5531-48-6Relevant academic research and scientific papers
Total synthesis of the Bacteroides fragilis zwitterionic polysaccharide a1 repeating unit
Pragani, Rajan,Seeberger, Peter H.
supporting information; experimental part, p. 102 - 107 (2011/03/17)
Nearly all bacteria capsular polysaccharides are T-cell-independent antigens that do not promote immunoglobulin class switching from IgM to IgG nor memory responses. In contrast, zwitterionic polysaccharides activate T-cell-dependent immune responses by m
Synthesis of the lipoteichoic acid of the Streptococcus species DSM 8747
Qiao, Yan,Lindner, Buko,Z?hringer, Ulrich,Truog, Peter,Schmidt, Richard R.
scheme or table, p. 3696 - 3702 (2010/08/03)
The lipoteichoic acid (LTA) of the Streptococcus species DSM 8747 consists of a β-d-galactofuranosyl diacylglycerol moiety (with different acyl groups) that is linked via 6-O to a poly(glycerophosphate) backbone; about 30% of the glycerophosphate moieties carry at 2-O hydrolytically labile d-alanyl residues. As typical LTA for this array of compounds LTA 1a was synthesized. To this end, from d-galactose the required galactofuranosyl building block 5 was obtained. The anomeric stereocontrol in the glycosylation step with 1,2-O-cyclohexylidene-sn-glycerol (4) was based on anchimeric assistance, thus finally leading to the unprotected core glycolipid 16. Regioselective protection and deprotection procedures permitted the defined attachment of the pentameric glycerophosphate 3 to the 6-hydroxy group of the galactose residue. Introduction of four d-alanyl residues led after global deprotection and purification to target molecule 1a possessing on average about two d-alanyl residues at 2-O of the pentameric glycerophosphate backbone, thus being in close accordance with the structure of the natural material.
Mild and efficient hydrolysis of thioglycosides to glycosyl hemiacetals using N-iodosaccharin
Mandal, Pintu Kumar,Misra, Anup Kumar
, p. 1207 - 1210 (2008/02/07)
A convenient methodology has been developed for the mild hydrolysis of thioglycosides to the corresponding hemiacetals using N-iodosaccharin without any requirement of co-activator. Most of the functional groups used for the protecting group manipulation of carbohydrates remain unaffected under the reaction conditions. Georg Thieme Verlag Stuttgart.
The first chemical synthesis of UDP[6-3H]-α-D- galactofuranose
Marino, Karina,Marino, Carla,Lima, Carlos,Baldoni, Luciana,De Lederkremer, Rosa M.
, p. 2958 - 2964 (2007/10/03)
Galactofuranose metabolism is a good target for the development of novel chemotherapeutic agents for the treatment of some microbial infections. This is a valid objective because galactofuranose is absent in mammals. Two enzymes are involved in the biosynthesis of molecules containing galactofuranose: a mutase, which catalyzes the interconversion of UDP-Galp and UDP-Galf, and D-galactofuranosyltransferases. The mechanism of action of the mutase and its inhibition is currently being investigated, whereas studies on the galactofuranosyltransferases have been hampered by the lack of a labeled galactofuranose nucleotide. In the present work we describe the chemical synthesis of UDP-α-D-[6-3H]Galf and we prove its effectiveness for incorporation of radioactive galactofuranose into a natural acceptor. This is the first report on the chemical synthesis of a labeled donor of galactofuranose with the potential for studying the galactofuranosyltransferases independently from the UDP-Galp mutase. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Studies of UDP-galactopyranose mutase from Escherichia coli: An unusual role of reduced FAD in its catalysis
Zhang, Qibo,Liu, Hung-Wen
, p. 9065 - 9070 (2007/10/03)
The galactofuranose moiety found in many surface constituents of microorganisms is derived from UDP-D-galactopyranose (UDP-Galp) via a unique ring contraction reaction catalyzed by UDP-Galp mutase. This enzyme, which has been isolated from several bacteri
Sulfur atom configuration of sulfinyl galactofuranosides determines different reactivities in glycosylation reactions
Ferrières, Vincent,Joutel, Jér?me,Boulch, Rachel,Roussel, Myriam,Toupet, Lo?c,Plusquellec, Daniel
, p. 5515 - 5519 (2007/10/03)
Sulfinyl β-D-galactofuranosides 3(R,S) and 9(R,S) were used as new hexofuranosyl donors in glycosylation reactions. Activation by trifluoromethanesulfonic anhydride involved different reaction pathways depending on the stereochemistry at the sulfur atom. Experimental results underlined a more suitable reactivity of 3(R) and 9(R) versus 3(S) and 9(S), respectively, for the synthesis of β-D-galactofuranosides. (C) 2000 Elsevier Science Ltd.
Synthesis of beta-D-Galf-(1-3)-D-GlcNAc by the trichloroacetamidate method and of beta-D-Galf-(1-6)-D-GlcNAc by SnCl4-promoted glycosylation.
Gallo-Rodriguez,Gandolfi,de Lederkremer
, p. 245 - 247 (2008/02/13)
In a continuation of our studies on the characterization of the glycoproteins of T. cruzi new galactofuranosyl disaccharides were synthesized. Beta-D-Galf-(1-3)-D-GlcNAc was prepared by employing the trichloroacetamidate procedure for the glycosylation st
