Ring-Closing Metathesis and Glycosylation Reactions: Synthesis and Biophysical Studies of Polyether-Linked Carbohydrate-Based Macrocyclic Nucleosides
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
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| Title |
Ring-Closing Metathesis and Glycosylation Reactions: Synthesis and Biophysical Studies of Polyether-Linked Carbohydrate-Based Macrocyclic Nucleosides
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| Creator |
Das, Soumendra Nath
Rana, Richa Chatterjee, Sabyasachi Kumar, Gopinatha Suresh Mandal, Sukhendu B |
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| Subject |
Chemistry
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| Description |
Bis-, tris-, and tetrakisuracil-substituted 12-, 13-,
17-, and 21-membered macrocyclic nucleoside analogues with
polyether linkages, including C2-symmetric molecules, have
been synthesized through coupling of two appropriately
allylated sugar derivatives, derived from D-glucose, followed
by a sequential ring-closing metathesis reaction using Grubbs
catalysts, double-bond reduction, and nucleoside base insertion
under Vorbrüggen reaction conditions. Spectroscopic studies
on the interaction of these nucleoside analogues with small
molecules, such as the alkaloids berberine and palmatine and
the DNA intercalator ethidium bromide, revealed a change in
the absorbance and fluorescence of the small molecules suggesting the potential use of these nucleoside molecules as a carrier of
small molecules in biological systems. Circular dichroism studies indicated that the complexes of the nucleosides with small
molecules undergo aggregation/self-organization. This has been further evidenced by a SEM experiment showing the binding of
berberine with one of the nucleoside derivatives, which confirms the occurrence of secondary structure reorganization.
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| Publisher |
American Chemical Society
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| Date |
2014
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://www.eprints.iicb.res.in/2156/1/JOURNAL_OF_ORGANIC_CHEMISTRY__Volume_79___Issue_21___Pages_9958%2D9969_;2014.pdf
Das, Soumendra Nath and Rana, Richa and Chatterjee, Sabyasachi and Kumar, Gopinatha Suresh and Mandal, Sukhendu B (2014) Ring-Closing Metathesis and Glycosylation Reactions: Synthesis and Biophysical Studies of Polyether-Linked Carbohydrate-Based Macrocyclic Nucleosides. The Journal of Organic Chemistry, 79 (21). pp. 9958-9969. |
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| Relation |
http://dx.doi.org/10.1021/jo501857k
http://www.eprints.iicb.res.in/2156/ |
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