From Polymer to Size‐Defined Oligomers: An Expeditious Route for the Preparation of Chondroitin Oligosaccharides

Lopin, Chrystel; Jacquinet, Jean‐Claude

doi:10.1002/anie.200503551

Cited by 65 publications

(59 citation statements)

References 26 publications

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“…For the synthesis of the heterogeneously 4-and 6-sulfated biotinylated tetrasaccharide derivatives, as discussed above, a fully acetylated and activated disaccharide derivative was required. The known disaccharide imidate 72, [7] easily prepared in seven steps from the natural polymer, fulfils these requirements (Scheme 7). The coupling reaction of imidate 72 with alcohols 23 and 24, as described above, gave the tetrasaccharide derivatives 73 (62 %) and 74 (67 %), respectively; the structures of which were evident from their 1 H NMR spectra.…”

Section: Synthesis Of the Homo-and Heterogeneously 4-and 6-sulfated Bmentioning

confidence: 82%

“…We previously reported a step-economical process for the chemical synthesis of size-defined chondroitin oligomers by semisynthesis starting from a commercially available natural CS polymer, [7] and the application of this strategy for the stereocontrolled construction of non-sulfated and biotinylated chondroitin oligomers, [8] as well as those of all known variants of CS. [9] Within a program devoted to the study of the biosynthetic pathways of CS chains in relation to osteoarthritis, we report herein an efficient and stereocontrolled construction of homo-and heterogeneously 4-and 6-sulfated chondroitin oligomers as their biotinylated conjugates, which are useful molecules as probes for studying the initiation of the polymerization of CS chains and the role of sulfotransferases involved in CS chain construction in cartilage.…”

Section: Introductionmentioning

confidence: 99%

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Efficient and Stereocontrolled Construction of Homo‐ and Heterogeneously 4‐ and 6‐Sulfated Biotinylated Chondroitin Oligomers

2011

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An efficient and stereocontrolled construction of homo‐ and heterogeneously 4‐ and 6‐sulfated biotinylated chondroitin oligomers has been investigated and is reported for the first time. This procedure allowed the preparation of oligomeric chondroitin derivatives with sulfate groups at specific positions; these should be useful probes for the study of the starting point of the polymerization reaction as well as the substrate specificity of sulfotransferases involved in the biosynthesis of chondroitin sulfate chains.

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Section: Synthesis Of the Homo-and Heterogeneously 4-and 6-sulfated Bmentioning

confidence: 82%

Section: Introductionmentioning

confidence: 99%

Efficient and Stereocontrolled Construction of Homo‐ and Heterogeneously 4‐ and 6‐Sulfated Biotinylated Chondroitin Oligomers

2011

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“…Sucrose octasulfate sodium salt was a gift from EUTICALS (Milano, Italy). Chondroitin sulfates were synthesized according to known procedures [4,24]. Carrageenans were prepared from various algae, as previously reported, and their structures were previously confirmed by spectroscopic analysis [25][26][27].…”

Section: Methodsmentioning

confidence: 99%

“…Furthermore, polysulfated carbohydrates are important biologically active molecules involved in many physiological and pathophysiological conditions. Glycosaminoglycans (GAGs), for example, are central players in blood coagulation, signal transduction, or cell-cell recognition [2][3][4]. Carrageenans, another important class of complex carbohydrates, are water-soluble linear sulfated galactans extracted from marine red algae, serving mainly as gelling or stabilizing agents in the food industry [5].…”

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confidence: 99%

Matrix-assisted laser desorption/ionization mass spectrometric analysis of polysulfated-derived oligosaccharides using pyrenemethylguanidine

