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C-Glycosidic linkage

C-Glycosidic linkages are present in various natural products and may inhibit glycosidases due to the structural analogy to their O-counterparts.42 Glycosyl phosphates 63 and 48 served successfully in the a-selective synthesis of aryl... [Pg.124]

N. K. Kochetkov, N. N. Malysheva, E. M. Klimov, and A. V. Demchenko, Synthesis of polysaccharides with 1,2-c -glycosidic linkages by tritylthiocyanate polycondensation. Stereoregular a-(l-6)-D-glucan, Tetrahedron Lett., 33 (1992) 381-384. [Pg.27]

The C-glycosidic linkage is also found in many biologically important natural products such as marine natural toxins and antibiotics as shown in O Fig. 2. Since synthesis of these structurally complex natural products has been a major subject in modern organic synthesis, stere-... [Pg.756]

Naturally occurring compounds containing the C-glycosidic linkage... [Pg.758]

Stereoselective formation of the aryl-C-glycosidic linkage has been developed for synthesis of biologically important antibiotics and plant constituents. The most direct and widely used synthetic method is the Friedel-Crafts type reaction between electrophilic carbohydrate... [Pg.771]

Free radical reactions proceed under essentially neutral conditions that are compatible with various functional and protective groups used for saccharides. C-Glycosylation by means of radical reaction has been extensively developed [63]. This section will discuss intermolecular and intramolecular reactions for control of the stereochemistry of the C-glycoside linkage. [Pg.785]

Since transition metal-catalyzed C-C bond formations have been extensively studied, a number of reliable reactions with palladium or nickel catalysts have been reported for the synthesis of C-glycosidic linkages due to the high functional group compatibihty. [Pg.802]

In RNase 2 the main stmctural roles of the C-linked mannose seem to be to stabilize the IV-terminal loop of the protein and to keep Trp7 in a specific orientation, compared to the non-C-glycosylated form [3]. Site-directed mutagenesis has revealed that the sequence Trp-x-x-Trp is required for the C-mannosylation of the first tryptophan [4]. This C-glycosidic linkage has been proved to occur also in a number of other mammalian proteins, such as interleukin-12, complements, properdin, thrombospondin, erythropoietin receptor, mucins, and a bovine lens protein [5,6,7,8,9,10,11]. It has been demonstrated that the C-mannosylation is an enzyme-catalyzed event [12]. [Pg.2546]

C-Arylglycosides possess a stable C-C glycosidic linkage and exhibit a broad range of useful antitumor, antifungal and antibiotic properties. S.R. Pulley et al. developed a novel method for the synthesis of this important class of compounds by using the Dotz benzannuiation reaction between alkynyl glycosides and alkoxy phenyl chromium... [Pg.149]

This book is divided into eight chapters. Each of the first seven chapters centers around a different class of reactions. The sections within each chapter define subsets of the reaction classes. For example, Chapter 2 deals extensively with electrophilic substitutions as a means of forming C-glycosides. However, each section within the chapter deals with methods used for the formation or introduction of specific groups at the C-glycosidic linkage. [Pg.1]

Glycosylation is a reaction in which a sugar unit is covalently attached to the agly-cone through 0-, N-, S-, or C-glycosidic linkages. 0-glycosides are the most common ones. [Pg.46]

SF 2575 (Figure 3) have been isolated from Streptomyces species that have a C-glycosidic linkage at C9 and a salicyloyl ester at C4 (47,48). [Pg.664]

This result suggests that the immune system tolerates a deviation from the natural structure occurring on the tumour cell surface only in a narrow window. In the case of 64 neither the glycosyl tyrosine structure nor the C-glycosidic linkage and the (3-anomer configuration match the natural structure. [Pg.553]


See other pages where C-Glycosidic linkage is mentioned: [Pg.195]    [Pg.126]    [Pg.179]    [Pg.69]    [Pg.675]    [Pg.864]    [Pg.69]    [Pg.46]    [Pg.1581]    [Pg.165]    [Pg.67]    [Pg.94]    [Pg.49]    [Pg.1684]    [Pg.629]    [Pg.755]    [Pg.772]    [Pg.772]    [Pg.1797]    [Pg.2546]    [Pg.600]    [Pg.616]    [Pg.63]    [Pg.243]    [Pg.274]    [Pg.75]    [Pg.228]    [Pg.229]    [Pg.334]    [Pg.181]    [Pg.197]    [Pg.283]    [Pg.592]   
See also in sourсe #XX -- [ Pg.419 ]




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C-Glycosides

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Glycosides Glycosidic linkage

Glycosidic linkage

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