Specific and non-specific enzymes for furanosyl-containing conjugates: biosynthesis, metabolism, and chemo-enzymatic synthesis

Chlubnová, Ilona; Legentil, Laurent; Dureau, Rémy; Pennec, Alizé; Almendros, Mélanie; Daniellou, Richard; Nugier‐Chauvin, Caroline; Ferrières, Vincent

doi:10.1016/j.carres.2012.04.002

Cited by 37 publications

(31 citation statements)

References 225 publications

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“…[10] Observed PIF rearrangement has no analogy in organic chemistry and can be compared formally only with enzymatic isomerization of sugar nucleotides mediated by pyranose-furanose mutase (Scheme 1). [12] The discovered intriguing side process challenged us to study whether it can be performed in a straightforward way within the context of synthesizing oligosaccharides bearing furanoside units. Herewith we report our first results from this study.…”

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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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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“…The biosynthesis of Gal f has been studied in several laboratories in the past few years, and reviews on the subject have been published [7–8]. The main interest lies in the presence of Gal f in infectious microorganisms from bacteria to protozoa and in the fact that, being absent in mammals, the metabolism of Gal f is a good target for chemotherapy [9–11].…”

Section: Introductionmentioning

confidence: 99%

“…The main interest lies in the presence of Gal f in infectious microorganisms from bacteria to protozoa and in the fact that, being absent in mammals, the metabolism of Gal f is a good target for chemotherapy [9–11]. In particular, the unique UDP-galactopyranose mutase necessary for the production of the Gal f nucleotide has been thoroughly studied and characterized in several microorganisms producing β-galactofurans [7–8 10]. However, the enzymes involved in the metabolic incorporation of α-D-Gal f were not studied.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a derivative of α-D-Glcp(1->2)-D-Galf suitable for further glycosylation and of α-D-Glcp(1->2)-D-Gal, a disaccharide fragment obtained from varianose

Marino¹,

Lima²,

Mariño³

et al. 2012

Beilstein J. Org. Chem.

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SummaryThe presence of galactofuranoyl units in infectious microorganisms has prompted the study of the metabolic pathways involved in their incorporation in glycans. Although much progress has been made with respect to the biosynthesis of β-D-Galf-containing glycoconjugates, the mechanisms by which α-D-Galf units are incorporated remain unclear. Penicillium varians is a non-pathogenic fungus that produces varianose, a polysaccharide containing both α- and β-D-Galf units, which can be used as a model for biosynthetic studies on α-D-Galf incorporation. Synthetic oligosaccharide fragments related to varianose are useful as potential substrates or standards for characterization of the α-galactofuranosyl transferases. In this paper we report a straightforward procedure for the synthesis of α-D-Glcp(1→2)-D-Gal (1) and the use of this compound to monitor the natural disaccharide released from varianose by mild acid degradation. The synthesis, performed by the glycosylaldonolactone approach, involved a glucosylgalactofuranose derivative, suitable for the synthesis of higher oligosaccharides with an internal D-Galf.

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“…Although there are several studies reporting on the molecular mechanism of Gal f biosynthesis, there are only a few reports on Gal f metabolism (6). We previously identified a gene, termed ORF1110, encoding a Gal f -specific β- d -galactofuranosidase (Gal f -ase) (7, 8).…”

Section: Genome Announcementmentioning

confidence: 99%

Draft Genome Sequence of Streptomyces sp. JHA26, a Strain That Harbors a PA14 Domain Containing β- d -Galactofuranosidase

et al. 2017

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Specific and non-specific enzymes for furanosyl-containing conjugates: biosynthesis, metabolism, and chemo-enzymatic synthesis

Cited by 37 publications

References 225 publications

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

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

Synthesis of a derivative of α-D-Glcp(1->2)-D-Galf suitable for further glycosylation and of α-D-Glcp(1->2)-D-Gal, a disaccharide fragment obtained from varianose

Draft Genome Sequence of Streptomyces sp. JHA26, a Strain That Harbors a PA14 Domain Containing β- d -Galactofuranosidase

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