Synthesis of a library of fucopyranosyl-galactopyranosides consisting of a complete set of anomeric configurations and linkage positions

Ohtsuka, Isao; Ako, Takuro; Kato, Rumiko; Daikoku, Shusaku; Koroghi, Satomi; Kanemitsu, Takuya; Kanie, Osamu

doi:10.1016/j.carres.2006.03.040

Cited by 30 publications

(24 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We synthesized all disaccharides used in the experiments [28,29]. Synthesis was performed on a small scale where stereoselectivity was not controlled to obtain all anomers in one sequence of reactions.…”

Section: Methodsmentioning

confidence: 99%

“…Thus, the mixtures of compounds obtained were finally isolated using reversephase HPLC to attain pure individual compounds. Synthetic details and assignment of the compounds were previously reported [29].…”

Section: Methodsmentioning

confidence: 99%

“…A series of naturally occurring oligosaccharides is not considered to contain sufficient information to extract any generalities regarding anomeric configurations and linkage positions. In this regard, a series of compounds (16 isomers) that we have synthesized, consisting of all possible isomeric structures with a Fuc-Gal sequence, is considered to be a good candidate as the information source [28,29]. We first analyzed these compounds by standard CID to see whether these closely related structures are distinguishable from one another.…”

Section: Cid Analysis Of All Compoundsmentioning

confidence: 99%

“…Here in this report, we describe the results of ERMS analysis of a small combinatorial library [28,29], consisting of a complete combination of compounds with a fucosyl galactose sequence and an important finding regarding anomeric structures.…”

mentioning

confidence: 99%

See 3 more Smart Citations

Discrimination of 16 structural isomers of fucosyl galactoside based on energy-resolved mass spectrometry

Daikoku

Ako

Kato

et al. 2007

J. Am. Soc. Mass Spectrom.

Self Cite

View full text Add to dashboard Cite

Glycans, a family of compounds often attached to proteins and ceramides, are diverse molecules involved in a wide range of biological functions. Their structural analysis is necessary and is often carried out at the microscale level. Methods based on mass spectrometry are therefore used, although they do not provide information regarding isomeric structures often found in glycan structures. If one finds "factors" characteristic of a certain isomer, this information can be used to elucidate an unknown oligosaccharide sequence. One potential technique is to use energy-resolved mass spectrometry (ERMS) that has been used to distinguish a pair of isomeric compounds. Thus, compounds in a combinatorial library might be effectively used for this purpose. We analyzed a set of 16 isomeric disaccharides, the structures of which consisted of all possible combinations of anomeric configurations and interglycosidic linkage positions. All of the compounds were distinguished based on ERMS where normal collision-induced dissociation could distinguish only seven compounds. Furthermore, it was shown that ␣-glycosidic linkages of fucose were more reactive than the ␣ ␤-isomers and the secondary glycosides were more reactive than the primary . The structural characteristics of oligosaccharides are quite different from those of other biopolymers such as nucleic acids and peptides. The diversity is generated from sequential combination in the latter two types of polymers, whereas anomers, ring size, linkage position, branching, and sequence are factors in the case of oligosaccharides [2]. Furthermore, the regulatory mechanisms for oligosaccharides still need to be clarified and synthesis, which is not template dependent, thus creates further molecular diversity called glycoforms. Despite the difficulties encountered in structural determination, there are reports on how glycosylation as a type of posttranslational modification (PTM) of protein affects glycoprotein secretion [3,4].

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Cid Analysis Of All Compoundsmentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Discrimination of 16 structural isomers of fucosyl galactoside based on energy-resolved mass spectrometry

Daikoku

Ako

Kato

et al. 2007

J. Am. Soc. Mass Spectrom.

Self Cite

View full text Add to dashboard Cite

show abstract

“…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

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Protecting Groups at the Secondary Positions of Carbohydrates

Vidal

Goekjian

2018

Protecting Groups

View full text Add to dashboard Cite

Synthesis of a library of fucopyranosyl-galactopyranosides consisting of a complete set of anomeric configurations and linkage positions

Cited by 30 publications

References 34 publications

Discrimination of 16 structural isomers of fucosyl galactoside based on energy-resolved mass spectrometry

Discrimination of 16 structural isomers of fucosyl galactoside based on energy-resolved mass spectrometry

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

Protecting Groups at the Secondary Positions of Carbohydrates

Contact Info

Product

Resources

About