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Article ; Online: A review of chemical methods for the selective sulfation and desulfation of polysaccharides.

Bedini, Emiliano / Laezza, Antonio / Parrilli, Michelangelo / Iadonisi, Alfonso

2017 Volume 174, Page(s) 1224–1239

Abstract: Sulfated polysaccharides are known to possess several biological activities, with their sulfation pattern acting as a code able to transmit functional information. Due to their high biological and biomedical importance, in the last two decades many ... ...

Abstract	Sulfated polysaccharides are known to possess several biological activities, with their sulfation pattern acting as a code able to transmit functional information. Due to their high biological and biomedical importance, in the last two decades many reports on the chemical modification of their sulfate distribution as well as on the regioselective insertion of sulfate groups on non-sulfated polysaccharides appeared in literature. In this Review we have for the first time collected these reports together, categorizing them into three different classes: i) regioselective sulfation reactions, ii) regioselective desulfation reactions, iii) regioselective insertion of sulfate groups through multi-step strategies, and discussing their scope and limitations.
Language	English
Publishing date	2017-10-15
Publishing country	England
Document type	Journal Article ; Review
ZDB-ID	1501516-6
ISSN	1879-1344 ; 0144-8617
ISSN (online)	1879-1344
ISSN	0144-8617
DOI	10.1016/j.carbpol.2017.07.017
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Article ; Online: Exopolysaccharides from Marine and Marine Extremophilic Bacteria: Structures, Properties, Ecological Roles and Applications.

Casillo, Angela / Lanzetta, Rosa / Parrilli, Michelangelo / Corsaro, Maria Michela

Marine drugs

2018 Volume 16, Issue 2

Abstract: The marine environment is the largest aquatic ecosystem on Earth and it harbours microorganisms responsible for more than 50% of total biomass of prokaryotes in the world. All these microorganisms produce extracellular polymers that constitute a ... ...

Abstract	The marine environment is the largest aquatic ecosystem on Earth and it harbours microorganisms responsible for more than 50% of total biomass of prokaryotes in the world. All these microorganisms produce extracellular polymers that constitute a substantial part of the dissolved organic carbon, often in the form of exopolysaccharides (EPS). In addition, the production of these polymers is often correlated to the establishment of the biofilm growth mode, during which they are important matrix components. Their functions include adhesion and colonization of surfaces, protection of the bacterial cells and support for biochemical interactions between the bacteria and the surrounding environment. The aim of this review is to present a summary of the status of the research about the structures of exopolysaccharides from marine bacteria, including capsular, medium released and biofilm embedded polysaccharides. Moreover, ecological roles of these polymers, especially for those isolated from extreme ecological niches (deep-sea hydrothermal vents, polar regions, hypersaline ponds, etc.), are reported. Finally, relationships between the structure and the function of the exopolysaccharides are discussed.
MeSH term(s)	Bacteria/chemistry ; Biofilms/growth & development ; Ecology/methods ; Ecosystem ; Polymers/chemistry ; Polysaccharides, Bacterial/chemistry ; Seawater/microbiology
Chemical Substances	Polymers ; Polysaccharides, Bacterial
Language	English
Publishing date	2018-02-20
Publishing country	Switzerland
Document type	Journal Article ; Review
ZDB-ID	2175190-0
ISSN	1660-3397 ; 1660-3397
ISSN (online)	1660-3397
ISSN	1660-3397
DOI	10.3390/md16020069
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Article ; Online: Synthetic and semi-synthetic chondroitin sulfate oligosaccharides, polysaccharides, and glycomimetics.

Bedini, Emiliano / Parrilli, Michelangelo

Carbohydrate research

2012 Volume 356, Page(s) 75–85

Abstract: Chondroitin sulfate (CS) is a sulfated polysaccharide involved in a myriad of biological processes. Due to the variable sulfation pattern of CS polymer chains, the need to study in detail structure-activity relationships regarding CS biomedical features ... ...

