title: A palladium and gold catalytic system enables direct access to O- and S-linked non-natural glyco-conjugates.
abstract: Here we report a straightforward cross-coupling method for the synthesis of non-natural glycoamino acids from alkyne-bearing monosaccharides and p-iodophenylalanine. Pd/Au-catalyzed Sonogashira coupling is tolerant to both O- and S-glycosides without any epimerization. In addition, no racemization of the amino acid was observed allowing direct access to the homogeneous glyco-conjugate in a single step. Notably, this Pd/Au catalytic system presents enhanced catalytic activity than conventional Pd/Cu and Pd-only platforms, and it further enables the convergent synthesis of glycodipeptides.
authors.affiliation: School of Energy and Chemical Engineering, Ulsan National Institute of Science and Technology (UNIST), UNIST-gil 50, Ulsan 689-798, Republic of Korea. syhong@unist.ac.kr.
authors.forename: Min Ho
authors.initials: MH
authors.lastname: Jeon
authors.forename: Bijoy P
authors.initials: BP
authors.lastname: Mathew
authors.forename: Malleswara Rao
authors.initials: MR
authors.lastname: Kuram
authors.forename: Kyungjae
authors.initials: K
authors.lastname: Myung
authors.forename: Sung You
authors.initials: SY
authors.lastname: Hong
mesh_terms: D002384:Catalysis; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D006046:Gold / Q000737:chemistry*; D008968:Molecular Conformation; D010165:Palladium / Q000737:chemistry*
chemical_list: D006001:Glycoconjugates; D010165:Palladium; D006046:Gold