A New Ligation Strategy for Peptide and Protein Glycosylation: Photoinduced Thiol–Ene Coupling

Dondoni, Alessandro; Massi, Alessandro; Nanni, Paolo; Roda, Aldo

doi:10.1002/chem.200901746

Cited by 133 publications

(106 citation statements)

References 64 publications

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“…Briefly, the antigens were synthesized with an alkene at the reducing end that was converted to the corresponding amine salt using a photochemically induced thiol-ene reaction with cysteamine. The amine was then coupled with di-p-nitrophenyl adipate to generate an activated ester derivative (23). These activated derivatives were reacted (22) with bovine serum albumin to give the neoglycoconjugates used the analyses.…”

Section: Methodsmentioning

confidence: 99%

Tulane Virus Recognizes the A Type 3 and B Histo-Blood Group Antigens

Zhang

Huang

Zou

et al. 2015

J Virol

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Tulane virus (TV), the prototype of the Recovirus genus in the calicivirus family, was isolated from the stools of rhesus monkeys and can be cultivated in vitro in monkey kidney cells. TV is genetically closely related to the genus Norovirus and recognizes the histo-blood group antigens (HBGAs), similarly to human noroviruses (NoVs), making it a valuable surrogate for human NoVs. However, the precise structures of HBGAs recognized by TV remain elusive. In this study, we performed binding and blocking experiments on TV with extended HBGA types and showed that, while TV binds all four types (types 1 to 4) of the B antigens, it recognizes only the A type 3 antigen among four types of A antigens tested. The requirements for HBGAs in TV replication were demonstrated by blocking of TV replication in cell culture using the A type 3/4 and B saliva samples. Similar results were also observed in oligosaccharide-based blocking assays. Importantly, the previously reported, unexplained increase in TV replication by oligosaccharide in cell-based blocking assays has been clarified, which will facilitate the application of TV as a surrogate for human NoVs. IMPORTANCEOur understanding of the role of HBGAs in NoV infection has been significantly advanced in the past decade, but direct evidence for HBGAs as receptors for human NoVs remains lacking due to a lack of a cell culture method. TV recognizes HBGAs and can replicate in vitro, providing a valuable surrogate for human NoVs. However, TV binds to some but not all saliva samples from A-positive individuals, and an unexplained observation of synthetic oligosaccharide blocking of TV binding has been reported. These issues have been resolved in this study.

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Section: Methodsmentioning

confidence: 99%

Tulane Virus Recognizes the A Type 3 and B Histo-Blood Group Antigens

Zhang

Huang

Zou

et al. 2015

J Virol

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“…Wittrock et al 182 first reported the use of the classical radical thiol-ene (thiyl-ene) reaction between thiols and olefins as a method for modifying thiol-containing proteins under ultraviolet irradiation. This has subsequently been exploited at both genetically encoded alkenes 169,183 and native cysteine residues 184 to generate glycoprotein mimics 169,184 , and for surface immobilisation of proteins 172 . A related reaction, the thiol-yne reaction with alkynes, has also been reported 100,185 .…”

Section: Modifications At Uaasmentioning

confidence: 99%

Selective chemical protein modification

2014

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“…The octenyl linker of 13 and 14 was further functionalized by first introducing a cysteamine residue via a UV-promoted thiol-ene reaction 33 to give the corresponding amines 15 and 16 as their hydrochloride salts in 90-97% yield (Scheme 2). Further elaboration of the linker using di-p-nitrophenyl adipate 34 in dimethylacetamide gave the highly reactive p-nitrophenol (PNP) esters 1 and 2.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of trisaccharides incorporating the α-Gal antigen functionalized for neoglycoconjugate preparation

Plaza-Alexander¹,

Lowary

2012

Arkivoc

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Dedicated to Professor Richard R. Schmidt on the occasion of his 78th anniversary AbstractThe synthesis of trisaccharides 1 and 2, which contain the α-D-galactopyranosyl-(1→3)-β-Dgalactopyranosyl (α-Gal) motif, is described. A key step in the synthesis of the trisaccharides was the glycosylation of a monosaccharide acceptor with a disaccharide trichloroacetimidate donor. Subsequent modification of the products of this [2+1] glycosylation afforded 1 and 2, which contain an activated ester moiety suitable for reaction with, for example, proteins or amine-coated surfaces.

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A New Ligation Strategy for Peptide and Protein Glycosylation: Photoinduced Thiol–Ene Coupling

Cited by 133 publications

References 64 publications

Tulane Virus Recognizes the A Type 3 and B Histo-Blood Group Antigens

Tulane Virus Recognizes the A Type 3 and B Histo-Blood Group Antigens

Selective chemical protein modification

Synthesis of trisaccharides incorporating the α-Gal antigen functionalized for neoglycoconjugate preparation

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