Abstract	Chondroitin sulfate (CS) is a sulfated polysaccharide involved in a myriad of biological processes. Due to the variable sulfation pattern of CS polymer chains, the need to study in detail structure-activity relationships regarding CS biomedical features has provoked much interest in obtaining synthetic CS species. This paper reviews two decades of synthetic and semi-synthetic CS oligosaccharides, polysaccharides, and glycomimetics obtained by chemical, chemoenzymatic, enzymatic, and microbiological-chemical strategies.
MeSH term(s)	Biocatalysis ; Biomimetic Materials/chemical synthesis ; Biotinylation ; Carbohydrate Sequence ; Chondroitin Sulfates/biosynthesis ; Chondroitin Sulfates/chemical synthesis ; Combinatorial Chemistry Techniques ; Galactosamine/chemistry ; Glucose/chemistry ; Glucuronic Acid/chemistry ; Molecular Sequence Data ; Oligosaccharides/biosynthesis ; Oligosaccharides/chemical synthesis ; Small Molecule Libraries ; Structure-Activity Relationship ; Sulfates/chemistry
Chemical Substances	Oligosaccharides ; Small Molecule Libraries ; Sulfates ; Galactosamine (7535-00-4) ; Glucuronic Acid (8A5D83Q4RW) ; Chondroitin Sulfates (9007-28-7) ; Glucose (IY9XDZ35W2)
Language	English
Publishing date	2012-07-15
Publishing country	Netherlands
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Review
ZDB-ID	1435-7
ISSN	1873-426X ; 0008-6215
ISSN (online)	1873-426X
ISSN	0008-6215
DOI	10.1016/j.carres.2012.02.010
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Article: Versatile and self-assembling urea-linked neosaccharides from sugar aminoalcohols

Bedini, Emiliano / Cirillo, Luigi / Parrilli, Michelangelo

Tetrahedron. 2013 Jan. 28, v. 69, no. 4

2013

Abstract: The increasing interest in urea compounds as self-assembling molecules, ion transporters and organocatalysts prompted several efforts towards synthetic urea-linked glycomimetics. In this frame we studied in details a novel two steps dimerization reaction ...

Abstract	The increasing interest in urea compounds as self-assembling molecules, ion transporters and organocatalysts prompted several efforts towards synthetic urea-linked glycomimetics. In this frame we studied in details a novel two steps dimerization reaction of sugar vicinal aminoalcohol building blocks, opening a synthetic path to a series of urea-linked neosaccharides. Glucosamine neodisaccharide possessing an oxazolidinone–urea–oxazolidinone system could be transformed into both cyclic and higher linear neosaccharides. Furthermore, a series of six urea-linked glucosamine and galactosamine neodisaccharides was tested for self-assembling properties by measuring NMR spectra at different temperatures and concentrations as well as by gelation of several organic solvents.
Keywords	chemical structure ; dimerization ; galactosamine ; gelation ; glucosamine ; nuclear magnetic resonance spectroscopy ; solvents ; temperature ; transporters ; urea
Language	English
Dates of publication	2013-0128
Size	p. 1285-1296.
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	204285-x
ISSN	1464-5416 ; 0040-4020 ; 0563-2064
ISSN (online)	1464-5416
ISSN	0040-4020 ; 0563-2064
DOI	10.1016/j.tet.2012.12.005
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Article ; Online: Synthesis of the trisaccharide outer core fragment of Burkholderia cepacia pv. vietnamiensis lipooligosaccharide.

Bedini, Emiliano / Cirillo, Luigi / Parrilli, Michelangelo

Carbohydrate research

2012 Volume 349, Page(s) 24–32

Abstract: The synthesis of β-Gal-(1→3)-α-GalNAc-(1→3)-β-GalNAc allyl trisaccharide as the outer core fragment of Burkholderia cepacia pv. vietnamiensis lipooligosaccharide was accomplished through a concise, optimized, multi-step synthesis, having as key steps ... ...

