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

Kanie, Osamu; Ohtsuka, Isao; Ako, Takuro; Daikoku, Shusaku; Kanie, Yoshimi; Kato, Rumiko

doi:10.1002/anie.200600433

Cited by 46 publications

(15 citation statements)

References 35 publications

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“…A 4‐aminobutyl glycoside ( 1 ) was found to generate a C‐ion species with a hemiacetal structure under CID conditions. Despite our previous finding on energy dependence in the dissociation of anomeric isomers, the dissociation of a pair of anomers of 4‐aminobutyl glycosides were indistinguishable 22–27. This suggested the dissociation mechanism is different from those of ordinary glycosides.…”

Section: Resultscontrasting

confidence: 62%

“…In such a case, an approach based on principal component analysis might be used, however, the source of information to be analyzed has been far from suitable and consists of limited structural isomers only 20, 21. For this reason, a combinatorial oligosaccharide library consisting of isomeric compounds with logical structural arrangements should provide indispensable information regarding structural characteristics 22–27. Energy‐resolved mass spectrometry (ERMS) has been used to address the energy dependence of structures of isomeric oligosaccharides where it was found that the lability of glycosides differs for anomeric configurations and linkage positions 28–34.…”

Section: Introductionmentioning

confidence: 99%

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Effect of induced magnetic field on peristaltic flow of a micropolar fluid in an asymmetric channel

Shit

Roy

2010

Numer Methods Biomed Eng

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Section: Resultscontrasting

confidence: 62%

Section: Introductionmentioning

confidence: 99%

Effect of induced magnetic field on peristaltic flow of a micropolar fluid in an asymmetric channel

Shit

Roy

2010

Numer Methods Biomed Eng

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“…A study by Kanie et al. gives a broad comparative picture, as the group synthesized a wide range of fucosyl–galactosyl oligosaccharides in both the solution and solid phase …”

Section: Glycosylationsmentioning

confidence: 99%

Chemical O‐Glycosylations: An Overview

2016

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The development of glycobiology relies on the sources of particular oligosaccharides in their purest forms. As the isolation of the oligosaccharide structures from natural sources is not a reliable option for providing samples with homogeneity, chemical means become pertinent. The growing demand for diverse oligosaccharide structures has prompted the advancement of chemical strategies to stitch sugar molecules with precise stereo‐ and regioselectivity through the formation of glycosidic bonds. This Review will focus on the key developments towards chemical O‐glycosylations in the current century. Synthesis of novel glycosyl donors and acceptors and their unique activation for successful glycosylation are discussed. This Review concludes with a summary of recent developments and comments on future prospects.

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“…The information accumulated, which is produced from a saccharide under analysis, is then compared with either the spectra or parameters obtained from CID experiments of product ions 27. Therefore, we are currently synthesizing an oligosaccharide library as the source of structural information 28–33…”

Section: Introductionmentioning

confidence: 99%

Anomeric information obtained from a series of synthetic trisaccharides using energy resolved mass spectra

et al. 2007

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The majority of structural investigations of oligosaccharides based on mass spectrometry use naturally occurring oligosaccharides, which do not allow extracting any common feature associated with anomeric structures and linkage positions. In order to address the issue to find such characteristics possibly contained in oligosaccharide structure, a synthetic combinatorial trisaccharide library was analyzed. The trisaccharides used in the analysis consisted of L-fucose, D-galactose and D-glucose, in which individual glycosidic linkages existed in either alpha- or beta-anomers. The analysis of energy-resolved mass spectra (ERMS) and the scattered plot analysis of some parameters obtained from ERMS for a series of trisaccharides revealed that lower activation energy was required for the dissociation of alpha-glycosides of these sugars compared to those of the corresponding beta-anomers. It is suggested that this finding may be useful in structural analysis of natural oligosaccharides.

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

Abstract: A dream team: Orthogonal glycosylation and solid‐phase synthesis were shown to be an excellent combination for polysaccharide synthesis (see scheme). The method was applied to generate a complete library of structural isomers with an L‐fucosyl‐D‐galactose sequence.

Cited by 46 publications

References 35 publications

Effect of induced magnetic field on peristaltic flow of a micropolar fluid in an asymmetric channel

Effect of induced magnetic field on peristaltic flow of a micropolar fluid in an asymmetric channel

Chemical O‐Glycosylations: An Overview

Anomeric information obtained from a series of synthetic trisaccharides using energy resolved mass spectra

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