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Search for "N-glycosides" in Full Text gives 8 result(s) in Beilstein Journal of Organic Chemistry.

N-Glycosides of indigo, indirubin, and isoindigo: blue, red, and yellow sugars and their cancerostatic activity

  • Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2840–2869, doi:10.3762/bjoc.20.240

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  • their activity against various types of cancer. N-Glycosides of indigo, indirubin, and isoindigo, blue, red, and yellow sugars, turned out to be of special interest because of their high cancerostatic activity and structural novelty. The present article provides an account on the synthesis and
  • anticancer activity of these compounds. Keywords: cancerostatic activity; carbohydrates; heterocycles; N-glycosides; indirubin; Introduction Indigo (1a), known for more than 6000 years and originally produced from indigo plants in India, represents a famous traditional blue pigment which was an expensive
  • [12][13]. In addition, there are more and more applications in the field of medicinal chemistry, especially for the treatment of cancer [14][15]. In the course of the renewed interest in the chemistry of indigo, indirubin, and isoindigo in the field of cancer research, N-glycosides of these compounds
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Published 08 Nov 2024

Anomeric modification of carbohydrates using the Mitsunobu reaction

  • Julia Hain,
  • Patrick Rollin,
  • Werner Klaffke and
  • Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1619–1636, doi:10.3762/bjoc.14.138

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  • achieve good results in the Mitsunobu procedure. We have reviewed on the one hand the literature on anomeric esterification, including glycosyl phosphates, and on the other hand glycoside synthesis, including S- and N-glycosides. The mechanistic details of the Mitsunobu reaction are discussed as well as
  • with simple alcohols (Scheme 20) [81][82]. In this case, of course, the sugar thioglycoside takes the role of the nucleophile rather than of the alcohol component in the Mitsunobu reaction. Reactions with NH acids to achieve N-glycosides Early on, phthalimide was regarded as a good Mitsunobu reagent
  • , owing to its NH acidity with a pKa of 8.3, thus offering the opportunity for the synthesis of N-glycosides of the N-glycosylimide type [83]. However, along with the formation of N-glycosylphthalimides, a side-reaction takes place, producing both glycosyl carbonates and N-glycosyl-1,2
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Published 29 Jun 2018

AuBr3-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars

  • Jayashree Rajput,
  • Srinivas Hotha and
  • Madhuri Vangala

Beilstein J. Org. Chem. 2018, 14, 682–687, doi:10.3762/bjoc.14.56

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  • -glycosylation albeit in low yields, thus indicating the possible utility of the oxophilic character of Au(III) towards the acetylated sugars. Among the N-glycosides, anomeric azido glycosides are important intermediates due to various applications in the synthesis of various glycosyl amides [28][29
  • purine and pyrimidine nucleoside synthesis using per-O-acyl/per-O-benzoyl furanosyl and pyranosyl o-hexynylbenzoates [23]. Subsequently, Hotha and co-workers utilized propargyl 1,2-orthoesters and alkynyl glycosyl carbonate donors for the synthesis of pyrimidine nucleosides [24][25]. In addition, N
  • -glycosides are also accessible by AuCl3/phenylacetylene-promoted Ferrier rearrangement of glycals [17], thus, demonstrating the efficient catalysis by alkynophilic and carbophilic Au complexes. Although the alkynophilicity and carbophilicity of Au complexes are well explored, very little is known about the
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Published 22 Mar 2018

Enzymatic synthesis of glycosides: from natural O- and N-glycosides to rare C- and S-glycosides

  • Jihen Ati,
  • Pierre Lafite and
  • Richard Daniellou

Beilstein J. Org. Chem. 2017, 13, 1857–1865, doi:10.3762/bjoc.13.180

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  • and GHs begin to be well understood by the glycoscientists. Their application to the enzymatic synthesis of a great variety of O- and N-glycosides are already becoming a routine. In addition the utilization of enzymes so to obtain rarer C- and S-analogues is an emerging field restricted to few
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Published 05 Sep 2017

Are D-manno-configured Amadori products ligands of the bacterial lectin FimH?