Abstract	The synthesis of β-Gal-(1→3)-α-GalNAc-(1→3)-β-GalNAc allyl trisaccharide as the outer core fragment of Burkholderia cepacia pv. vietnamiensis lipooligosaccharide was accomplished through a concise, optimized, multi-step synthesis, having as key steps three glycosylations, that were in-depth studied performing them under several conditions. The target trisaccharide was designed with an allyl aglycone in order to open a future access to the conjugation with an immunogenic protein en route to the development of a synthetic neoglycoconjugate vaccine against this Burkholderia pathogen.
MeSH term(s)	Burkholderia cepacia/chemistry ; Carbohydrate Conformation ; Carbohydrate Sequence ; Lipopolysaccharides/chemistry ; Molecular Sequence Data ; Trisaccharides/chemical synthesis ; Trisaccharides/chemistry
Chemical Substances	Lipopolysaccharides ; Trisaccharides ; lipid-linked oligosaccharides
Language	English
Publishing date	2012-02-15
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	1435-7
ISSN	1873-426X ; 0008-6215
ISSN (online)	1873-426X
ISSN	0008-6215
DOI	10.1016/j.carres.2011.12.007
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Article ; Online: Inter vs. intraglycosidic acetal linkages control sulfation pattern in semi-synthetic chondroitin sulfate.

Laezza, Antonio / De Castro, Cristina / Parrilli, Michelangelo / Bedini, Emiliano

Carbohydrate polymers

2014 Volume 112, Page(s) 546–555

Abstract: Microbial-sourced unsulfated chondroitin could be converted into chondroitin sulfate (CS) polysaccharide by a multi-step strategy relying upon benzylidenation and acetylation reactions as key-steps for its regioselective protection. By conducting the two ...

Abstract	Microbial-sourced unsulfated chondroitin could be converted into chondroitin sulfate (CS) polysaccharide by a multi-step strategy relying upon benzylidenation and acetylation reactions as key-steps for its regioselective protection. By conducting the two reactions one- or two-pots, CSs with different sulfation patterns could be obtained at the end of the semi-synthesis. In particular, a CS polysaccharide possessing sulfate groups randomly distributed between positions 4 and 6 of N-acetyl-galactosamine (GalNAc) units could be obtained through the two-pots route, whereas the one-pot pathway allowed an additional sulfation at position 3 of some glucuronic acid (GlcA) units. This difference was ascribed to the stabilization of a labile interglycosidic benzylidene acetal involving positions O-3 and O-6 of some GlcA and GalNAc, respectively, when the benzylidene-acetylation reactions were conducted in a one-pot fashion. Isolation and characterization of a polysaccharide intermediate showing interglycosidic acetal moieties was accomplished.
MeSH term(s)	Acetals/chemistry ; Benzylidene Compounds/chemistry ; Chondroitin/chemistry ; Chondroitin Sulfates/chemical synthesis ; Chondroitin Sulfates/chemistry ; Glucuronic Acid/chemistry ; Magnetic Resonance Spectroscopy
Chemical Substances	Acetals ; Benzylidene Compounds ; Glucuronic Acid (8A5D83Q4RW) ; Chondroitin (9007-27-6) ; Chondroitin Sulfates (9007-28-7)
Language	English
Publishing date	2014-11-04
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1501516-6
ISSN	1879-1344 ; 0144-8617
ISSN (online)	1879-1344
ISSN	0144-8617
DOI	10.1016/j.carbpol.2014.05.085
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Article: Chemical Fucosylation of a Polysaccharide: A Semisynthetic Access to Fucosylated Chondroitin Sulfate

Laezza, Antonio / Iadonisi Alfonso / Castro Cristina De / De Rosa Mario / Schiraldi Chiara / Parrilli Michelangelo / Bedini Emiliano

Biomacromolecules. 2015 July 13, v. 16, no. 7

2015

Abstract: Chemical O-glycosylation of polysaccharides is an almost unexplored reaction. This is mainly due to the difficulties in derivatizing such complex biomacromolecules in a quantitative manner and with a fine control of the obtained structural parameters. In ...

