Fluorous linker facilitated synthesis of teichoic acid fragments

Wouter F J Hogendorf; Lucien N Lameijer; Thomas J M Beenakker; Herman S Overkleeft; Dmitri V Filippov; Jeroen D C Codée; Gijsbert A Van der Marel

doi:10.1021/ol2033652

Fluorous linker facilitated synthesis of teichoic acid fragments

Org Lett. 2012 Feb 3;14(3):848-51. doi: 10.1021/ol2033652. Epub 2012 Jan 20.

Authors

Wouter F J Hogendorf¹, Lucien N Lameijer, Thomas J M Beenakker, Herman S Overkleeft, Dmitri V Filippov, Jeroen D C Codée, Gijsbert A Van der Marel

Affiliation

¹ Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.

PMID: 22264133
DOI: 10.1021/ol2033652

Abstract

The use of perfluorooctylpropylsulfonylethanol as a new phosphate protecting group and fluorous linker is evaluated in the stepwise solution phase synthesis of a number of biologically relevant (carbohydrate substituted) glycerol teichoic acid fragments. Teichoic acid fragments, up to the dodecamer level, were assembled by means of phosphoramidite chemistry, using a relatively small excess of the building blocks and a repetitive efficient purification procedure of the protected intermediates by fluorous solid phase extraction (F-SPE).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Fluorine / chemistry*
Glucosamine / chemistry
Molecular Structure
Teichoic Acids / chemical synthesis*

Substances

Teichoic Acids
Fluorine
Glucosamine