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. 2008 Sep;129(9):743-766.
doi: 10.1016/j.jfluchem.2008.06.007.

Fluorinated Nucleosides: Synthesis and Biological Implication

Peng Liu  1 , Ashoke Sharon, Chung K Chu
Affiliations

Fluorinated Nucleosides: Synthesis and Biological Implication

Peng Liu et al. J Fluor Chem. 2008 Sep.
No abstract available

PubMed Disclaimer

Figures

Figure 1
Figure 1
Common fluorinating agents
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
Scheme 5
Scheme 5
Scheme 6
Scheme 6
Scheme 7
Scheme 7
Scheme 8
Scheme 8
Figure 2
Figure 2
Scheme 9
Scheme 9
Scheme 10
Scheme 10
Scheme 11
Scheme 11
Scheme 12
Scheme 12
Scheme 13
Scheme 13
Scheme 14
Scheme 14
Scheme 15
Scheme 15
Scheme 16
Scheme 16
Scheme 17
Scheme 17
Scheme 18
Scheme 18
Scheme 19
Scheme 19
Scheme 20
Scheme 20
Scheme 21
Scheme 21
Figure 3
Figure 3
Scheme 22
Scheme 22
Scheme 23
Scheme 23
Scheme 24
Scheme 24
Scheme 25
Scheme 25
Scheme 26
Scheme 26
Scheme 27
Scheme 27
Figure 4a
Figure 4a
2′,3′-double bonds of (D4T, D4FC, 2′Fd4C, 2′F-4′Sd4C and Carbovir) are separated from the aromatic side chain of Tyr115 by 3.5 Å situated in parallel by the hydrophobic π—π interaction.
Figure 4b
Figure 4b
No steric hindrance is found between 4′-CH2 group (blue) of carbovir with Val184. However, 2′F-4′Sd4C with 4′-sulfur (red) experiences steric hindrance. L-Configured 3TC (yellow) also has steric hindrance with Val184.
Figure 5
Figure 5
a) L-3′F-4′Sd4C binds in the active site without steric hindrance with Met184. 3′-F showing H-bond with NH of Asp185. b) L-3′F-4′Sd4C in M184V HIV-1-RT, showing steric hindrance with V184 c) 3′-F group of D-3′F-4′Sd4C showing intramolecular interaction with β-phosphate causing unfavourable binding conformation
Scheme 28
Scheme 28
Scheme 29
Scheme 29
Scheme 30
Scheme 30
Scheme 31
Scheme 31
Scheme 32
Scheme 32
Scheme 33
Scheme 33
Scheme 34
Scheme 34
Scheme 35
Scheme 35
Scheme 36
Scheme 36
Scheme 37
Scheme 37
Figure 6
Figure 6
Some important biologically useful fluorinated nucleosides & their precursors
Figure 7
Figure 7
A viral polymerase model structure with DNA double strand (primer and template) and natural nucleoside,highlighting the position of catalytic polymerase site.
Scheme 38
Scheme 38
A plausible metabolic path of L-FMAU as a HBV polymerase inhibitor
See this image and copyright information in PMC

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