Abstract	Chemical O-glycosylation of polysaccharides is an almost unexplored reaction. This is mainly due to the difficulties in derivatizing such complex biomacromolecules in a quantitative manner and with a fine control of the obtained structural parameters. In this work, chondroitin raw material from a microbial source was chemo- and regioselectively protected to give two polysaccharide intermediates, that acted in turn as glycosyl acceptors in fucosylation reactions. Further manipulations on the fucosylated polysaccharides, including multiple de-O-benzylation and sulfation, furnished for the first time nonanimal sourced fucosylated chondroitin sulfates (fCSs)âpolysaccharides obtained so far exclusively from sea cucumbers (Echinoidea, Holothuroidea) and showing several very interesting biological activities. A semisynthetic fCS was characterized from a structural point of view by means of 2D-NMR techniques, and preliminarily assayed in an anticoagulant test.
Keywords	Echinoidea ; Holothuroidea ; anticoagulants ; bioactive properties ; chondroitin sulfate ; nuclear magnetic resonance spectroscopy ; raw materials
Language	English
Dates of publication	2015-0713
Size	p. 2237-2245.
Publishing place	American Chemical Society
Document type	Article
ISSN	1526-4602
DOI	10.1021%2Facs.biomac.5b00640
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Article: A Route to Oligosaccharide-Appended Salicylaldehydes: Useful Building Blocks for the Synthesis of MetalâSalophen Complexes

Bedini, Emiliano / Forte Gianpiero / De Castro Cristina / Parrilli Michelangelo / Dalla Cort Antonella

Journal of organic chemistry. 2013 Aug. 16, v. 78, no. 16

2013

Abstract: A simple and general synthetic protocol to obtain oligosaccharide-appended salicylaldehydes, key intermediates for the synthesis of water-soluble metalâsalophen complexes, is here reported. Six new aldehydes have been prepared and fully characterized ... ...

Abstract	A simple and general synthetic protocol to obtain oligosaccharide-appended salicylaldehydes, key intermediates for the synthesis of water-soluble metalâsalophen complexes, is here reported. Six new aldehydes have been prepared and fully characterized as well as the corresponding zincâ and uranylâsalophen complexes. These new derivatives show very good solubility in water. Preliminary studies on the association of compound 19-U, that is, the uranyl maltotetraose derivative, with hydrogen phosphate and fluoride provide very encouraging results and open up the possibility of using such compounds for the efficient recognition of anions in pure water.
Keywords	aldehydes ; anions ; chemical reactions ; chemical structure ; fluorides ; hydrogen ; organic chemistry ; phosphates ; solubility
Language	English
Dates of publication	2013-0816
Size	p. 7962-7969.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021%2Fjo401148f
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Article ; Online: Conversion of yeast mannan polysaccharide in mannose oligosaccharides with a thiopropargyl linker at the pseudo-reducing end.

Marzaioli, Alberto M / Bedini, Emiliano / Lanzetta, Rosa / Parrilli, Michelangelo / De Castro, Cristina

Carbohydrate research

2014 Volume 383, Page(s) 43–49

Abstract: Polysaccharides are useful sources of preformed glycosyl linkages and therefore convenient building blocks can be prepared from them upon application of a proper degradation and derivatization scheme. Following this idea, the α-(1→6) linkages of this ... ...

