A Method of Orthogonal Oligosaccharide Synthesis Leading to a Combinatorial Library Based on Stationary Solid‐Phase Reaction

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

doi:10.1002/asia.200600210

Cited by 30 publications

(26 citation statements)

References 106 publications

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“…Synthesized trisaccharides were used in the experiments 33. Synthesis was achieved on a small scale, based on solid‐phase reactions, where stereoselectivity was not controlled, in order to obtain all anomers in one sequence of reaction.…”

Section: Methodsmentioning

confidence: 99%

“…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%

“…The importance of the ERMS has been recognized and it is applied to investigate the structures of ions and noncovalently associated ions 34–43. Based on our results that ERMS can be analyzed quantitatively,22 we applied the method to a series of trisaccharides consisting of all possible combinations of anomers,33 and describe herein a quantitative analysis of CID spectra, especially energy‐resolved spectra and the relationship between an anomeric configuration and some parameters related to the dissociation energies of individual glycosidic linkages.…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2007

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“…Furthermore, drug discovery based on the identified pharmacophore seems more promising [34,35]. The importance of utilizing combinatorial library is also recognized in the glycan research field, which is still extremely challenging [27][28][29]31,32,34,[36][37][38][39][40][41][42][43][44][45][46][47][48][49][50].…”

Section: Review Chemical Aspects Of Glycan Structurementioning

confidence: 99%

Addressing the glycan complexity by using mass spectrometry: In the pursuit of decoding glycologic

Kanie¹,

Kanie²

2017

Bio Chem Comp

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Biomolecules often contain carbohydrates. Such molecules, namely glycoconjugates, play central roles in cell adhesion, tumor migration, and attachment of pathogens. The conjugation of "natural products" with glycans is not a template-dependent process but is achieved by multiple enzymatic reactions. Because of the nature of the synthetic process, glycans exist as a complex mixture creating a glycoform and thus, the analysis becomes inevitably difficult. Mass spectrometry is one of the most informative, and thus important, tools for the structural analysis of glycans. The obvious advantage of mass spectrometry is the high sensitivity at low femtomole detection levels. A variety of ions can be obtained depending on the adducted cationic species. In order to obtain sequential information, the gas-phase dissociation reaction is used. Among the various techniques, collision-induced dissociation (CID) has been frequently used in the past. Although the technique is proven useful, there are cases that normal CID process is not suitable. This review highlights an emerging technique that focuses on the activation-energy difference between the isomeric glycans, and will complement the current methods. Furthermore, the possible source and the methodology for obtaining useful structural information are discussed.

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“…By screening the library prepared in this combinatorial fashion against a flower lectin, they discovered new carbohydrate ligands with a higher affinity to the protein than the natural ligand 13. On the other hand, a straightforward oligosaccharide library synthesis was reported by Kanie, et al, which involves an orthogonal glycosylation method on a polymeric support 14. These methods use the solid-phase technique which presents several limitations such as decreased glycosylation reaction rates compared to solution methods and incomplete coupling.…”

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confidence: 99%

Use of ionically tagged glycosyl donors in the synthesis of oligosaccharide libraries

Kim

Gray

2009

Bioorganic & Medicinal Chemistry Letters

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Oligosaccharides are thought to play essential roles in coding for the vast amount of information required in various biological recognition processes. For example, inside a cell, oligosaccharides promote the folding of proteins 1 and O-GlcNAc modification of nuclearcytoplasmic proteins initiates a dynamic signaling mechanism in concert with phosphoryation 2 . On the cell surface, they are the key surface molecules that communicate with neighboring molecules, constituting a dense information storage system. 3 This 'carbohydrate code' serves as recognition elements and thus also induces immunological responses to both bacterial and viral infections. 4,5 Abnormalities in oligosaccharide display are closely associated with several human diseases such as immune dysfunction6 and cancer 7 . Therefore, gaining insight into how carbohydrates function as recognition signals, and developing efficient ways to prevent undesirable interactions between carbohydrates and their protein signals are very important. Toward this end, the synthesis of oligosaccharides and the screening of their biological activities are often the first steps to be accomplished. However, the discrete synthesis and biological screening of individual oligosaccharides is extremely laborious. While combinatorial chemistry is well suited to the generation of a large number of chemicals (libraries) in a short time and has already seen successful application to the preparation of peptides, 8 oligonucleotides,9 and small organic molecules, 10 the application of such technology to the synthesis of oligosaccharide libraries is much more challenging due to the inherent chemical complexity of carbohydrates.Spurred by the recent explosion of interest in glycobiology, tremendous progress has been made in the synthesis of oligosaccharides through the development of new glycosyl donors 11 and advanced protecting group chemistry. 12 However, little work has been reported on the development of technology for the combinatorial synthesis of oligosaccharides. Kahne and coworkers used a protocol of splitting and mixing beads during the synthesis in combination with the use of chemical tagging at each combinatorial step. 13 By screening the library prepared in this combinatorial fashion against a flower lectin, they discovered new carbohydrate ligands with a higher affinity to the protein than the natural ligand. 13 On the other hand, a straightforward oligosaccharide library synthesis was reported by Kanie, et al., which involves an orthogonal glycosylation method on a polymeric support. 14 These methods use the solidphase technique which presents several limitations such as decreased glycosylation reaction © 2009 Elsevier Ltd. All rights reserved.Correspondence to: Eun Ju Kim. Publisher's Disclaimer: This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is p...

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A Method of Orthogonal Oligosaccharide Synthesis Leading to a Combinatorial Library Based on Stationary Solid‐Phase Reaction

Cited by 30 publications

References 106 publications

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

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

Addressing the glycan complexity by using mass spectrometry: In the pursuit of decoding glycologic

Use of ionically tagged glycosyl donors in the synthesis of oligosaccharide libraries

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