This Article Full Text (PDF) References Alert me when this article is cited Alert me if a correction is posted Services Email this article to a friend Similar articles in this journal Alert me to new issues of the journal Add to Saved Citations Download to citation manager Request Permissions Request Reprints Add to My Marked Citations Citing Articles Citing Articles via Google Scholar Citing Articles via Scopus Google Scholar Articles by Sekljic, H. Articles by Brade, H. Search for Related Content PubMed Articles by Sekljic, H. Articles by Brade, H. Social Bookmarking                         What's this?

Synthesis of neoglycoproteins containing 5-O-phosphorylated Kdomonosaccharide, 4-O- and 5-O-phosphorylated -Kd(2 6)-2-acetamido-2-deoxy- -D-glucopyranosyl disaccharide residues

Department of Chemistry, University of Agriculture, Vienna, Austria

Paul Kosma

Department of Chemistry, University of Agriculture, Vienna, Austria

Johannes Bartek

Department of Chemistry, University of Agriculture, Vienna, Austria

Koichi Fukase

Department of Chemistry, Osaka University, Osaka, Japan

Shoichi Kusumoto

Department of Chemistry, Osaka University, Osaka, Japan

Helmut Brade

Research Center Borstel, Borstel, Germany

Radical addition of cysteamine to anomeric allyl glycosides of Kdo 5-phosphates 1 and 4 afforded good yields of the corresponding 3-(2-aminoethylthio)propyl glycosides. Similar reactions with the -allyl glycoside of Kdo 4-phosphate 7 led to substantial formation of the dephosphorylated product 10 through intramolecular hydrolysis of the 4-O-phosphomonoester by the terminal amino function of the spacer group. Similar side reactions occurred upon deblocking of the 4-O-phosphorylated 6-aminohexyl--glycoside lactone derivative 18. Allyl glycosides of 4'- O- and 5'-O-phosphorylated Kd (2 6)-glucosamine derivatives were prepared in good yields via phosphorylation using the amidite procedure. The 4'-phosphate moiety was introduced following intramolecular protection of the 5'-OH group as a lactone. Subsequent deprotection gave the allyl glycosides 25 and 33 which were transformed into the corresponding stable spacer derivatives 26 and 34 by coupling with cysteamine. The ligands were activated with thiophosgene and reacted with bovine serum albumin to give the neoglycoconjugates 3, 6, 27 and 35 to be used in immunochemical studies of monoclonal antibodies directed against Haemophilus influenzae Re-mutant and related lipopolysaccharides.

Journal of Endotoxin Research, Vol. 3, No. 2, 151-164 (1996)
DOI: 10.1177/096805199600300208


CiteULike    Complore    Connotea    Del.icio.us    Digg    Reddit    Technorati    Twitter    What's this?