title: Gram scale de novo synthesis of 2,4-diacetamido-2,4,6-trideoxy-D-galactose.
abstract: In contrast to the infection with Gram-negative bacteria, the precise mechanism of infection with their Gram-positive counterparts is still poorly understood. It has been established, that teichoic and lipoteichoic acids play an important role in host-pathogen interaction. The bacterium Streptococcus pneumoniae is one of the severe life-threatening Gram-positive pathogens and elucidation of the structure of its lipoteichoic acid revealed 2,4-diacetamido-2,4,6-trideoxy-d-galactose as a main component of the cell wall glycopolymer. Our approach toward this carbohydrate used an l-threonine derived aldehyde as starting material following the Garner protocol, which was subjected to a nitro aldol reaction with 2-nitroacetaldehyde diethylacetal to generate the galacto configurated carbon backbone. Subsequent reduction of the nitro group and peracetylation of the molecule resulted in a fully and orthogonally protected derivative, which was deprotected by a single step in pure deionized water at elevated temperatures.
authors.affiliation: Department of Organic Chemistry, University of Vienna, Währingerstraße 38, A-1090 Vienna, Austria.
authors.forename: Christoph
authors.initials: C
authors.lastname: Schmölzer
authors.forename: Christina
authors.initials: C
authors.lastname: Nowikow
authors.forename: Hanspeter
authors.initials: H
authors.lastname: Kählig
authors.forename: Walther
authors.initials: W
authors.lastname: Schmid
mesh_terms: D005690:Galactose / Q000031:analogs & derivatives / Q000737:chemistry* / Q000378:metabolism*; D008070:Lipopolysaccharides / Q000737:chemistry; D015394:Molecular Structure; D013296:Streptococcus pneumoniae / Q000378:metabolism*; D013682:Teichoic Acids / Q000737:chemistry
chemical_list: D008070:Lipopolysaccharides; D013682:Teichoic Acids; C009900:lipoteichoic acid; D005690:Galactose