A review of chemical methods for the selective sulfation and desulfation of polysaccharides

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

doi:10.1016/j.carbpol.2017.07.017

Cited by 100 publications

(73 citation statements)

References 121 publications

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“…Designed functionalized molecules by sulfation may find their application as novel non‐natural pharmaceutical agents. Hence, the instability of sulfated compounds under acidic pH and at high temperatures as well as lack of regioselectivity (C‐6 is the most reactive position and thus typically sulfated by conventional chemical methods) make the chemical synthesis challenging . In parallel, the synthetic importance of biocatalysts like sulfotransferases is currently growing, which work under mild conditions (moderate pH, low temperature, and low pressure).…”

Section: Discussionmentioning

confidence: 89%

“…In most of the applied chemical cellulose sulfation approaches, the regioselectivity is C‐6>C‐2>(≫) C‐3 . Regioselective sulfation at C‐3 is not commonly described in the literature, but it is possible for instance by using cellulose‐2,6‐trifluoroacetate in a SO 3 /pyridine/DMF system . Among the naturally obtainable GAGs, dermatan sulfate and chondroitin sulfate differ in their sulfation pattern depending on the individual sources .…”

Section: Introductionmentioning

confidence: 99%

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KnowVolution Campaign of an Aryl Sulfotransferase Increases Activity toward Cellobiose

Islam

Laaf

Infanzón

et al. 2018

Chemistry A European J

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Sulfated polysaccharides such as cellulose can mimic the functionalities of pathophysiologically important glycosaminoglycans. Enzymatic sulfation offers a green chemistry route to selective (mono)sulfation of oligosaccharides (e.g., cellobiose as a building block of cellulose) in aqueous solution, at ambient temperature, and high chemoselectivity. Here, we report the first KnowVolution campaign for the aryl sulfotransferase B (ASTB) from Desulfitobacterium hafniense to advance ASTB toward a synthetically attractive biocatalyst. The generated final recombination variant (ASTB-M5) carries two amino acid substitutions (Leu446Pro and Val579Lys) leading to an up to 7.6-fold increase in specific activity (6.15 U mg ) that was obtained with one round of KnowVolution. Mass spectrometry analysis confirmed a monosulfated product of cellobiose and structure elucidation by NMR confirmed the sulfation at the positions C-3 or C-4 of GlcNAc-linker-tBoc as opposed to the preferred C-6 by chemical means. Computational analysis suggested an important role of Leu446Pro in substrate-binding and recognized Val579Lys as a distal substitution.

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Section: Discussionmentioning

confidence: 89%

Section: Introductionmentioning

confidence: 99%

KnowVolution Campaign of an Aryl Sulfotransferase Increases Activity toward Cellobiose

Islam

Laaf

Infanzón

et al. 2018

Chemistry A European J

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“…To determine the position of the sulfate groups on the sugar rings of UP2-1, desulfation of the sulfated polysaccharide was performed according to the reference [14,28]. Briefly, UP2-1 (30 mg) was dissolved in water and passed through a 732 cation-exchange resin column (H + form), which was eluted with distilled water.…”

Section: Methodsmentioning

confidence: 99%

Structure and Bioactivity Screening of a Low Molecular Weight Ulvan from the Green Alga Ulothrix flacca

Wen

Sun

et al. 2018

Marine Drugs

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A water-soluble low molecular–weight polysaccharide named UP2-1 was isolated and purified from the marine green algae Ulothrix flacca using ion-exchange and size-exclusion chromatography. Composition and characteristics analyses showed that UP2-1 was a sulfated glucuronorhamnan consisting of rhamnose and glucuronic acid in a ratio of 2:1 with 21% sulfate content and a molecular weight of 5.0 kDa. Structural properties were determined using desulfation and methylation analyses combined with infrared spectrum (IR), gas chromatography-mass spectrometer (GC-MS) and nuclear magnetic resonance (NMR). The results showed that UP2-1 was a type of ulvan composed of alternate 4-linked-α-L-rhamnose residues (→4)-α-L-Rha(1→) and 4-linked-β-D-glucouronoc acid residues. The sulfate groups were mainly present in the O-3 position of →4)-α-L-Rha(1→. Most (70%) of the rhamnose was sulfated. UP2-1 also had a small amount of →4)-α-L-Rha(1→ branch at the O-2 position of the →4)-α-L-Rha(1→. UP2-1 exhibited significant anticoagulant and immunomodulating activity in vitro. This study demonstrated that the green algae Ulothrix flacca, which is used as a food and traditional marine herb in China, could also be considered as a source of bioactive ulvan.

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“…reviewed diverse methods to determine DSs, the molecular weights, and the position of sulfate . The synthetic methods to control the distribution of sulfate groups was reviewed in detail by Bedini et al …”

Section: Biomedical and Bioengineering Applications Of Artificially Smentioning

confidence: 99%

“…2.2.1. Applications in cell growth and differentiation : As a mimetic to overcome the limitations of heparin and heparan sulfate, CHS exhibits intrinsic biological properties towards cell differentiation, proliferation, and growth, according to the advances reported within the last decade …”

Section: Biomedical and Bioengineering Applications Of Artificially Smentioning

confidence: 99%

Recent Advances in Artificially Sulfated Polysaccharides for Applications in Cell Growth and Differentiation, Drug Delivery, and Tissue Engineering

2018

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Artificially sulfated polysaccharides, as the mimetics of native heparin and heparan sulfate, are important bioactive compounds, since they show great potential for tuning crucial biological activities within living organisms. Herein, we summarize progress in the development of artificially sulfated polysaccharides, such as cellulose sulfate, chitosan sulfate, and other sulfated polysaccharides, with a particular focus on the fields of biomedical and bioengineering applications in the past ten years. Their effects on cell growth and differentiation, but also as building blocks for drug carriers and medical implants, are emphasized.

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A review of chemical methods for the selective sulfation and desulfation of polysaccharides

Cited by 100 publications

References 121 publications

KnowVolution Campaign of an Aryl Sulfotransferase Increases Activity toward Cellobiose

KnowVolution Campaign of an Aryl Sulfotransferase Increases Activity toward Cellobiose

Structure and Bioactivity Screening of a Low Molecular Weight Ulvan from the Green Alga Ulothrix flacca

Recent Advances in Artificially Sulfated Polysaccharides for Applications in Cell Growth and Differentiation, Drug Delivery, and Tissue Engineering

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