Abstract	Polysaccharides are useful sources of preformed glycosyl linkages and therefore convenient building blocks can be prepared from them upon application of a proper degradation and derivatization scheme. Following this idea, the α-(1→6) linkages of this polysaccharide were broken applying acetolysis reaction and the pseudo-reducing position of the resulting acetylated mannose oligosaccharides was functionalized with a thiopropargyl appendage through thiourea activation of the related glycosyl iodides. Deacetylation of the final products and optimization of the purification procedures are discussed. The best yields were observed combining size exclusion chromatography and HPLC. Nine different oligosaccharides, from mono- to tetrasaccharides, mainly α-configured at the pseudo-reducing terminal, were obtained in pure form, presenting the propargyl appendage, a feature that makes them suitable substrates for successive functionalizations.
MeSH term(s)	Chromatography ; Chromatography, High Pressure Liquid ; Mannans/chemistry ; Mannose/chemistry ; Mannose/isolation & purification ; Oligosaccharides/chemistry ; Oligosaccharides/isolation & purification ; Polysaccharides/chemistry
Chemical Substances	Mannans ; Oligosaccharides ; Polysaccharides ; Mannose (PHA4727WTP)
Language	English
Publishing date	2014-01-13
Publishing country	Netherlands
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1435-7
ISSN	1873-426X ; 0008-6215
ISSN (online)	1873-426X
ISSN	0008-6215
DOI	10.1016/j.carres.2013.10.016
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Article ; Online: Structural investigation of the antagonist LPS from the cyanobacterium Oscillatoria planktothrix FP1.

Carillo, Sara / Pieretti, Giuseppina / Bedini, Emiliano / Parrilli, Michelangelo / Lanzetta, Rosa / Corsaro, Maria Michela

Carbohydrate research

2014 Volume 388, Page(s) 73–80

Abstract: Cyanobacteria are aquatic and photosynthetic microorganisms, which contribute up to 30% of the yearly oxygen production on the earth. They have the distinction of being the oldest known fossils, more than 3.5 billion years old, and are one of the largest ...

Abstract	Cyanobacteria are aquatic and photosynthetic microorganisms, which contribute up to 30% of the yearly oxygen production on the earth. They have the distinction of being the oldest known fossils, more than 3.5 billion years old, and are one of the largest and most important groups of bacteria on earth. Cyanobacteria are an emerging source of potentially pharmacologically active products and, among these, there are the lipopolysaccharides. Despite their significant and well documented activity, very little is known about the cyanobacteria lipopolysaccharides (LPS) structure. The aim of this work is to investigate the structure of the highly TLR4-antagonist lipopolysaccharide from the cyanobacterium Oscillatoria plankthotrix FP1. The LPS was purified and analysed by means of chemical analysis and 1H and 13C NMR spectroscopy. The LPS was then degraded by Smith degradation, HF and acetic acid hydrolyses. All the obtained products were investigated in detail by chemical analysis, NMR spectroscopy and by mass spectrometry. The LPS consists of a high molecular mass and very complex molecule lacking Kdo and heptose residues, where the polysaccharide chain is mainly constituted by a backbone of 3-substituted α-l-rhamnose units. The core region is rich in galacturonic acid and mannose residues. Moreover a glycolipid portion, similar to Gram-negative lipid A, was identified. This was built up of a non phosphorylated (1'→6) linked glucosamine disaccharide, acylated with 3-hydroxylated fatty acids. In particular 3-hydroxypentadecanoic and 3-hydroxyesadecanoic acids were found, together with esadecanoic and tetradecanoic ones. Finally the presence of a galacturonic acid residue at 6-position of the distal glucosamine in place of the Kdo residue is suggested.
MeSH term(s)	Acetic Acid ; Carbohydrate Sequence ; Disaccharides/analysis ; Fatty Acids/analysis ; Glucosamine/analysis ; Hexuronic Acids/analysis ; Hydrolysis ; Lipopolysaccharides/chemistry ; Lipopolysaccharides/isolation & purification ; Mannose/analysis ; Molecular Sequence Data ; Oscillatoria/chemistry ; Rhamnose/analysis
Chemical Substances	Disaccharides ; Fatty Acids ; Hexuronic Acids ; Lipopolysaccharides ; galacturonic acid (4JK6RN80GF) ; Glucosamine (N08U5BOQ1K) ; Mannose (PHA4727WTP) ; Acetic Acid (Q40Q9N063P) ; Rhamnose (QN34XC755A)
Language	English
Publishing date	2014-03-31
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	1435-7
ISSN	1873-426X ; 0008-6215
ISSN (online)	1873-426X
ISSN	0008-6215
DOI	10.1016/j.carres.2013.10.008
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