Synthetic methodology towards allylic trans -cyclooctene-ethers enables modification of carbohydrates: bioorthogonal manipulation of the lac repressor

Chemical Science, vol. 11, pp. 10175–10179

Abstract

Two novel reagents were developed to direct formation of allylic cis -cyclooctene (CCO) ethers, followed by photochemical isomerization to obtain trans -cyclooctene (TCO) ethers. The method was used to cage a bio-active carbohydrate.

Authors 5

1. Mark A. R. de Geus Aachen Leiden Institute of Chemistry Leiden Institute of Chemistry, The Institute for Chemical Immunology

   Leiden University

   Affiliation as printed

   2333 CC Leiden

   Leiden Institute of Chemistry

   Leiden University

   The Institute for Chemical Immunology

   The Netherlands

   Leiden Institute of Chemistry, The Institute for Chemical Immunology, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands

2. G. J. Mirjam Groenewold Aachen Leiden Institute of Chemistry Leiden Institute of Chemistry, The Institute for Chemical Immunology

   Leiden University

   Affiliation as printed

   2333 CC Leiden

   Leiden Institute of Chemistry

   Leiden University

   The Institute for Chemical Immunology

   The Netherlands

   Leiden Institute of Chemistry, The Institute for Chemical Immunology, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands

3. Elmer Maurits Aachen Leiden Institute of Chemistry Leiden Institute of Chemistry, The Institute for Chemical Immunology

   Leiden University

   Affiliation as printed

   2333 CC Leiden

   Leiden Institute of Chemistry

   Leiden University

   The Institute for Chemical Immunology

   The Netherlands

   Leiden Institute of Chemistry, The Institute for Chemical Immunology, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands

4. Can Araman corresponding Aachen Leiden Institute of Chemistry Leiden Institute of Chemistry, The Institute for Chemical Immunology

   Leiden University

   Affiliation as printed

   2333 CC Leiden

   Leiden Institute of Chemistry

   Leiden University

   The Institute for Chemical Immunology

   The Netherlands

   Leiden Institute of Chemistry, The Institute for Chemical Immunology, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands

5. Sander I. van Kasteren corresponding Aachen Leiden Institute of Chemistry

   Leiden University

   Affiliation as printed

   2333 CC Leiden

   Leiden Institute of Chemistry

   Leiden University

   The Institute for Chemical Immunology

   The Netherlands