Novel Mechanism for Oxidative Cleavage of Glycosidic Bonds: Evidence for an Oxygen Dependent Reaction

Cui, Jian‐Fang; Bystroem, Styrbjoern E.; Eneroth, P.; Bjoerkhem, Ingemar

doi:10.1021/jo00105a050

Cited by 22 publications

(11 citation statements)

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“…These two aglycones can be readily prepared in a decagram scale from the extract of P. ginseng via degradation under basic conditions. [33,50] A collective synthesis of protopanaxatriol ginsenosides calls for full differentiation of the four hydroxyls on this tetraol. Thus, treatment of 56 with Ac 2 O in pyridine and sequential removal of the 12-O-acetyl group led to 12,20-diol 57.…”

Section: A Collective Synthesis Of Ginsenosides (35-38)mentioning

confidence: 99%

Synthesis of the Diverse Glycosides in Traditional Chinese Medicine

Zhu

2018

Chin. J. Chem.

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Traditional Chinese medicine (TCM) is a huge treasure trove for the discovery and development of modern pharmaceuticals. Indeed, numerous biologically and pharmacologically significant molecules have been identified from TCM; among them, a considerable portion belongs to glycosides. These glycosides are extremely diverse in structures, consisting of a large variety of aglycones, glycans, as well as glycosidic linkages. In addition, these glycosides occur frequently as a complicated mixture of congeners in the nature sources. This micro‐heterogeneity leads to the isolation of a homogeneous glycoside in an appreciable amount a formidable task. Therefore, development of synthetic approaches toward these nature glycosides has received great attention. In this account, we summarize our twenty‐year efforts spent on this topic. Fifty five representative TCM‐relevant glycosides synthesized by our group are highlighted. Based on the aglycone structure, these glycosides are categorized into three groups, i.e., steroid glycosides, triterpene glycosides, and flavonoid and phenolic glycosides. Typical synthetic approaches are discussed, showing the demanding tactics for regio‐ and stereo‐controlled installation of glycans and overall manipulation of protecting groups. These expedient and scalable synthetic approaches have provided practical alternatives to the accessibility of these TCM components and thus opportunities for their in depth biological and pharmacological studies.

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Section: A Collective Synthesis Of Ginsenosides (35-38)mentioning

confidence: 99%

Synthesis of the Diverse Glycosides in Traditional Chinese Medicine

Zhu

2018

Chin. J. Chem.

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“…3). Although this methodology does not allow to evaluate the complex pattern of ginsenosides, many interesting information have been obtained in these investigations [11][12][13][14]. Seventeen commercial ginseng preparations sold in Sweden were analysed for their content in ginsenosides.…”

Section: Gas Chromatography (Gc)mentioning

confidence: 99%

Analysis methods of ginsenosides

Fuzzati

2004

Journal of Chromatography B

230

121

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“…The former caused significant degradation and in one case resulted in the isolation of the monosaccharide 27 as the dominant product (71%). Cleavage of glycosidic bonds under basic conditions in the presence of atmospheric oxygen is known [ 29 , 30 ], and could account for the degradation seen here, but it is unclear why these disaccharides are so sensitive compared with the earlier series. Attempted sulfonation of the small amounts of available 26 produced also gave rise to complex mixtures from which the desired products could not be isolated.…”

Section: Resultsmentioning

confidence: 98%

Synthesis of Disaccharides Containing 6-Deoxy-a-L-talose as Potential Heparan Sulfate Mimetics

Fairweather¹,

Liu²,

Karoli³

et al. 2012

Molecules

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A 6-deoxy-α-L-talopyranoside acceptor was readily prepared from methyl α-L-rhamnopyranoside and glycosylated with thiogalactoside donors using NIS/TfOH as the promoter to give good yields of the desired α-linked disaccharide (69–90%). Glycosylation with a 2-azido-2-deoxy-D-glucosyl trichloroacetimidate donor was not completely stereoselective (α:β = 6:1), but the desired α-linked disaccharide could be isolated in good overall yield (60%) following conversion into its corresponding tribenzoate derivative. The disaccharides were designed to mimic the heparan sulfate (HS) disaccharide GlcN(2S,6S)-IdoA(2S). However, the intermediates readily derived from these disaccharides were not stable to the sulfonation/deacylation conditions required for their conversion into the target HS mimetics.

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Novel Mechanism for Oxidative Cleavage of Glycosidic Bonds: Evidence for an Oxygen Dependent Reaction

Abstract: In a previous work from our laboratory, an optimized procedure was worked out for cleavage of the glucosidic bonds in ginsenosides (Cui,

Cited by 22 publications

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Synthesis of the Diverse Glycosides in Traditional Chinese Medicine

Synthesis of the Diverse Glycosides in Traditional Chinese Medicine

Analysis methods of ginsenosides

Synthesis of Disaccharides Containing 6-Deoxy-a-L-talose as Potential Heparan Sulfate Mimetics

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