Peter Waldstätten

Zur struktur der 3-desoxyoctulosonsäure- (KDO-) region des lipopolysaccharids von Salmonella minnesota Re 595

Spectroscopic data (1H- and 13C-N.m.r.) indicate that the tetrasaccharide αdOclAp(2→4)αdOclAp(2→6)βGIcNp(1→6)GlcN is formed upon hydrazinolysis of the lipopolysaccharide from Salmonella minnesota Re 595.

Regiospecific syntheses of azidodeoxy and diazidodideoxy derivatives of methyl α-d-arabinofuranoside

Abstract Treatment of methyl 2,3-anhydro-α- d -lyxofuranoside with ammonium azide gave only crystalline methyl 3-azido-3-deoxy-α- d -arabinofuranoside (95%). Under analogous conditions, methyl 2,3-anhydro-5-O-p-tolylsulfonyl-α- d -lyxofuranoside gave only methyl 3,5-diazido-3,5-dideoxy-α- d -arabinofuranoside (84%), isolated as its crystalline 2-p-nitrobenzoate; methyl 2,3-anhydro-α- d -ribofuranoside gave methyl 2-azido-2-deoxy-α- d -arabinofuranoside and methyl 3-azido-3-deoxy-α- d -xylofuranoside (3:2; 85%); methyl 2,3-anhydro-5-O-p-tolylsulfonyl-α- d -ribofuranoside gave only methyl 2,5-diazido-2,5-dideoxy-α- d -arabinofuranoside (84%), isolated as its crystalline 3-p-nitrobenzoate; and methyl 2,3-anhydro-5-O-benzoyl-α- d -ribofuranoside gave predominantly methyl 2-azido-5-O-benzoyl-2-deoxy-α- d -arabino-furanoside, isolated as its crystalline 3-p-nitrobenzoate (85%). These findings are discussed on the basis of steric and electronic effects.

Synthesis of poly(acrylamide) copolymers containing 3,5-dideoxy-d-arabino-2-octulopyranosylonic acid (5-deoxy-Kdo) residues

Abstract The monosaccharides, sodium (allyl 3,5-dideoxy-α- and -β- d -arabino-2-octulopyranosid)onate, and the disaccharide, O-[sodium (3-deoxy-α- d -manno-2-octulopyranosyl)onate]-(2→4)-sodium (allyl 3,5-dideoxy-α- d -arabino-2-octulopyranosid)onate, corresponding to the 5-deoxy derivatives of Kdo-mono- and -di-saccharides, were synthesized via mercury(II) cyanide-promoted glycosylation of allyl alcohol or methyl (allyl 7,8-O-carbonyl-3,5-dideoxy-α- d -arabino-2-octulopyranosid)onate with Kdo or 5-deoxy-Kdo bromide derivatives, respectively. Removal of the protecting groups and subsequent copolymerization of the allyl glycosides with acrylamide gave artificial antigens suitable for the determination of epitope specificities displayed by monoclonal antibodies directed against the Kdo-region of enterobacterial lipopolysaccharides.

Synthesis of diamino acids - potential lipopolysaccharide antagonists

Abstract 1,4,6-Tri- O -acetyl-2,3-bis( tert -butyloxycarbonamido)-2,3,dideoxy-α- d -glucopyranose ( 8 ) was prepared through catalytic reduction and in situ tert -butyloxycorbonylation of 1,4,6-tri- O -acetyl-2-azido-2,3-dideoxy-3-nitro-α- d -glucopyranose ( 5 ). Starting from 8 , 4S,5S-bis(3R-hydroxytetradecanamido)octan-1,8-dioic acid ( 4 ) was synthesised in a series of steps.