Herstellung von Oligosaccharid‐Bibliotheken durch Zufalls‐Glycosylierung

Abstract

hid 1994, 37. 297662080. Der Ester 7-[(ni-Azido-o-nitro)benzoyl]taxol wurde ebenfalls als Photoartinitdtsdnalogon genutzt: J. M. Carhoni. V. Farina, S.

Orthogonal Glycosylation Reactions on Solid Phase and Synthesis of a Library Consisting of a Complete Set of Fucosyl Galactose Isomers

“…[2][3][4][5][6][7][8][9][10] Current syntheses, however, can not be applied directly to the combinatorial chemistry of carbohydrates, for which the synthetic protocols must be extremely simple. [11] Various approaches to the creation of an oligosaccharide library have been described, [11][12][13][14] however, there are no reports of successful multiple glycosylation reactions that occur at every hydroxy-group position of a monosaccharide acceptor in a position-specific manner. We describe herein the synthesis of a complete disaccharide library with an l-fucosyl-dgalactose (Fuc-Gal) sequence with three parameters, namely, the anomeric configuration of the Fuc and Gal residues and the linkage position ( Table 1).…”

“…[20][21][22] In our strategy, the position of the interglycosidic linkage is fixed and the anomeric configuration is randomized to avoid formation of a highly complex mixture that would make isolation extremely difficult. [11] The glycosyl fluorides 17-20 were synthesized from the corresponding phenylthioglycosides of galactopyranose [23] by protection of a hydroxy group with a chloroacetyl group (ClAc), conversion of the phenylthio group into a fluoride substituent by treatment with N,Ndiethylaminosulfur trifluoride, and removal of the ClAc group. [24] The synthesis of a disaccharide library was carried out with 17-20, which contain orthogonal leaving groups, and a fucosyl donor in the form of the phenylthioglycoside 21 (Scheme 1).…”

Solid-Phase Supported Synthesis of the Branched Pentasaccharide Moiety That Occurs in Most Complex TypeN-Glycan Chains

“…The same cleavage reaction was used for RP-HPLC analysis of the products as described under Section C. The multifaceted structural and synthetic chemistry of carboranes continues to diversify after more than thirty years. [1,2] The reactions of various polyboranes with alkynes provides an access to a variety of carboranes; [1,3,4] however, with few exceptions, complex mixtures are obtained which may be difficult to separate. Transformations of simple organoboranes, [5,6] mainly to B-alkylated derivatives, promise more specific entries into carborane chemistry.…”

“…Varied glycan patterns are expressed in different types of tissues and at different stages of embryonic development. Consequently, for the chemical synthesis of these compounds [2] an approach is needed that intrisically permits a high degree of variation and the application of combinatorial [3] as well as split-synthesis techniques to supply a broad array of natural and problems. Even the use of the less symmetric MeCp anion as a ligand only yielded twinned crystals.…”

Orthogonal Glycosylation Reactions on Solid Phase and Synthesis of a Library Consisting of a Complete Set of Fucosyl Galactose Isomers

“…[1] Recent efforts directed toward the synthesis of complex glycoconjugates have made it possible to control the stereo-and regiospecificity of glycosylation reactions in solution-and solid-phase organic synthesis. [11] Various approaches to the creation of an oligosaccharide library have been described, [11][12][13][14] however, there are no reports of successful multiple glycosylation reactions that occur at every hydroxy-group position of a monosaccharide acceptor in a position-specific manner. [11] Various approaches to the creation of an oligosaccharide library have been described, [11][12][13][14] however, there are no reports of successful multiple glycosylation reactions that occur at every hydroxy-group position of a monosaccharide acceptor in a position-specific manner.…”