Substrate specificity of fucosyl transferase III: An efficient synthesis of sialyl Lewisx-, sialyl Lewisa-derivatives and mimetics thereof

2000 ◽  
Vol 78 (6) ◽  
pp. 892-904 ◽  
Author(s):  
Beat Ernst ◽  
Bea Wagner ◽  
Gabi Baisch ◽  
Andreas Katopodis ◽  
Tammo Winkler ◽  
...  
Keyword(s):  
Substrate Specificity ◽  
Enzymatic Synthesis ◽  
Reaction Rates ◽  
Efficient Synthesis ◽  
Natural Substrate ◽  
Sialyl Lewisx ◽  
Sialyl Lewis ◽  
Sialyl Lewisa

Fucosyl transferase III (FucT III) has previously been characterized as the most general enzyme of the FucT family, as judged from its ability to catalyze the transfer of fucose to both Galβ(1-3)GlcNAc and Galβ(1-4)GlcNAc. In order to explore the synthetic potential of FucT III for the enzymatic synthesis of sialyl Lewisx and sialyl Lewisa derivatives, its substrate specificity has been probed using a number of natural substrate mimetics. A remarkable range of acceptor substrates was found when N-acetyl glucosamine was replaced by D-glucal, (R,R)-1,2-cyclohexanediol and (R,R)-butan-2,3-diol. Although the reaction rates were low compared to the reaction with the natural substrates, they proved to be sufficient for the synthesis of preparative amounts.Key words: fucosyl transferase III, sialyl Lewisa, sialyl Lewisx, carbohydrate mimetics.

Enzymatic Synthesis of Di-O-Phenylcarboxyl-ß-D-glucose Esters by an Acyltransferase from Oak Leaves

1990 ◽  
Vol 45 (1-2) ◽  
pp. 37-41 ◽  
Author(s):  
Georg G. Gross ◽  
Klaus Denzel
Keyword(s):  
Nmr Spectroscopy ◽  
Substrate Specificity ◽  
Enzymatic Synthesis ◽  
Quercus Robur ◽  
Reaction Rates ◽  
H Nmr ◽  
Anisic Acid ◽  
Oak Leaves

Leaves from oak (Quercus robur) contain an acyltransferase that catalyzes the conversion of β-glucogallin (1-O-galloyl-β-D-glucose) to 1,6-di-O-galloylglucose, an intermediate in the biosynthesis of gallotannins. Substrate specificity studies revealed th at this enzyme was also active with several structurally related 1-O-phenylcarboxyl-β-D-glucoses; appreciable reaction rates, however, were observed only in the form ation of 1,6-di-O-protocatechuoyl-β-D-glucose. This to date unknown ester, as well as its digalloyl analog, was synthesized using acyltransferase immobilized on phenyl-Sepharose, and characterized by UV and 1H NMR spectroscopy. In addition, the 1,2-di-O-β-D-glucose esters of benzoic and anisic acid were obtained in this investigation.

Chemo-enzymatic synthesis of trimeric sialyl Lewisx pentadecasaccharide

2002 ◽  
Vol 80 (6) ◽  
pp. 540-545 ◽  
Author(s):  
Yeuk Chuen Liu ◽  
Hong Li ◽  
Albin Otter ◽  
Vivekanand P Kamath ◽  
Markus B Streiff ◽  
...  
Keyword(s):  
Key Words ◽  
Enzymatic Synthesis ◽  
Sialyl Lewisx ◽  
Acetylneuraminic Acid ◽  
Sialyl Lewis

The enzymatic synthesis of trimeric sialyl Lewisx pentadecasaccharide (6), a 15-mer, from a trimannoside precursor required six different glycosyltransferase enzymes and four nucleotide donor sugars. Three N-acetylglucosaminyl residues were transferred from UDP-N-acetylglucosamine to a trimannoside by N-acetylglucosaminyltransferases I, II, and V, respectively. Galactosylation using β(1[Formula: see text]4) galactosyltransferase and UDP-galactose gave three N-acetyl lactosamine units in nonasaccharide 4. Sialylation of 4 with α(2[Formula: see text]3) sialyltransferase and CMP-N-acetylneuraminic acid was followed by fucosylation with α(1[Formula: see text]3) fucosyltransferase and GDP-fucose giving the 15-mer 6 in mg quantities. Compound 4 was also converted to a trimeric Lewisx dodecasaccharide 12-mer with α(1[Formula: see text]3) fucosyltransferase and GDP-fucose and to a trimeric α-2,6-sialyl N-acetyllactosamine dodecasaccharide 12-mer with α(2[Formula: see text]6) sialyltransferase and CMP-N-acetylneuraminic acid. Key words: glycosyltransferases, pentadecasaccharide, sialyl Lewisx.