  • Tobias-Elias Gloe,
  • Insa Stamer,
  • Cornelia Hojnik,
  • Tanja M. Wrodnigg and
  • Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2015, 11, 1096–1104, doi:10.3762/bjoc.11.123

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  • potential as therapeutics and as tools for mechanistic studies in biology. This is because they are not sensitive towards enzymatic hydrolysis such as in physiological environment, in contrast to the naturally occurring O- and N-glycosides. With respect to our long-lasting interest in the design and
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Published 30 Jun 2015

Synthesis of 1,2-cis-2-C-branched aryl-C-glucosides via desulfurization of carbohydrate based hemithioacetals

  • Henok H. Kinfe,
  • Fanuel M. Mebrahtu,
  • Mandlenkosi M. Manana,
  • Kagiso Madumo and
  • Mokela S. Sokamisa

Beilstein J. Org. Chem. 2015, 11, 583–588, doi:10.3762/bjoc.11.64

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  • biologically important compounds. Although the synthesis of such carbohydrate derivatives is extensively studied, the synthesis of 1,2-cis-2-C-branched C-, S-, and N-glycosides is less explored. In this article a synthetic strategy for the synthesis of 1,2-cis-2-C-branched-aryl-C-glucosides is reported via a
  • -branched C-, S-, and N-glycosides is less explored [11]. Herein, we wish to report a stereoselective strategy for the synthesis of 1,2-cis-2-C-branched aryl-C-glucosides. Results and Discussion We recently reported on the stereoselective synthesis of carbohydrate based thiochroman 1 whereby the C-1 and C-2
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Published 29 Apr 2015

A new synthetic access to 2-N-(glycosyl)thiosemicarbazides from 3-N-(glycosyl)oxadiazolinethiones and the regioselectivity of the glycosylation of their oxadiazolinethione precursors

  • El Sayed H. El Ashry,
  • El Sayed H. El Tamany,
  • Mohy El Din Abdel Fattah,
  • Mohamed R. E. Aly,
  • Ahmed T. A. Boraei and
  • Axel Duerkop

Beilstein J. Org. Chem. 2013, 9, 135–146, doi:10.3762/bjoc.9.16

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  • , Germany 10.3762/bjoc.9.16 Abstract Glycosylations of 5-(1H-indol-2-yl)-1,3,4-oxadiazoline-2(3H)-thione delivered various degrees of S- and/or N-glycosides depending on the reaction conditions. S-Glycosides were obtained regiospecifically by grinding oxadiazolinethiones with acylated α-D-glycosyl halides
  • in basic alumina, whereas 3-N-(glycosyl)oxadiazolinethiones were selectively obtained by reaction with HgCl2 followed by heating the resultant chloromercuric salt with α-D-glycosyl halides in toluene under reflux. On using Et3N or K2CO3 as a base, mixtures of S- (major degree) and N-glycosides (minor
  • purification of mixtures of S- or N-glycosides to obtain the pure N-glycosides. The aminolysis of the respective S- or N-glycosides with ammonia in aqueous methanol served as further confirmation of their structures. While in S-glycosides the glycosyl moiety was cleaved off again, 3-N-(glycosyl
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Published 21 Jan 2013

The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates

  • Katharina Gallas,
  • Gerit Pototschnig,
  • Florian Adanitsch,
  • Arnold E. Stütz and
  • Tanja M. Wrodnigg

Beilstein J. Org. Chem. 2012, 8, 1619–1629, doi:10.3762/bjoc.8.185

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  • chemical stability towards physiological hydrolysis of the glycosidic linkage, compared to the naturally occurring O- as well as N-glycosides [26]. A broad application of this reaction is not feasible as yet. However, according to its mechanism, the scope of the Amadori rearrangement could well comprise a
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Published 25 Sep 2012
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