Synthesis of PI-88 analogue using novel O-glycosidation of exo-methylenesugars

Namme, Rie; Mitsugi, Takashi; Takahashi, Hideyo; Ikegami, Shiro

doi:10.1016/j.tetlet.2005.03.016

Cited by 24 publications

(8 citation statements)

References 13 publications

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“…Glycosylation occurs readily in plant cells, i.e., many kinds of secondary metabolites such as saponins and anthocyanins are produced in the form of glycosides in higher plants and most of them are accumulated in the vacuole of plant cells . Because one-step enzymatic glycosylation by cultured plant cells is useful for preparation of glycosides rather than chemical glycosylation which requires tedious steps (Mastelic et al, 2004;Namme et al, 2005), it has been the subject of increasing attention and has been carried out for many exogenous compounds, i.e., digitoxigenin, terpenoids, cineole, steviol, and tropic acid (Furuya et al, 1987b;Moyer and Gustine, 1987;Furuya et al, 1988;Tabata et al, 1988;Upmeier et al, 1988;Furuya et al, 1989;Ushiyama et al, 1989;Lewinson et al, 1996).…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of thymol, carvacrol, and eugenol by cultured cells of Eucalyptus perriniana

et al. 2006

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Section: Introductionmentioning

confidence: 99%

Biotransformation of thymol, carvacrol, and eugenol by cultured cells of Eucalyptus perriniana

et al. 2006

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“…The method was applied to the synthesis of a PI-88 analog (Scheme 20) [75]. PI-88 (98) is a phosphomannopentaose sulfate with good antiangiogenic activity and a potent inhibitor against heparanase.…”

Section: Application For C-glycoside Synthesismentioning

confidence: 99%

exo-Glycal Chemistry: General Aspects and Synthetic Applications for Biochemical Use

Lin¹,

Lin²,

Yang

2005

CTMC

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It is well known that carbohydrates play an indispensable role in a variety of essential biological activities, such as cell-cell adhesion, bacteria and virus infections, and tumor metastasis. Among an increasing number of sugars and sugar mimetics that have been designed and synthesized for the purpose of drug discovery, C-glycosides are considered to be one of the best choices on account of their stability and resemblance as they differ from normal glycosides only in glycosidic linkages. exo-Glycals are unsaturated sugars that have a double bond attached to the anomeric center outside the sugar ring. These carbohydrate molecules are useful for the synthesis of C-glycosides and compounds containing quaternary carbons, provided that the olefin can be properly reduced or functionalized. This review places special emphasis on two aspects of exo-glycals including general methods of preparation and synthetic applications for making biologically important molecules. The first half discusses the methods of addition/elimination and Ramburg-Bäcklund rearrangement that offer many beneficial features including a wide range of double bond substitutions, limited reaction steps, easy operation and good overall yields. The rest of the article demonstrates a number of synthetic studies using exo-glycals as the starting materials. The target molecules can be categorized into three groups, namely C-glycosides, enzyme inhibitors and bioactive natural products.

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“…It is of great use to study one-step enzymatic glycosylation by cultured plant cells in contrast to chemical glycosylation, which requires tedious steps and high cost [4,5]. Biotransformation is also considered economical, as the reaction is carried out without the need for expensive purified enzymes or UDP-sugars.…”

Section: Introductionmentioning

confidence: 99%

“…In this paper, we report the transgenic crown galls of P. quinquefolium as a novel biocatalyst to convert substrate 1 and 2 into their corresponding glycosides [paeonol-2-O-β-D-glucopyranoside (3) and emodin-6-O-β-D-glucopyranoside (5)]. Besides glycoside products, two other transformed products, one from methylation [1-(2,4-dimethoxyphenyl)-ethanone, 4] and another from hydroxylation [citreorosein (6)], were also obtained.…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of Paeonol and Emodin by Transgenic Crown Galls of Panax quinquefolium

L.¹,

Yan

Zhu³

et al. 2009

Appl Biochem Biotechnol

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Two aromatic substrates, paeonol (1) and emodin (2), were biotransformed by using transgenic crown galls of Panax quinquefolium. Four biotransformed products (3-6) were isolated and identified by physicochemical and spectral methods. A beta-glucoside (3, 73.2% of biotransformation yield) and a 1-(2,4-dimethoxyphenyl)- ethanone (4, 8.03%) were isolated from the suspension cultures after 7-day incubation of substrate 1. Upon administration of substrate 2, another beta-glucoside [emodin-6-O-beta-D: -glucopyranoside (5), 19.2%] and a hydroxylated derivative, citreorosein (6, 54.6%), were also obtained. The results demonstrate that transgenic crown galls of P. quinquefolium have the capacities to catalyze glycosylation, hydroxylation, and methylation reactions in the plant cells on those aromatic compounds.

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Synthesis of PI-88 analogue using novel O-glycosidation of exo-methylenesugars

Cited by 24 publications

References 13 publications

Biotransformation of thymol, carvacrol, and eugenol by cultured cells of Eucalyptus perriniana

Biotransformation of thymol, carvacrol, and eugenol by cultured cells of Eucalyptus perriniana

exo-Glycal Chemistry: General Aspects and Synthetic Applications for Biochemical Use

Biotransformation of Paeonol and Emodin by Transgenic Crown Galls of Panax quinquefolium

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