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Enzymatic separation of epimeric 4--hydroxymethylated furanosugars: Synthesis of bicyclic nucleosides.
Beilstein J Org Chem
October 2017
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi-110 007, India.
Conversion of D-glucose to 4-hydroxymethyl-1,2--isopropylidene-α-D-ribofuranose, which is a key precursor for the synthesis of different types of bicyclic/spiro nucleosides, led to the formation of an inseparable 1:1 mixture of the desired product and 4-hydroxymethyl-1,2--isopropylidene-α-D-xylofuranose. A convenient environment friendly Novozyme-435 catalyzed selective acetylation methodology has been developed for the separation of an epimeric mixture of ribo and xylotrihydroxyfuranosides in quantitative yields. The structure of both the monoacetylated epimers, i.
View Article and Find Full Text PDFSynthesis and biological evaluation of conformationally restricted adenine bicycloribonucleosides.
Org Biomol Chem
September 2015
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Gilead Sciences & IOCB Research Centre, 166 10 Prague 6, Czech Republic.
We prepared a novel series of conformationally restricted bicyclonucleosides and nucleotides. The synthetic approach employed a ring closing metathesis to provide access to both 6 and 7 membered saturated and unsaturated rings linking the 3' to 5' methylene groups of the sugar. The bicyclonucleosides were also transformed to the corresponding phosphoramidate prodrugs by an innovative one-pot protocol of boronate ester protection, coupling of the phosphoryl chloridate and deprotection of the boronate.
View Article and Find Full Text PDFSynthesis and biological evaluation of 2,6-dichloropurine bicyclonucleosides containing a triazolyl-carbohydrate moiety.
Carbohydr Res
December 2013
School of Pharmaceutical Sciences and New Drug Research & Development Center, Zhengzhou University, Zhengzhou 450001, PR China.
A series of bicyclic nucleosides containing a triazolyl-carbohydrate moiety were synthesized and their antitumor activity in vitro for human cancer cell lines was also tested. Compound 11 was synthesized efficiently with 3,6-anhydro sugar 7 as raw material, while compound 7 was prepared from 1,2;5,6-di-O-isopropylidene-α-d-glucose. Compounds 12a-e were synthesized by treating compound 11 with alkynes, catalyzed by copper(I).
View Article and Find Full Text PDFSynthesis of bicyclonucleosides having a C-C bridge.
Chem Rev
June 2010
Université de Nantes, CNRS, Laboratoire CEISAM-UMR-CNRS 6230, Faculté des Sciences et des Techniques, BP 92208, 44322 Nantes Cedex 3, France.
Greener biocatalytic approach to the synthesis of nucleosides and their precursors.
Nucleic Acids Symp Ser (Oxf)
November 2010
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi-110 007, India.
Novel, efficient and selective biocatalytic acylation / deacylation strategies have been used for the greener synthesis of precursors of different bicyclonucleosides. Biocatalytic methodology has also been developed for the separation of pyrano- and furanonucleosides, which is otherwise almost impossible to achieve by usual chemical approach.
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