Enzymatic Synthesis of Sialic Acids in Microfluidics to Overcome Cross-Inhibitions and Substrate Supply Limitations

2021 ◽  
Author(s):  
Franziska Obst ◽  
Michael Mertz ◽  
Philipp J. Mehner ◽  
Anthony Beck ◽  
Kathrin Castiglione ◽  
...  
Keyword(s):  
Enzymatic Synthesis ◽  
Sialic Acids ◽  
Substrate Supply

scholarly journals Sialic acids. Enzymatic synthesis of Tay-Sachs ganglioside.

1975 ◽  
Vol 250 (17) ◽  
pp. 6727-6734 ◽  
Author(s):  
J C Steigerwald ◽  
S Basu ◽  
B Kaufman ◽  
S Roseman
Keyword(s):  
Enzymatic Synthesis ◽  
Sialic Acids

scholarly journals ENZYMATIC SYNTHESIS OF CYTIDINE 5'-MONOPHOSPHO-SIALIC ACIDS

1962 ◽  
Vol 48 (3) ◽  
pp. 437-441 ◽  
Author(s):  
S. Roseman
Keyword(s):  
Enzymatic Synthesis ◽  
Sialic Acids

scholarly journals Enzymatic Synthesis of Trideuterated Sialosides

Molecules ◽  
2019 ◽  
Vol 24 (7) ◽  
pp. 1368 ◽  
Author(s):  
Zhi-P. Cai ◽  
Louis Conway ◽  
Ying Huang ◽  
Wen Wang ◽  
Pedro Laborda ◽  
...  
Keyword(s):  
Liquid Chromatography ◽  
Enzymatic Synthesis ◽  
Deuterium Oxide ◽  
Sialic Acids ◽  
Mass Spectrometric ◽  
Surface Proteins ◽  
Addition Reactions ◽  
Cell Surface Proteins ◽  
Internal Standards ◽  
Aldol Addition

Sialic acids are a family of acidic monosaccharides often found on the termini of cell surface proteins or lipid glycoconjugates of higher animals. Herein we describe the enzymatic synthesis of the two isotopically labeled sialic acid derivatives d3-X-Gal-α-2,3-Neu5Ac and d3-X-Gal-α-2,3-Neu5Gc. Using deuterium oxide as the reaction solvent, deuterium atoms could be successfully introduced during the enzymatic epimerization and aldol addition reactions when the sialosides were generated. NMR and mass spectrometric analyses confirmed that the resulting sialosides were indeed tri-deuterated. These compounds may be of interest as internal standards in liquid chromatography/mass spectrometric assays for biochemical or clinical studies of sialic acids. This was further exemplified by the use of this tri-deuterated sialosides as internal standards for the quantification of sialic acids in meat and egg samples.

Enzymatic Synthesis of Enantiomerically Pure Chiral Synthons: Lipase-Catalyzed Resolution of (R/S, 4E)-2-Methyl-4-hexen-l-ol

Synlett ◽  
1991 ◽  
Vol 1991 (04) ◽  
pp. 310-312
Author(s):  
Patrizia Ferraboschi ◽  
Daria Brembilla ◽  
Paride Grisenti ◽  
Enzo Santaniello
Keyword(s):  
Enzymatic Synthesis ◽  
Enantiomerically Pure

COMPARATIVE ACTION OF VARIOUS OESTROGENIC COMPOUNDS ON MOUSE VAGINAL SIALIC ACIDS (II)

1969 ◽  
Vol 62 (4) ◽  
pp. 663-670 ◽  
Author(s):  
Lars Carlborg
Keyword(s):  
Sialic Acid ◽  
Response Curve ◽  
Sialic Acids ◽  
Clear Cut ◽  
Suitable Parameter ◽  
Sufficient Degree ◽  
Comparative Action ◽  
Relative Potencies ◽  
Good Agreement

ABSTRACT Oestrogens administered in lower doses than necessary to induce full cornification of the mouse vagina induce mucification. It was shown previously that the degree of mucification could be estimated by quantitative determination of sialic acids. A suitable parameter for oestrogen assay was the measurement of vaginal sialic acid concentration which exhibited a clear cut dose response curve. Eleven assays of various oestrogens were performed with this method. Their estimated relative potencies were in good agreement with other routine oestrogen assays. A statistically sufficient degree of precision was found. The sensitivity was of the same order, or slightly higher, than the Allen-Doisy test.

