Synthesis of an alpha-kojibiosyl substituted glycerol teichoic acid hexamer.
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 were coupled to a fully protected glycerol TA hexamer, using chemistry that can be amended for future automated synthesis. Global deprotection afforded the target hexamer kojibiosyl-glycerol containing TA (1).
Hogendorf
Wouter F J
WF
Leiden Institute of Chemistry, Leiden University, 2300 RA Leiden, The Netherlands.
Bos
Leendert J Van den
LJ
Overkleeft
Herman S
HS
Codée
Jeroen D C
JD
Marel
Gijsbert A Van der
GA
D019281:Dimerization; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D013293:Enterococcus faecalis / Q000737:chemistry; D005990:Glycerol; D009943:Organophosphorus Compounds; D013682:Teichoic Acids / Q000138:chemical synthesis* / Q000737:chemistry
D004187:Disaccharides; D009943:Organophosphorus Compounds; D013682:Teichoic Acids; C434331:phosphoramidite; C008237:kojibiose; D005990:Glycerol