Related Experiment Video
Updated: Jun 8, 2026

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
Published on: April 3, 2014
A regio- and stereo-controlled approach to triazoloquinoxalinyl C-nucleosides
Adel Amer1, Mohammed Salah Ayoup, Sherine Nabil Khattab
1Department of Chemistry, Faculty of Science, PO Box 426 Ibrahimia, Alexandria University, Egypt. aamer@sci.alex.edu.eg
Abstract:
The synthesis of a new series of acyclic triazoloquinoxalinyl C-nucleosides and their transformation to their cyclic analogs are described following protection, activation, and deprotection with subsequent intramolecular nucleophilic substitution protocol. The antibacterial potency of the new compounds was determined using an inhibition zone diameter test. The results show that 3a and 2b exhibit good activity against Escherichiacoli and Candidaalbicans. On the other hand, the cyclic mesylated C-nucleoside 13 showed activity against the Gram-positive bacteria (Staphylococcusaureus) and antifungal activity against C. albicans.
Related Concept Videos
Antiviral Nucleoside Inhibitors
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Stereoisomerism of Cyclic Compounds
Inhibitors of Viral Protein Synthesis
Stereoisomers
SN1 Reaction: Stereochemistry
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...

