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Utilization of bench-stable and readily available nickel(II) triflate for access to 1,2-cis-2-aminoglycosides.
Sletten, Eric T; Ramadugu, Sai Kumar; Nguyen, Hien M.
Afiliação
  • Sletten ET; Department of Chemistry, University of Iowa, Iowa City, 52242, USA.
  • Ramadugu SK; Iowa Informatics Initiative, University of Iowa, Iowa City, 52242, USA.
  • Nguyen HM; Department of Chemistry, University of Iowa, Iowa City, 52242, USA. Electronic address: hien-nguyen@uiowa.edu.
Carbohydr Res ; 435: 195-207, 2016 Nov 29.
Article em En | MEDLINE | ID: mdl-27816838
The utilization of substoichiometric amounts of commercially available nickel(II) triflate as an activator in the reagent-controlled glycosylation reaction for the stereoselective construction of biologically relevant targets containing 1,2-cis-2-amino glycosidic linkages is reported. This straightforward and accessible methodology is mild, operationally simple and safe through catalytic activation by readily available Ni(OTf)2 in comparison to systems employing our previously in-house prepared Ni(4-F-PhCN)4(OTf)2. We anticipate that the bench-stable and inexpensive Ni(OTf)2, coupled with little to no extra laboratory training to set up the glycosylation reaction and no requirement of specialized equipment, should make this methodology be readily adopted by non-carbohydrate specialists. This report further highlights the efficacy of Ni(OTf)2 to prepare several bioactive motifs, such as blood type A-type V and VI antigens, heparin sulfate disaccharide repeating unit, aminooxy glycosides, and α-GalNAc-Serine conjugate, which cannot be achieved in high yield and α-selectivity utilizing in-house prepared Ni(4-F-PhCN)4(OTf)2 catalyst. The newly-developed protocol eliminates the need for the synthesis of Ni(4-F-PhCN)4(OTf)2 and is scalable and reproducible. Furthermore, computational simulations in combination with 1H NMR studies analyzed the effects of various solvents on the intramolecular hydrogen bonding network of tumor-associated mucin Fmoc-protected GalNAc-threonine amino acid antigen derivative, verifying discrepancies found that were previously unreported.
Assuntos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Aminoglicosídeos / Níquel Idioma: En Revista: Carbohydr Res Ano de publicação: 2016 Tipo de documento: Article País de afiliação: Estados Unidos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Aminoglicosídeos / Níquel Idioma: En Revista: Carbohydr Res Ano de publicação: 2016 Tipo de documento: Article País de afiliação: Estados Unidos