Design and synthesis of versatile ganglioside probes for carbohydrate microarrays

Imamura, Akira; Yoshikawa, Takeru; Komori, Tatsuya; Ando, Masayuki; Ando, Hiromune; Wakao, Masahiro; Suda, Yasuo; Ishida, Hideyuki; Kiso, Makoto

doi:10.1007/s10719-007-9102-8

Cited by 11 publications

(7 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Sugar chain-ligand conjugates 1 and 2 were used as the GM1 sugar moieties. The conjugates were prepared by reductive amination of a chemically synthesized GM1-Glc sugar component [ 22 ] and a commercially available GM1 sugar component (ELICITYL, Crolles, France), respectively, with a fluorescent linker molecule (f-mono, Fig 1 ) [ 21 ]. The preparation of SFNPs with these conjugates was performed using our previous method, with a slight modification ( Fig 1B ).…”

Section: Resultsmentioning

confidence: 99%

“…GM1-Glc-f-mono was synthesized according to the methods described in our previous report [ 21 ]. The GM1-Glc sugar chain [ 22 ] (1.0 mg, 0.86 μmol) and f-mono [ 21 ] (0.28 mg, 1.1 μmol) were dissolved in water (20 μL) and N , N -dimethylacetamide (30 μL), respectively. Then, the GM1-Glc solution and acetic acid (6 μL) were added to the f-mono solution.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Visual Detection of Human Antibodies Using Sugar Chain-Immobilized Fluorescent Nanoparticles: Application as a Point of Care Diagnostic Tool for Guillain-Barré Syndrome

et al. 2015

Self Cite

View full text Add to dashboard Cite

Sugar chain binding antibodies have gained substantial attention as biomarkers due to their crucial roles in various disorders. In this study, we developed simple and quick detection method of anti-sugar chain antibodies in sera using our previously developed sugar chain-immobilized fluorescent nanoparticles (SFNPs) for the point-of-care diagnostics. Sugar chain structure on SFNPs was modified with the sugar moieties of the GM1 ganglioside via our original linker molecule to detect anti-GM1 antibodies. The structures and densities of the sugar moieties immobilized on the nanoparticles were evaluated in detail using lectins and sera containing anti-GM1 antibodies from patients with Guillain-Barré syndrome, a neurological disorder, as an example of disease involving anti-sugar chain antibodies. When optimized SFNPs were added to sera from patients with Guillain-Barré syndrome, fluorescent aggregates were able to visually detect under UV light in three hours. The sensitivity of the detection method was equivalent to that of the current ELISA method used for the diagnosis of Guillain-Barré syndrome. These results suggest that our method using SFNPs is suitable for the point-of-care diagnostics of diseases involving anti-sugar chain antibodies.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Visual Detection of Human Antibodies Using Sugar Chain-Immobilized Fluorescent Nanoparticles: Application as a Point of Care Diagnostic Tool for Guillain-Barré Syndrome

et al. 2015

Self Cite

View full text Add to dashboard Cite

show abstract

“…The isolation of α-sialoside from the reaction mixture was easily accomplished by recrystallization [ 11 ]. The obtained disaccharide was readily converted into the corresponding trichloroacetimidate donor as Unit A [ 12 ]. Similarly, the other terminal Neu5Acα2-6Gal unit ( B ) was prepared efficiently according to the synthetic procedure for Unit A ( Scheme 1 ).…”