Chemo-enzymatic Synthesis of 3′-azido/-amino-C-4′-spirooxetano-xylo nucleosides

2020 ◽  
Vol 7 (1) ◽  
pp. 120-127 ◽  
Author(s):  
Manish Kumar ◽  
Rajesh Kumar ◽  
Neha Rana ◽  
Ashok K. Prasad
Keyword(s):  
Substrate Specificity ◽  
Ethyl Acetate ◽  
Enzymatic Synthesis ◽  
Environmentally Friendly ◽  
Modified Nucleosides ◽  
Quantitative Yield ◽  
Hydroxymethyl Group ◽  
Crucial Step ◽  
X Ray ◽  
Sugar Derivative

Conformationally locked 3'-azido-C-4'-spirooxetano-xylonucleosides T, U, C and A have been synthesized by following chemo-enzymatic convergent route. One of the 3'-azido-C-4'- spirooxetano-xylonucleosides, i.e. T was converted into 3'-amino-C-4'-spirooxetano-xylothymidine by reduction of azide to amine with H2/Pd-C in ethyl acetate in quantitative yield. The crucial step in the synthesis of spirooxetano-xylonucleosides is the Lipozyme® TL IM-mediated exclusive diastereoselective acetylation of 4-C-hydroxymethyl group in dihydroxysugar derivative, 3-azido-3-deoxy-4-Chydroxymethyl- 1,2-O-isopropylidene-α-D-xylofuranose in quantitative yield. The diastereoselective monoacetylation of 4-C-hydroxymethyl in dihydroxysugar derivative was unambiguously confirmed by X-ray crystal study on the tosylated compound obtained by the tosylation of Lipozyme® TL IM - mediated monoacetylated sugar derivative. The broader substrate specificity and exclusive selective nature of Lipozyme® TL IM can be utilised for the development of environmentally friendly methodologies for the synthesis of different sugar-modified nucleosides of importance.

Chemical and enzymatic synthesis of glycocluster having seven sialyl lewis X arrays using β-cyclodextrin as a key scaffold material

Tetrahedron ◽  
2005 ◽  
Vol 61 (7) ◽  
pp. 1737-1742 ◽  
Author(s):  
Tetsuya Furuike ◽  
Reiko Sadamoto ◽  
Kenichi Niikura ◽  
Kenji Monde ◽  
Nobuo Sakairi ◽  
...  
Keyword(s):  
Enzymatic Synthesis ◽  
Sialyl Lewis X ◽  
Scaffold Material ◽  
Lewis X ◽  
Sialyl Lewis

Endothelial-selectin ligands sialyl Lewisx and sialyl Lewisa are differentiation antigens immunogenic in human melanoma

Cancer ◽  
1997 ◽  
Vol 79 (9) ◽  
pp. 1686-1697 ◽  
Author(s):  
Mepur H. Ravindranath ◽  
Amir A. Amiri ◽  
Philip M. Bauer ◽  
Mark C. Kelley ◽  
Richard Essner ◽  
...  
Keyword(s):  
Human Melanoma ◽  
Sialyl Lewisx ◽  
Differentiation Antigens ◽  
Selectin Ligands ◽  
Sialyl Lewisa

scholarly journals 2-Ketogluconate Kinase from Cupriavidus necator H16: Purification, Characterization, and Exploration of Its Substrate Specificity

Molecules ◽  
2019 ◽  
Vol 24 (13) ◽  
pp. 2393 ◽  
Author(s):  
Israel Sánchez-Moreno ◽  
Natalia Trachtmann ◽  
Sibel Ilhan ◽  
Virgil Hélaine ◽  
Marielle Lemaire ◽  
...  
Keyword(s):  
Substrate Specificity ◽  
Ralstonia Eutropha ◽  
Kinetic Constant ◽  
Cupriavidus Necator ◽  
Natural Substrate ◽  
Preparative Scale ◽  
Cupriavidus Necator H16 ◽  
Ralstonia Eutropha H16 ◽  
Chain Lengths ◽  
First Time

We have cloned, overexpressed, purified, and characterized a 2-ketogluconate kinase (2-dehydrogluconokinase, EC 2.7.1.13) from Cupriavidus necator (Ralstonia eutropha) H16. Exploration of its substrate specificity revealed that three ketoacids (2-keto-3-deoxy-d-gluconate, 2-keto-d-gulonate, and 2-keto-3-deoxy-d-gulonate) with structures close to the natural substrate (2-keto-d-gluconate) were successfully phosphorylated at an efficiency lower than or comparable to 2-ketogluconate, as depicted by the measured kinetic constant values. Eleven aldo and keto monosaccharides of different chain lengths and stereochemistries were also assayed but not found to be substrates. 2-ketogluconate-6-phosphate was synthesized at a preparative scale and was fully characterized for the first time.

Efficient Synthesis of Novel Quinolinone Derivatives via Catalyst-free Multicomponent Reaction

2020 ◽  
Vol 17 (5) ◽  
pp. 403-407
Author(s):  
Rui Du ◽  
Liangliang Han ◽  
Zhongqiang Zhou ◽  
Victor Borovkov
Keyword(s):  
Reaction Time ◽  
Multicomponent Reaction ◽  
Room Temperature ◽  
Reaction Rates ◽  
Solvent Free ◽  
Hydroxyl Group ◽  
Efficient Synthesis ◽  
Catalyst Free ◽  
Solvent Free Conditions ◽  
Substituted Benzaldehydes

The synthesis of 3-(aryl(piperidin-1-yl)methyl)-4-hydroxyquinolin-2(1H)-one derivatives via catalyst-free multicomponent reaction is described. The reaction of 4-hydroxyquinolin-2(1H)-one, piperidine, and 4-chlorobenzaldehyde was carried out in different solvents and under solvent-free conditions at room temperature. The best solvent in terms of the yield and reaction time was found to be dichloromethane. Most substituted benzaldehydes reacted with 4-hydroxyquinolin-2(1H)-one and piperidine to afford corresponding products in good-to-excellent yields. Aldehydes with electronwithdrawing groups were more reactive to exhibit higher reaction rates. However, 2-substituted benzaldehydes did not react with 4-hydroxyquinolin-2(1H)-one and piperidine under the reaction condition. Aldehydes bearing a hydroxyl group failed to produce the corresponding products.

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