C2′-F Stereoconfiguration As a Puckering Switch for Base Stacking at the Dinucleotide Level

Autor: Dominique Guillaume, Jyoti Chattopadhyaya, Clément Denhez, Marcos Joel Vianelli Prado, Oleksandr Plashkevych, Céline Moriou, Adilson David da Silva, Pascale Clivio

Publikováno v: Journal of Organic Chemistry
Journal of Organic Chemistry, American Chemical Society, 2018, 83 (4), pp.2473-2478. ⟨10.1021/acs.joc.7b03186⟩

International audience; Fluorine configuration at C2′ of the bis(2′-fluorothymidine) dinucleotide is demonstrated to drive intramolecular base stacking. 2′-β F-Configuration drastically reduces stacking compared to the 2′-α series. Hence, b

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::2e937bfceca4384897edeed52214d52f
https://hal.archives-ouvertes.fr/hal-02380411

How RNase HI (Escherichia coli) promoted site-selective hydrolysis works on RNA in duplex with carba-LNA and LNA substituted antisense strands in an antisense strategy context?

Autor: Jyoti Chattopadhyaya, Oleksandr Plashkevych, Qing Li

Publikováno v: Molecular bioSystems. 13(5)

A detailed kinetic study of 36 single modified AON-RNA heteroduplexes shows that substitution of a single native nucleotide in the antisense strand (AON) by locked nucleic acid (LNA) or by diastereomerically pure carba-LNA results in site-dependent m

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::d0be7567d1e3c86c947ebe600675902f
https://pubmed.ncbi.nlm.nih.gov/28352859

Double Sugar and Phosphate Backbone-Constrained Nucleotides: Synthesis, Structure, Stability, and Their Incorporation into Oligodeoxynucleotides

Autor: Jyoti Chattopadhyaya, Oleksandr Plashkevych, Chuanzheng Zhou

Publikováno v: The Journal of Organic Chemistry. 74:3248-3265

Two diastereomerically pure carba-LNA dioxaphosphorinane nucleotides [(S(p))- or (R(p))-D(2)-CNA], simultaneously conformationally locked at the sugar and the phosphate backbone, have been designed and synthesized. Structural studies by NMR as well a

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::6fad257ba0d25517343d78b777174615
https://doi.org/10.1021/jo900391n

The chemical nature of the 2′-substituent in the pentose-sugar dictates the pseudoaromatic character of the nucleobase (pKa) in DNA/RNA

Autor: Dmytro Honcharenko, Subhrangsu Chatterjee, Jyoti Chattopadhyaya, Oleksandr Plashkevych, Mohitosh Maiti, Wimal Pathmasiri, Oommen P. Varghese

Publikováno v: Org. Biomol. Chem.. 4:1675-1686

We here show that the pKa (error limit: 0.01 to 0.03 pKa unit) of a nucleobase in a nucleotide can be modulated by the chemical nature of the 2'-substituent at the sugar moiety. This has been evidenced by the measurement of nucleobase pKa in 47 diffe

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7c267e6f75434a57837938332b5adda2
https://doi.org/10.1039/b601460g

Synthesis, Physicochemical and Biochemical Studies of 1‘,2‘-Oxetane Constrained Adenosine and Guanosine Modified Oligonucleotides, and Their Comparison with Those of the Corresponding Cytidine and Thymidine Analogues

Autor: Jyoti Chattopadhyaya, Pradeep Cheruku, Oleksandr Plashkevych, Parag Acharya, Pushpangadan Indira Pradeepkumar, Suresh Gohil

Publikováno v: Journal of the American Chemical Society. 126:11484-11499

We have earlier reported the synthesis and antisense properties of the conformationally constrained oxetane-C and -T containing oligonucleotides, which have shown effective down-regulation of the proto-oncogene c-myb mRNA in the K562 human leukemia c

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c91f17bc2ac16e0031ca546c49cf057a
https://doi.org/10.1021/ja048417i