Ohara

Jacquinet

Jouanneau

et al. 2009

J. Am. Soc. Mass Spectrom.

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A better understanding of the biological roles of carbohydrates requires the use of tools able to provide efficient and rapid structural information. Unfortunately, highly acidic oligomerssuch as polysulfated oligosaccharides-are very challenging to characterize because of their high polarity, structural diversity, and sulfate lability. These features pose special problems for matrix-assisted laser desorption/ionization mass spectrometric (MALDI-MS) analysis because polysulfated carbohydrates exhibit poor ionization efficiency and usually do not produce any signal. The present report demonstrates how MALDI-MS can be used to derive structural and compositional information from pure and mixed fractions of polysulfated oligosaccharides. Indeed, pyrenemethylguanidine (pmg, a derivatizing agent and ionization efficiency enhancer) was used for the analysis of di-to decasaccharides, carrying from two to nine sulfate groups. The method is applied to various highly sulfated chondroitin and carrageenan oligosaccharides as well as to the analysis of mixtures of compounds. In the mass spectra, the observation of a unique pmg-complexed ladder of peaks in both ionization modes allows an easy and rapid determination of both the number of sulfate groups carried by the analyte and its molecular weight. Moreover, we have developed a software tool for the rapid and automatic structural elucidation of carrageenans based on the mass spectra obtained. (J Am Soc Mass Spectrom 2009, 20, 131-137)

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“…Initial efforts in glycosynthesis, such as those by Lopin et al, demonstrated that chondroitin saccharides can be effectively synthesized in a highly convergent and efficient manner 6 . Gama et al 2 addressing the highly complex problems being generated in glyco-biology.…”

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confidence: 99%

Synthetic sugars enhance the functional glycomics toolkit

Turnbull

Linhardt

2006

Nat Chem Biol

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Glycosaminoglycan-protein interactions are an important frontier for discovering new mechanisms of cellular regulation by complex sugars. The integration of the 'chemical glycomics' strategies of synthetic chemistry, arrays and biological assays shows that the precise pattern of sugar sulfation dictates the specificity of a sugar's function.Understanding the complex functions of the glycome-the repertoire of sugars expressed by cells, tissues and organisms-is a substantial challenge in the postgenome era. Glycosaminoglycans (GAGs) are an important class of complex sugars whose structurally diverse polysaccharide chains contain large amounts of information 1 that is linked to an extensive range of biological functions. However, an understanding of the mode of glycan specificity underlying these functions has proven elusive 1 . A paper by Gama et al. published in this issue of Nature Chemical Biology reports the synthesis of a set of chondroitin sulfate (CS) tetrasaccharides whose interactions and bioactivity provide evidence for a 'sulfation code' in which recognition of selected proteins is conferred by specific sequences 2 . The use of a unique combination of synthetic chemistry, microarray technology and biological assays indicates a way forward for future studies aimed at understanding the selectivity and functions of GAG structures.Questions concerning the specificity of GAG-protein interactions abound and can only be definitively addressed using fully characterized compounds. The difficulty of obtaining such structures from nature is a significant bottleneck, and the development of tools and technologies to evaluate these molecules lags behind that of genomics and proteomics. Fortunately, the field is rapidly changing 3 . For instance, chemical synthesis avoids many of the purification problems that plague natural-products chemistry. In addition, large-scale interrogation of glycan-proteins is now possible, allowing the discovery of new molecular liaisons. In particular, recent studies describe new approaches for obtaining arrayed displays of both natural 4 and synthetic 5 GAG structures from the heparan sulfate-heparin family.Initial efforts in glycosynthesis, such as those by Lopin et al., demonstrated that chondroitin saccharides can be effectively synthesized in a highly convergent and efficient manner 6 . Gama et al. 2 extend these concepts by emphasizing the value of integrative science in NIH Public Access

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From Polymer to Size‐Defined Oligomers: An Expeditious Route for the Preparation of Chondroitin Oligosaccharides

Cited by 65 publications

References 26 publications

Efficient and Stereocontrolled Construction of Homo‐ and Heterogeneously 4‐ and 6‐Sulfated Biotinylated Chondroitin Oligomers

Efficient and Stereocontrolled Construction of Homo‐ and Heterogeneously 4‐ and 6‐Sulfated Biotinylated Chondroitin Oligomers

Matrix-assisted laser desorption/ionization mass spectrometric analysis of polysulfated-derived oligosaccharides using pyrenemethylguanidine

Synthetic sugars enhance the functional glycomics toolkit

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