Section: Resultsmentioning

confidence: 99%

“…As a result of optimization, the desired α-glycoside 6 was obtained in 69% yield along with a 14% yield of the β-isomer. Purification of the α-glycoside 6 by silica gel column chromatography was troublesome compared with that of the regioisomer, Neu5Trocα2-3GalMP, which has benzyl groups on the O-2 and O-6 positions of its galactose residue, which can be isolated easily by recrystallization from an EtOAc/ n -hexane system [ 12 ]. The selective deprotection of the Troc group with Zn–Cu [ 17 ] (giving 7 ) and the subsequent concomitant acetylation of the liberated amine and the hydroxyl group at the C-4 position of the galactose residue afforded compound 8 in excellent yield.…”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of a Novel Ganglioside Ligand for Influenza A Viruses †

et al. 2012

Self Cite

View full text Add to dashboard Cite

A novel ganglioside bearing Neuα2-3Gal and Neuα2-6Gal structures as distal sequences was designed as a ligand for influenza A viruses. The efficient synthesis of the designed ganglioside was accomplished by employing the cassette coupling approach as a key reaction, which was executed between the non-reducing end of the oligosaccharide and the cyclic glucosylceramide moiety. Examination of its binding activity to influenza A viruses revealed that the new ligand is recognized by Neuα2-3 and 2-6 type viruses.

show abstract

“…Since the original description of TLC overlay methodology, it has evolved and diversified over the years, in parallel with ELISA techniques [30,31], to include a wide variety of GSL array designs based on non-covalent and covalent immobilization of GSLs and GSL analogues [10,16,[32][33][34][35][36]. In one interesting case, the ganglioside G M1 was incorporated into an immobilized fluid supported lipid bilayer approximating display in a cell membrane [37].…”

Section: Introductionmentioning

confidence: 99%

Design of a covalently bonded glycosphingolipid microarray

et al. 2011

View full text Add to dashboard Cite

Glycosphingolipids (GSLs) are well known ubiquitous constituents of all eukaryotic cell membranes, yet their normal biological functions are not fully understood. As with other glycoconjugates and saccharides, solid phase display on microarrays potentially provides an effective platform for in vitro study of their functional interactions. However, with few exceptions, the most widely used microarray platforms display only the glycan moiety of GSLs, which not only ignores potential modulating effects of the lipid aglycone, but inherently limits the scope of application, excluding, for example, the major classes of plant and fungal GSLs. In this work, a prototype "universal" GSL-based covalent microarray has been designed, and preliminary evaluation of its potential utility in assaying protein-GSL binding interactions investigated. An essential step in development involved the enzymatic release of the fatty acyl moiety of the ceramide aglycone of selected mammalian GSLs with sphingolipid N-deacylase (SCDase). Derivatization of the free amino group of a typical lyso-GSL, lyso-G(M1), with a prototype linker assembled from succinimidyl-[(N-maleimidopropionamido)-diethyleneglycol] ester and 2-mercaptoethylamine, was also tested. Underivatized or linker-derivatized lyso-GSL were then immobilized on N-hydroxysuccinimide- or epoxide-activated glass microarray slides and probed with carbohydrate binding proteins of known or partially known specificities (i.e., cholera toxin B-chain; peanut agglutinin, a monoclonal antibody to sulfatide, Sulph 1; and a polyclonal antiserum reactive to asialo-G(M2)). Preliminary evaluation of the method indicated successful immobilization of the GSLs, and selective binding of test probes. The potential utility of this methodology for designing covalent microarrays that incorporate GSLs for serodiagnosis is discussed.

show abstract

Design and synthesis of versatile ganglioside probes for carbohydrate microarrays

Abstract: A series of ganglioside GM1-, GM2-, and GM3-type probes, in which the ceramide portion is replaced with a glucose residue, were systematically synthesized based on a convergent synthetic method.

Cited by 11 publications

References 24 publications

Visual Detection of Human Antibodies Using Sugar Chain-Immobilized Fluorescent Nanoparticles: Application as a Point of Care Diagnostic Tool for Guillain-Barré Syndrome

Visual Detection of Human Antibodies Using Sugar Chain-Immobilized Fluorescent Nanoparticles: Application as a Point of Care Diagnostic Tool for Guillain-Barré Syndrome

Design and Synthesis of a Novel Ganglioside Ligand for Influenza A Viruses †

Design of a covalently bonded glycosphingolipid microarray

Contact Info

Product

Resources

About