: Liu
mesh_terms: D000595:Amino Acid Sequence; D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D006657:Histones / Q000737:chemistry; D006860:Hydrogen Bonding; D007555:Isoxazoles / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D029867:Xenopus Proteins / Q000737:chemistry
chemical_list: C000606655:5-methylisoxazole-3-carboxamide; D000596:Amino Acids; D006657:Histones; D007555:Isoxazoles; D029867:Xenopus Proteins; D010165:Palladium