Proton and C-13 nuclear magnetic resonance spectra of some benzoylated aldohexoses

D’Accorso, Norma B.; Thiel, Inge M.E.; Schüller, Matthias

doi:10.1016/0008-6215(83)88453-5

Cited by 69 publications

(19 citation statements)

References 23 publications

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“…1 H And 13 C NMR characteristics given in this paper agreed well with similar values found in chemical literature for ß-D-galactofuranosic ring [21,22,[27][28][29][30][31][32] as well as of aglycone [33,34].…”

Section: Discussionsupporting

confidence: 78%

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Galactofuranosylated Galactocerebrosides, a New Drug Delivery System for Ceramides to Colon

Iga¹,

Iga²

2008

TOOCJ

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Section: Discussionsupporting

confidence: 78%

“…Penta-O-benzoyl-ß-D-galactofuranose was obtained by benzoylation of dry D-galactose in hot pyridine [21,22]. Tetra-O-benzoyl--D-galactofuranosyl bromide was prepared according to [23,24].…”

Section: Koenigs-knorr Synthesis Of Galactofuranosylated Galactocerebmentioning

confidence: 99%

Galactofuranosylated Galactocerebrosides, a New Drug Delivery System for Ceramides to Colon

Iga¹,

Iga²

2008

TOOCJ

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“…[3][4][5][6] Currently, the most widely used methods for furanoside synthesis are based on the initial transformation of unblocked monosaccharides by the Fischer reaction under kinetic control [7,8] or their high-temperature acylation. [7,9] All of these reactions proceed with the formation of a mixture of aand b-furanosides and are contaminated by re-spective pyranoside isomers that may require laborious chromatography in order to separate the target products. It is also notable that further regioselective introduction of O-blocking groups into furanosides can be more difficult than in the case of related pyranoside derivatives.…”

Section: Introductionmentioning

confidence: 99%

Pyranoside‐into‐Furanoside Rearrangement: New Reaction in Carbohydrate Chemistry and Its Application in Oligosaccharide Synthesis

Krylov

Argunov

Vinnitskiy

et al. 2014

Chemistry A European J

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Great interest in natural furanoside-containing compounds has challenged the development of preparative methods for their synthesis. Herein a novel reaction in carbohydrate chemistry, namely a pyranoside-into-furanoside (PIF) rearrangement permitting the transformation of selectively O-substituted pyranosides into the corresponding furanosides is reported. The discovered process includes acid-promoted sulfation accompanied by rearrangement of the pyranoside ring into a furanoside ring followed by solvolytic O-desulfation. This process, which has no analogy in organic chemistry, was shown to be a very useful tool for the synthesis of furanoside-containing complex oligosaccharides, which was demonstrated by synthesizing disaccharide derivatives α-D-Galp-(1→3)-β-D-Galf-OPr, 3-O-s-lactyl-β-D-Galf-(1→3)-β-D-Glcp-OPr, and α-L-Fucf-(1→4)-β-D-GlcpA-OPr related to polysaccharides from the bacteria Klebsiella pneumoniae and Enterococcus faecalis and the brown seaweed Chordaria flagelliformis.

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“…para-Nitrophenyl ␤-D-galactofuranoside (pNP-Gal f ) was chemically synthesized as described previously (18,40) or purchased (Toronto Research Chemicals, Toronto, Canada). 4-Methylumbelliferyl ␤-D-galactofuranoside (4MU-Gal f ) was chemically synthesized (41,42) as follows. 4-Methylumbelliferon (50.0 mmol) and BF 3 •Et 2 O (50.0 mmol) were added to a solution of perbenzoylated galactofuranose (10.0 mmol) with 4A molecular sieves in CH 3 CN (50 ml) at 0°C (41).…”

Section: Methodsmentioning

confidence: 99%

Biosynthesis of β-(1→5)-Galactofuranosyl Chains of Fungal-Type and O -Mannose-Type Galactomannans within the Invasive Pathogen Aspergillus fumigatus

Chihara

Tanaka

Izumi

et al. 2020

mSphere

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The pathogenic fungus Aspergillus fumigatus contains galactomannans localized on the surface layer of its cell walls, which are involved in various biological processes. Galactomannans comprise α-(1→2)-/α-(1→6)-mannan and β-(1→5)-/β-(1→6)-galactofuranosyl chains. We previously revealed that GfsA is a β-galactofuranoside β-(1→5)-galactofuranosyltransferase involved in the biosynthesis of β-(1→5)-galactofuranosyl chains. In this study, we clarified the biosynthesis of β-(1→5)-galactofuranosyl chains in A. fumigatus. Two paralogs exist within A. fumigatus: GfsB and GfsC. We show that GfsB and GfsC, in addition to GfsA, are β-galactofuranoside β-(1→5)-galactofuranosyltransferases by biochemical and genetic analyses. GfsA, GfsB, and GfsC can synthesize β-(1→5)-galactofuranosyl oligomers at up to lengths of 7, 3, and 5 galactofuranoses within an established in vitro highly efficient assay of galactofuranosyltransferase activity. Structural analyses of galactomannans extracted from ΔgfsB, ΔgfsC, ΔgfsAC, and ΔgfsABC strains revealed that GfsA and GfsC synthesized all β-(1→5)-galactofuranosyl residues of fungal-type and O-mannose-type galactomannans and that GfsB exhibited limited function in A. fumigatus. The loss of β-(1→5)-galactofuranosyl residues decreased the hyphal growth rate and conidium formation ability and increased the abnormal hyphal branching structure and cell surface hydrophobicity, but this loss is dispensable for sensitivity to antifungal agents and virulence toward immunocompromised mice. IMPORTANCE β-(1→5)-Galactofuranosyl residues are widely distributed in the subphylum Pezizomycotina of the phylum Ascomycota. Pezizomycotina includes many plant and animal pathogens. Although the structure of β-(1→5)-galactofuranosyl residues of galactomannans in filamentous fungi was discovered long ago, it remains unclear which enzyme is responsible for biosynthesis of this glycan. Fungal cell wall formation processes are complicated, and information concerning glycosyltransferases is essential for understanding them. In this study, we showed that GfsA and GfsC are responsible for the biosynthesis of all β-(1→5)-galactofuranosyl residues of fungal-type and O-mannose-type galactomannans. The data presented here indicate that β-(1→5)-galactofuranosyl residues are involved in cell growth, conidiation, polarity, and cell surface hydrophobicity. Our new understanding of β-(1→5)-galactofuranosyl residue biosynthesis provides important novel insights into the formation of the complex cell wall structure and the virulence of the members of the subphylum Pezizomycotina.

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Proton and C-13 nuclear magnetic resonance spectra of some benzoylated aldohexoses

Cited by 69 publications

References 23 publications

Galactofuranosylated Galactocerebrosides, a New Drug Delivery System for Ceramides to Colon

Galactofuranosylated Galactocerebrosides, a New Drug Delivery System for Ceramides to Colon

Pyranoside‐into‐Furanoside Rearrangement: New Reaction in Carbohydrate Chemistry and Its Application in Oligosaccharide Synthesis

Biosynthesis of β-(1→5)-Galactofuranosyl Chains of Fungal-Type and O -Mannose-Type Galactomannans within the Invasive Pathogen Aspergillus fumigatus

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