147072-52-4Relevant academic research and scientific papers
Synthesis of Cell-Permeable N-Acetylhexosamine 1-Phosphates
Capota, Emanuela,Kakde, Badrinath N.,Kohler, Jennifer J.,Tambar, Uttam K.
, p. 18257 - 18264 (2021/10/25)
We recently reported the incorporation of diazirine photo-cross-linkers onto the O-GlcNAc posttranslational modification in mammalian cells, enabling the identification of binding partners of O-GlcNAcylated proteins. Unfortunately, the syntheses of the diazirine-functionalized substrates have exhibited inconsistent yields. We report a robust and stereoselective synthesis of cell-permeable GlcNAc-1-phosphate esters based on the use of commercially available bis(diisopropylamino)chlorophosphine. We demonstrate this approach for two diazirine-containing GlcNAc analogues, and we report the cellular incorporation of these compounds into glycoconjugates to support photo-cross-linking applications.
Synthesis of modified peptidoglycan precursor analogues for the inhibition of glycosyltransferase
Dumbre, Shrinivas,Derouaux, Adeline,Lescrinier, Eveline,Piette, Andre,Joris, Bernard,Terrak, Mohammed,Herdewijn, Piet
, p. 9343 - 9351 (2012/07/14)
The peptidoglycan glycosyltransferases (GTs) are essential enzymes that catalyze the polymerization of glycan chains of the bacterial cell wall from lipid II and thus constitute a validated antibacterial target. Their enzymatic cavity is composed of a donor site for the growing glycan chain (where the inhibitor moenomycin binds) and an acceptor site for lipid II substrate. In order to find lead inhibitors able to fill this large active site, we have synthesized a series of substrate analogues of lipid I and lipid II with variations in the lipid, the pyrophosphate, and the peptide moieties and evaluated their biological effect on the GT activity of E. coli PBP1b and their antibacterial potential. We found several compounds able to inhibit the GT activity in vitro and cause growth defect in Bacillus subtilis. The more active was C16-phosphoglycerate-MurNAc-(l-Ala-d-Glu)-GlcNAc, which also showed antibacterial activity. These molecules are promising leads for the design of new antibacterial GT inhibitors.
Bacterial surface engineering utilizing glucosamine phosphate derivatives as cell wall precursor surrogates
Sadamoto, Reiko,Matsubayashi, Takeshi,Shimizu, Masataka,Ueda, Taichi,Koshida, Shuhei,Koda, Toshiaki,Nishimura, Shin-Ichiro
supporting information; experimental part, p. 10192 - 10195 (2009/11/30)
A study was conducted to examine glucosamine phosphate derivatives as cell wall precursor surrogates for bacterial surface display. N-acetylglu-cosamine-1- phosphate (GlcNAc-1-phosphate) derivate was used in the study as a bacterial cell wall precursor. It was observed during the study that the acetylation of the hydroxyl groups with high hydrophobicity can provide easy access to the cytoplasm of the bacteria. A flow cytometry was used to examine the incorporation of the derivatives into the bacterial cell wall. The study also used acetate buffer and biotin-PEO-hydrazide for washing the lactic acid bacteria. The incubation of lactic acid bacteria was carried out under the anaerobic conditions. This study can be used for development of oral vaccines.
A very simple synthesis of GlcNAc-α-pyrophosphoryl-decanol: A substrate for the assay of a bacterial galactosyltransferase
Brockhausen, Inka,Larsson, E. Andreas,Hindsgaul, Ole
, p. 804 - 807 (2008/09/18)
Lipid-linked sugar pyrophosphates, such as GlcNAc-pyrophosphoryl undecaprenol, are important intermediates in the biosynthesis of cell-surface bacterial polysaccharides. It was recently demonstrated that much simpler lipids could substitute for undecaprenol while retaining biological activity, thus making efficient synthetic access to this class of compounds highly desirable. In order to facilitate the synthesis of pure substrates for bacterial glycosyltransferases, we have developed a simple 'two-pot' synthesis which we demonstrate here for GlcNAc-α-pyrophosphoryl-decanol (4). GlcNAc pyrophosphate, produced by mild periodate oxidation/β-elimination of commercial UDP-GlcNAc, is alkylated using 1-iododecane to yield the target compound 4 in 39% yield. Compound 4 is shown to be an efficient acceptor for a bacterial galactosyltransferase.
Identification of a UDP-Gal: GlcNAc-R galactosyltransferase activity in Escherichia coli VW187
Montoya-Peleaz, Pedro J.,Riley, John G.,Szarek, Walter A.,Valvano, Miguel A.,Schutzbach, John S.,Brockhausen, Inka
, p. 1205 - 1211 (2007/10/03)
A novel acceptor substrate for galactosyltransferase was synthesized containing GlcNAcα-pyrophosphate, covalently bound to a hydrophobic phenoxyundecyl moiety (GlcNAc α-O-PO3-PO3-(CH 2)11-O-Phenyl). The new subs
Synthesis of P1-Citronellyl-P2-α-D-pyranosyl pyrophosphates as potential substrates for the E. coli undecaprenyl-pyrophosphoryl-N-acetylglucoseaminyl transferase MurG
Cudic, Predrag,Behenna, Douglas C.,Yu, Michael K.,Kruger, Ryan G.,Szewczuk, Lawrence M.,McCafferty, Dewey G.
, p. 3107 - 3110 (2007/10/03)
P1-Citronellyl-P2-α-D-pyranosyl pyrophosphates containing α-D-N-acetylglucoseaminyl, α-D-glucosyl, and α-D-N-acetylmuramyl carbohydrates were synthesized and used in substrate specificity studies of the Escherichia coli MurG enzyme. Oxalyl chloride activation of citronellyl phosphate for coupling to α-D-pyranose-1-phosphates resulted in markedly improved yields over traditional Khorana-Moffatt and diphenyl chlorophosphate activation strategies.
Synthesis and use of glycosyl phosphites: An effective route to glycosyl phosphates, sugar nucleotides, and glycosides
Sim, Mui Mui,Kondo, Hirosato,Wong, Chi-Huey
, p. 2260 - 2267 (2007/10/02)
An efficient and convenient synthetic route to glycosyl phosphites and phosphates has been developed that uses dibenzyl N,N-diethylphosphoramidite as a phosphitylating reagent. Glycosyl phosphites and phosphates of 2-acetamido-2-deoxy-D-galactose (GalNAc) (29), 2-acetamido-2-deoxy-D-glucose (GlcNAc) (30), D-galactose (Gal) (31), D-glucose (Glc) (32), D-mannose (Man) (33), L-rhamnose (Rha) (34), L-fucose (Fuc) (35), and N-acetylneuraminic acid (NeuAc) (41) were prepared by this procedure. Compounds 29 and 30 were obtained as α anomers exclusively, whereas compounds 31, 32, and 41 were obtained as β anomers, and compounds 33 and 34, as α anomers, predominately. The phosphates are useful for the synthesis of sugar nucleotides, and the phosphites are effective glycosylation reagents.
