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1 article(s) from Rejman, Dominik

Pyrrolidine nucleotide analogs with a tunable conformation

Lenka Poštová Slavětínská,
Dominik Rejman and
Radek Pohl

Beilstein J. Org. Chem. 2014, 10, 1967–1980, doi:10.3762/bjoc.10.205

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Graphical Abstract

Figure 1: Examples of biologically active acyclic and cyclic nucleotide analogs.

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Figure 2: The pyrrolidine nucleotide analogs investigated in this study.

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Scheme 1: The synthesis of pyrrolidine nucleotides 7–14.

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Figure 3: The numbering of the pyrrolidine ring, the nucleobase and the endocyclic phase angles for the purpo...

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Figure 4: The aliphatic part (pyrrolidine protons) of the ¹H NMR spectra of 9 measured in D₂O at different pD...

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Figure 5: Changes of selected ¹H and ¹³C chemical shifts of 9 upon pD change.

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Figure 6: The deuteration equilibria of phosphonomethyl derivatives 7–10.

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Figure 7: The aliphatic part (pyrrolidine protons) of the ¹H NMR spectra of 13 measured in D₂O at different p...

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Figure 8: Amide rotamers of phosphonoformyl derivatives 11–14.

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Figure 9: The ³¹P NMR spectra (202.3 MHz) of 14 measured (the black curve) and simulated (the red curve) at v...

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Figure 10: A part of the H,C-HSQC spectrum of derivative 13, showing the assignment of rotamers A and B.

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Figure 11: The pseudorotation pathway of the pyrrolidine ring in the compounds studied. The sign B stands for ...

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Figure 12: An example of the stereospecific assignment of pyrrolidine-ring protons of 14 in the H,H-ROESY spec...

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Figure 13: The energy profile of the five-membered pyrrolidine ring pseudorotation for adenine derivatives 9 a...

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Figure 14: The most stable conformations of adenine derivatives 9 and 13A calculated by the B3LYP/6-31++G* met...

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Published 22 Aug 2014

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