Interspecific variation of zona pellucida glycoconjugates in several species of marsupial

Reproduction ◽  
2000 ◽  
pp. 111-120 ◽  
Author(s):  
JA Chapman ◽  
OW Wiebkin ◽  
WG Breed
Keyword(s):  
Glycine Max ◽  
Sialic Acid ◽  
Zona Pellucida ◽  
Fluorescein Isothiocyanate ◽  
Interspecific Variation ◽  
Lectin Histochemistry ◽  
Sialic Acids ◽  
Arachis Hypogea ◽  
Marsupial Species ◽  
Similar Intensity

The zona pellucida glycoconjugate content of several marsupial species was investigated using differential lectin histochemistry. Ovaries from fat-tailed dunnarts, a southern brown bandicoot, grey short-tailed opossums, brushtail possums, ringtail possums, koalas and eastern grey kangaroos were fixed, embedded in paraffin wax, sectioned and stained with ten fluorescein isothiocyanate-conjugated lectins. Sections were also incubated with either neuraminidase or saponified, respectively, before incubation with the lectins to identify saccharide residues masked by sialic acids or O-acetyl groups on sialic acids. The zonae pellucidae surrounding the oocytes of the marsupials demonstrated interspecific variation in glycoconjugate content, with mannose-containing glycoconjugates exhibiting the greatest variation. Some of the zona pellucida glycoconjugates of all species, except those of the opossums, were masked by sialic acid with an increase in fluorescence with lectins from Arachis hypogea (PNA), and Glycine max (SBA), after desialylation. The disaccharide beta-galactose(1-4)N-acetyl-D-glucosamine appeared to be conformationally masked by O-acetyl groups of sialic acids in the zonae pellucidae of all species, with an increase in fluorescence with the lectin from Erythrina cristagalli (ECA), after saponification. Similar intensity and localization of beta-(1-4)-N-acetyl-D-glucosamine, as shown by staining of the lectin from Triticum vulgaris (WGA), to the inner and outer regions of the zona pellucida, were found to those reported in eutherian species. WGA fluorescence became uniform throughout the zonae pellucidae after saponification, indicating differential O-acetylation of sialic acids on the internal compartment of the zonae pellucidae.

Human Neuraminidases Have Reduced Activity Towards Modified Sialic Acids on Glycoproteins

2020 ◽  
Author(s):  
Carmanah D. Hunter ◽  
Elizabeth Porter ◽  
Christopher Cairo
Keyword(s):  
Substrate Specificity ◽  
General Trend ◽  
Sialic Acids ◽  
Enzyme Specificity ◽  
Naturally Occurring ◽  
Bovine Submaxillary Mucin ◽  
Reduced Activity

This work investigated the substrate specificity of hNEU enzymes for a glycoprotein substrate (bovine submaxillary mucin) containing 9-<i>O</i>-acetylated and Neu5Gc residues. Using this model substrate, we observe a general trend for hNEU tolerance of Neu5Ac>Neu5Gc>>>Neu5,9Ac<sub>2</sub>, consistent with our previous results with glycolipid substrates. These results expand our understanding of hNEU enzyme specificity and suggest that naturally occurring modifications of sialic acids can play a role in regulating hNEU activity.

A common precursor to both prebiotic and biological pathways to RNA nucleotides

2018 ◽  
Author(s):  
Andrea Pérez-Villa ◽  
Thomas Georgelin ◽  
Jean-François Lambert ◽  
Marie-Christine Maurel ◽  
François Guyot ◽  
...  
Keyword(s):  
Enzymatic Synthesis ◽  
De Novo ◽  
Life Forms ◽  
Hydrothermal Conditions ◽  
Modern Life ◽  
Ab Initio Simulations ◽  
Spontaneous Formation ◽  
Common Precursor ◽  
Open Issue ◽  
Anomeric Carbon

Understanding the mechanism of spontaneous formation of ribonucleotides under realistic prebiotic conditions is a key open issue of origins-of-life research. In cells, <i>de novo</i> and salvage nucleotide enzymatic synthesis combines 5-phospho-α -D-ribose-1-diphosphate ( α-PRPP) and nucleobases. Interestingly, these reactants are also known as prebiotically plausible compounds. Combining ab initio simulations with mass spectrometry experiments, we compellingly demonstrate that nucleobases and α -PRPP spontaneously combine, through the same facile mechanism, forming both purine and pyrimidine ribonucleotides, under mild hydrothermal conditions. Surprisingly, this mechanism is very similar to the biological one, and yields ribonucleotides with the same anomeric carbon chirality as in biological systems. These results suggest that natural selection might have optimized – through enzymes – a pre-existing ribonucleotide formation mechanism, carrying it forward to modern life forms.

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