Synthetic 6-<i>O</i>-Methylglucose-Containing Polysaccharides (<i>s</i>MGPs):  Design and Synthesis

Meppen, Malte; Wang, Yonghui; Cheon, Hwan‐Sung; Kishi, Yoshito

doi:10.1021/jo061990v

Cited by 18 publications

(17 citation statements)

References 26 publications

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“…Since no single method is universally applicable and able to address all the issues associated with glycoside-bond formation, many other glycosyl donors, such as telluroglycosides, [130] glycosyl carbonates, [131] various heteroaryl glycosides, [15,[21][22][23][24][25]132] various N-substituted glycosyl carbamates, [133] methyl 3,5-dinitrosalicylate (DISAL) glycosides, [134,135] glycosyl disulfides, [136] glycosyl sulfimides, [137] N-glycosyl amides, [138] glycosyl phthalates, [139] 2-allyloxyphenyl glycosides, [140] glycosyl 5-hexynoates, [141] and propargyl glycosides [142] have also been devised in the past decade. Furthermore, the development of new activation systems for existing donors propels carbohydrate chemistry forward.…”

Section: Other Glycosyl Donors and Promotersmentioning

confidence: 99%

New Principles for Glycoside‐Bond Formation

2009

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Increased understanding of the important roles that oligosaccharides and glycoconjugates play in biological processes has led to a demand for significant amounts of these materials for biological, medicinal, and pharmacological studies. Therefore, tremendous effort has been made to develop new procedures for the synthesis of glycosides, whereby the main focus is often the formation of the glycosidic bonds. Accordingly, quite a few review articles have been published over the past few years on glycoside synthesis; however, most are confined to either a specific type of glycoside or a specific strategy for glycoside synthesis. In this Review, new principles for the formation of glycoside bonds are discussed. Developments, mainly in the last ten years, that have led to significant advances in oligosaccharide and glycoconjugate synthesis have been compiled and are evaluated.

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Section: Other Glycosyl Donors and Promotersmentioning

confidence: 99%

New Principles for Glycoside‐Bond Formation

2009

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“…(Li, et al, 2007c) Oligochitosan TOF Enzymatic hydrolysis of chitosan (Zhao, et al, 2007b) Oligomannans MALDI Regioselective synthesis of α-(3-6) and (Meppen, et al, 2007) Palayinose-containing oligosaccharides TOF Glucosyl transfer from β -D-Glc-1-PO 4 to palatinose with Thermo-anaerobacter brockii kojibiose phosphorylase. Pentasaccharide PI-88 MALDI One-pot glycosylations with catalytic activation (Valerio, et al, 2008) Penta-and hexa-saccharide derivatives TOF (CHCA) (β-D-Glcp-(1→6)) 4 and 5 -(1→4)-α-DManpOMe Phytoalexin-elicitor heptaglucoside TOF…”

Section: Maldi-ftms (No Matrix)mentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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This review is the fifth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2008. The first section of the review covers fundamental studies, fragmentation of carbohydrate ions, use of derivatives and new software developments for analysis of carbohydrate spectra. Among newer areas of method development are glycan arrays, MALDI imaging and the use of ion mobility spectrometry. The second section of the review discusses applications of MALDI MS to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, biopharmaceuticals, glycated proteins, glycolipids, glycosides and various other natural products. There is a short section on the use of MALDI mass spectrometry for the study of enzymes involved in glycan processing and a section on the use of MALDI MS to monitor products of the chemical synthesis of carbohydrates with emphasis on carbohydrate-protein complexes and glycodendrimers. Corresponding analyses by electrospray ionization now appear to outnumber those performed by MALDI and the amount of literature makes a comprehensive review on this technique impractical. However, most of the work relating to sample preparation and glycan synthesis is equally relevant to electrospray and, consequently, those proposing analyses by electrospray should also find material in this review of interest.

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“…Indeed, to date, only a handful of reports have addressed the chemical synthesis of PMPs or related analogues. [19][20][21][22][23] With regard to the MMPs, previous synthetic work has reported the preparation of analogues in which all of the mannopyranose moieties are methylated. [19] These compounds thus differ slightly from the natural glycans, in which the residue at the non-reducing terminus is unmethylated.…”

Section: Resultsmentioning

confidence: 99%

Carbohydrate–Lipid Interactions: Affinities of Methylmannose Polysaccharides for Lipids in Aqueous Solution

Liu¹,

Bai²,

Sun³

et al. 2012

Chemistry A European J

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The interactions between 3-O-methyl-mannose polysaccharides (MMPs), extracted from Mycobacterium smegmatis (consisting of a mixture of MMP-10, -11, -12 and -13) or obtained by chemical synthesis (MMP-5(s), -8(s), -11(s) and -14(s)), and linear saturated and unsaturated fatty acids (FAs), and a commercial mixture of naphthenic acids (NAs) in aqueous solution at 25 °C and pH 8.5 were quantified by electrospray ionization mass spectrometry (ESI-MS). Association constants (K(a)) for MMP binding to four FAs (myristic acid, palmitic acid, stearic acid and trans-parinaric acid) were measured by using an indirect ESI-MS assay, the "proxy protein" method. The K(a) values are in the 10(4)-10(5) M(-1) range and, based on results obtained for the binding of the synthetic MMPs with palmitic acid, increase with the size of the carbohydrate. Notably, the measured affinity of the extracted MMPs for trans-parinaric acid is two orders of magnitude smaller than the reported value, which was determined by using a fluorescence assay. Using a newly developed competitive binding assay, referred to as the "proxy protein/proxy ligand" ESI-MS method, it was shown that MMPs bind specifically to NAs in aqueous solution, with apparent affinities of approximately (5×10(4)) M(-1) for the mixture of NAs tested. This represents the first demonstration that MMPs can bind to hydrophobic species more complex than those containing linear alkyl/alkenyl chains. Moreover, the approach developed here represents a novel method for probing carbohydrate-lipid interactions.

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Synthetic 6-O-Methylglucose-Containing Polysaccharides (sMGPs): Design and Synthesis

Cited by 18 publications

References 26 publications

New Principles for Glycoside‐Bond Formation

New Principles for Glycoside‐Bond Formation

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Carbohydrate–Lipid Interactions: Affinities of Methylmannose Polysaccharides for Lipids in Aqueous Solution

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