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Synthesis of an alpha-kojibiosyl substituted glycerol teichoic acid hexamer.

Bioorg. Med. Chem.. 2010; 
HogendorfWouter F J,BosLeendert J Van den,OverkleeftHerman S,CodéeJeroen D C,MarelGijsbert A Van
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Gene Synthesis … with an automated solid-phase approach, and we are currently studying the efficiency of this in the solid-phase synthesis of differentially substituted TAs. 4. Experimental. 4.1. General. All chemicals (Acros, Fluka, Merck, Schleicher & Schuell, Sigma–Aldrich, Genscript) were used … Get A Quote

摘要

In this paper the synthesis of an Enterococcus Faecalis teichoic acid (TA) hexamer is presented. The key kojibiosyl-glycerol phosphoramidite building block was obtained by condensation of thioglucose donors, provided with various protecting groups at the C2 hydroxyl function with an orthogonally protected glycerol acceptor. After selective deprotection, the resulting 1,2-cis-linked pseudodisaccharide acceptor was coupled to an alpha-directing thioglucose donor, giving the corresponding pseudotrisaccharide, which is then transformed to a phosphoramidite synthon. The kojibiosyl-glycerol phosphoramidite in combination with a glycerolphosphoramidite, an aminohexylphosphoramidite and dibenzylglycerol wer... More

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