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Article: Synthesis and Biological Evaluation of α-D-Mannopyranoside-Containing Dendrimers
Title | Synthesis and Biological Evaluation of α-D-Mannopyranoside-Containing Dendrimers |
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Authors | |
Issue Date | 1998 |
Citation | Journal of Organic Chemistry, 1998, v. 63, n. 10, p. 3429-3437 How to Cite? |
Abstract | The extension of dendritic synthetic principles to the preparation of new kinds of dendrimer-based glycoconjugate systems has been investigated. A convergent growth approach to the synthesis of α-D-mannopyranoside-containing dendrimers of various generations has been used successfully to obtain high molecular weight and monodisperse dendrimers in which 3-36 identical copies of the mannopyranoside residues are located at their peripheries. A repetitive synthetic sequence for forming amide bonds is employed in the preparation of various dendritic wedges and their attachment to a 1,3,5-trisubstituted benzenoid core in the last step. The protecting groups on the saccharide residues are then finally removed to obtain free saccharide-containing dendrimers. The efficacy of these dendrimers in inhibiting the binding of concanavalin A lectin to a purified yeast mannan fraction (as measured by an enzyme-linked lectin assay) is shown to be about four times more pronounced on a molar basis for the dendrimers possessing nine, 18, and 36 mannose residues, when compared to a dendritic wedge possessing three mannose residues and methyl α-D-mannopyranoside as control inhibitors. |
Persistent Identifier | http://hdl.handle.net/10722/332303 |
ISSN | 2023 Impact Factor: 3.3 2023 SCImago Journal Rankings: 0.724 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Ashton, Peter R. | - |
dc.contributor.author | Hounsell, Elizabeth F. | - |
dc.contributor.author | Jayaraman, Narayanaswamy | - |
dc.contributor.author | Nilsen, Torill M. | - |
dc.contributor.author | Spencer, Neil | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.contributor.author | Young, Mia | - |
dc.date.accessioned | 2023-10-06T05:10:25Z | - |
dc.date.available | 2023-10-06T05:10:25Z | - |
dc.date.issued | 1998 | - |
dc.identifier.citation | Journal of Organic Chemistry, 1998, v. 63, n. 10, p. 3429-3437 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/10722/332303 | - |
dc.description.abstract | The extension of dendritic synthetic principles to the preparation of new kinds of dendrimer-based glycoconjugate systems has been investigated. A convergent growth approach to the synthesis of α-D-mannopyranoside-containing dendrimers of various generations has been used successfully to obtain high molecular weight and monodisperse dendrimers in which 3-36 identical copies of the mannopyranoside residues are located at their peripheries. A repetitive synthetic sequence for forming amide bonds is employed in the preparation of various dendritic wedges and their attachment to a 1,3,5-trisubstituted benzenoid core in the last step. The protecting groups on the saccharide residues are then finally removed to obtain free saccharide-containing dendrimers. The efficacy of these dendrimers in inhibiting the binding of concanavalin A lectin to a purified yeast mannan fraction (as measured by an enzyme-linked lectin assay) is shown to be about four times more pronounced on a molar basis for the dendrimers possessing nine, 18, and 36 mannose residues, when compared to a dendritic wedge possessing three mannose residues and methyl α-D-mannopyranoside as control inhibitors. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of Organic Chemistry | - |
dc.title | Synthesis and Biological Evaluation of α-D-Mannopyranoside-Containing Dendrimers | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/jo9804184 | - |
dc.identifier.scopus | eid_2-s2.0-0001574886 | - |
dc.identifier.volume | 63 | - |
dc.identifier.issue | 10 | - |
dc.identifier.spage | 3429 | - |
dc.identifier.epage | 3437 | - |
dc.identifier.isi | WOS:000073769600044 | - |