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Angewandte Chemie. international edition v.57 no.27, 2018년, pp.8240 - 8244   SCI SCIE
본 등재정보는 저널의 등재정보를 참고하여 보여주는 베타서비스로 정확한 논문의 등재여부는 등재기관에 확인하시기 바랍니다.

Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity

van der Vorm, Stefan (Bioorganic Synthesis Department, Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC, Leiden, The Netherlands ) ; van Hengst, Jacob M. A. (Bioorganic Synthesis Department, Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC, Leiden, The Netherlands ) ; Bakker, Marloes (Bioorganic Synthesis Department, Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC, Leiden, The Netherlands ) ; Overkleeft, Herman S. (Bioorganic Synthesis Department, Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC, Leiden, The Netherlands ) ; van der Marel, Gijsbert A. (Bioorganic Synthesis Department, Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC, Leiden, The Netherlands ) ; Codée, Jeroen D. C. (Bioorganic Synthesis Department, Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC, Leiden, The Netherlands ) ;
  • 초록  

    Abstract The reactivity of both coupling partners—the glycosyl donor and acceptor—is decisive for the outcome of a glycosylation reaction, in terms of both yield and stereoselectivity. Where the reactivity of glycosyl donors is well understood and can be controlled through manipulation of the functional/protecting‐group pattern, the reactivity of glycosyl acceptor alcohols is poorly understood. We here present an operationally simple system to gauge glycosyl acceptor reactivity, which employs two conformationally locked donors with stereoselectivity that critically depends on the reactivity of the nucleophile. A wide array of acceptors was screened and their structure–reactivity/stereoselectivity relationships established. By systematically varying the protecting groups, the reactivity of glycosyl acceptors can be adjusted to attain stereoselective cis ‐glucosylations.


  • 주제어

    acceptor reactivity .   enzyme mechanisms .   glycosylation .   reactivity tuning .   stereoselectivity.  

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