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Role of the orientation of -OH groups in the sensitivity and selectivity of the interactions of M<sup>2+</sup> with ribosyl- and galactosyl-imino-conjugates

hal.structure.identifierBioinorganic Laboratory, Department of Chemistry
dc.contributor.authorSINGHAL, Nitin K.
hal.structure.identifierBioinorganic Laboratory, Department of Chemistry
dc.contributor.authorMITRA, Atanu
hal.structure.identifierBioinorganic Laboratory, Department of Chemistry
dc.contributor.authorRAJSEKHAR, Gudneppanavar
hal.structure.identifierBioinorganic Laboratory, Department of Chemistry
dc.contributor.authorSHAIKH, Mobin M.
hal.structure.identifierBioinorganic Laboratory, Department of Chemistry
dc.contributor.authorKUMAR, Subodh
hal.structure.identifierInstitut de Chimie de la Matière Condensée de Bordeaux [ICMCB]
dc.contributor.authorGUIONNEAU, Philippe
hal.structure.identifierBioinorganic Laboratory, Department of Chemistry
dc.contributor.authorRAO, Chebrolu P.
dc.date.issued2009
dc.identifier.issn1477-9226
dc.description.abstractEnThree glyco-conjugates, viz., L<sub>1</sub>, L<sub>2</sub> and L<sub>3</sub>, which differ either in their carbohydrate moiety or in their aromatic moiety or both, were synthesized and characterized and were shown to have -anomeric form based on <sup>1</sup>H NMR and optical rotation studies. Metal ion interaction studies carried out in solution by emission and absorption spectral techniques exhibited selectivity towards Cu<sup>2+</sup> in HEPES buffer and a two fold higher sensitivity for L<sub>2</sub> as compared to L<sub>1</sub>. The composition of the complexed species has been established based on ESI MS. Dinuclear-Cu(II) complexes of all these conjugates have been synthesized and characterized based on analytical and spectral methods including FTIR, <sup>1</sup>H NMR, FAB MS, EPR, ORD, CD and magnetism, and the structures of <strong>1</strong> and <strong>3</strong> have been established based on single crystal XRD. The structures revealed subtle differences present in the orientation of the –OH groups and also their ion binding preferences both at the molecular level as well as at the lattice levels. In the dinuclear-Cu(II) complexes, while C3-O<sup>-</sup> of ribosyl acts as a bridging moiety in <strong>1</strong>, it is the C2-O<sup>-</sup> of galactosyl that bridges in <strong>3</strong> and the Cu<sub>2</sub>O<sub>2</sub> cores are stabilized by two intra-complex H-bond interactions formed using C4-OH in the case of <strong>1</strong> and C3-OH in the case of <strong>3</strong>. While the glyco-moiety is poised perpendicular to the average plane of the Cu<sub>2</sub>O<sub>2</sub> core in <strong>1</strong>, this is in plane in the case of <strong>3</strong>.
dc.language.isoen
dc.publisherRoyal Society of Chemistry
dc.title.enRole of the orientation of -OH groups in the sensitivity and selectivity of the interactions of M<sup>2+</sup> with ribosyl- and galactosyl-imino-conjugates
dc.typeArticle de revue
dc.identifier.doi10.1039/b903668g
dc.subject.halChimie/Matériaux
bordeaux.journalDalton Transactions
bordeaux.page8432-8442
bordeaux.issue39
bordeaux.peerReviewedoui
hal.identifierhal-00435828
hal.version1
hal.popularnon
hal.audienceInternationale
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-00435828v1
bordeaux.COinSctx_ver=Z39.88-2004&amp;rft_val_fmt=info:ofi/fmt:kev:mtx:journal&amp;rft.jtitle=Dalton%20Transactions&amp;rft.date=2009&amp;rft.issue=39&amp;rft.spage=8432-8442&amp;rft.epage=8432-8442&amp;rft.eissn=1477-9226&amp;rft.issn=1477-9226&amp;rft.au=SINGHAL,%20Nitin%20K.&amp;MITRA,%20Atanu&amp;RAJSEKHAR,%20Gudneppanavar&amp;SHAIKH,%20Mobin%20M.&amp;KUMAR,%20Subodh&amp;rft.genre=article


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