A strategy for chemical synthesis of selectively methyl-esterified oligomers of galacturonic acid

Clausen, Mads Hartvig; Jørgensen, Malene R.; Thorsen, Jesper; Madsen, Robert

doi:10.1039/b006981g

Cited by 52 publications

(19 citation statements)

References 26 publications

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“…25,26 This feature would make it possible to selectively deprotect first the 4-position and later on selectively cleave the C6-O-NAP. With this in mind, the two monosaccharide building blocks 6 27 and 7 28…”

Section: Resultsmentioning

confidence: 99%

Synthesis of branched and linear 1,4-linked galactan oligosaccharides

et al. 2018

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We report the synthesis of linear and branched (1→4)-d-galactans. Four tetrasaccharides and one pentasaccharide were accessed by adopting a procedure of regioselective ring opening of a 4,6-O-naphthylidene protecting group followed by glycosylation using phenyl thioglycoside donors. The binding of the linear pentasaccharide with galectin-3 is also investigated by the determination of a co-crystal structure. The binding of the (1→4)-linked galactan to Gal-3 highlights the oligosaccharides of pectic galactan, which is abundant in the human diet, as putative Gal-3 ligands.

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Section: Resultsmentioning

confidence: 99%

Synthesis of branched and linear 1,4-linked galactan oligosaccharides

et al. 2018

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“…In some experimentation to minimize the expenditure of DIBAL in this reaction we made the surprising and useful observation that 4 molecular sieves have a positive effect ( Table 1). Treatment of 6 with 0.1 m DIBAL at room temperature normally provided mainly monool ( [23] (Scheme 1). By similar methods 9 was converted to 11 in 84 % yield.…”

Section: Resultsmentioning

confidence: 99%

Artificial Glycosyl Phosphorylases

Rousseau

Ortega‐Caballero

Nordstrøm

et al. 2005

Chemistry A European J

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alpha- and beta-Cyclodextrin 6(A),6(D)-diacids (1 and 2), beta-cyclodextrin-6-monoacid (14), beta-cyclodextrin 6(A),6(D)-di-O-sulfate (16) and beta-cyclodextrin-6-heptasulfate (19) were synthesised. Acids 1, 2 and 14 were made from perbenzylated alpha- or beta-cyclodextrin, by diisobutylaluminum hydride (DIBAL)-promoted debenzylation, oxidation and deprotection. Addition of molecular sieves was found to improve the debenzylation reaction. Sulfates 16 and 19 were made by sulfation of the appropriately partially protected derivatives and deprotection. Catalysis of 4-nitrophenyl glycoside cleavage by these cyclodextrin derivatives was studied. Compounds 1, 2 and 16 were found to catalyse the reaction, with the catalysis following Michaelis-Menten kinetics and depending first order on the phosphate concentration. In a phosphate buffer (0.5 M, 59 degrees C, pH 8.0), K(M) varied from 2-10 mM and the k(cat)/k(uncat) ratio from 80-1000 depending on the stereochemistry of the substrate and the catalyst, with 2 being the best catalyst and with the sulfated 16 also displaying catalytic ability. The monoacid 14 and the heptasulfate 19 were not catalytic.

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“…To this end, diol 3 [4] was oxidised to diacid 5 in two steps, oxidation with Dess-Martin's reagent to the dialdehyde followed by chlorate oxidation, [7] with 86 % yield (Scheme 1). Scheme 1. This diacid was reacted with methallyl dichloride and cesium carbonate in DMF, affording smooth dialkylation resulting in diester 7 in 80 % yield.…”

Section: Resultsmentioning

confidence: 99%