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A self-assembled G-quadruplex formed by guanosine and borate as chiral scaffold was used to catalyze the asymmetric Friedel-Crafts reaction in water. Catalysis, depends on self-assembly of guanosine and borate into a fibrillar structure in the presence of Cu ion, can be modulated by assembly concentration, temperature and the amount of Cu ion. Detailed spectral experiments proved that the guanosine-based assembly in solution were responsible for the enantioselective catalysis, rather than small-molecule species. Some of similar G-quartet assemblies were unable to promote the asymmetric reaction, implying the unique properties of the current system including excellent lifetime stability and supramolecular chiral structures. This work provided the first example of self-assembled G-quadruplex achieving enantioselective catalysis and some perspective to better understand the design of nucleoside-based self-assemblies for enantioselective reaction. In view of guanosine as building block, these findings may be applied to discuss the prebiotic chiral catalysts preceded ribozymes.
This article was published in the following journal.
Name: The Journal of organic chemistry
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Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.
Esters formed between the aldehydic carbon of sugars and the terminal phosphate of guanosine diphosphate.
Guanosine 5'-(trihydrogen diphosphate), monoanhydride with phosphorothioic acid. A stable GTP analog which enjoys a variety of physiological actions such as stimulation of guanine nucleotide-binding proteins, phosphoinositide hydrolysis, cyclic AMP accumulation, and activation of specific proto-oncogenes.
Homer proteins belong to a family of adaptor and scaffold proteins which include Homer1, Homer2 and Homer3. Homer1 and Homer2 play a role in the regulation of calcium homeostasis, whereas Homer3 functions in stimulating changes in actin dynamics in neurons and T-cells. Homer proteins are best known as scaffold proteins at the post-synaptic density where they facilitate synaptic signaling. They function as a molecular switch in metabotropic glutamate receptor (MGluR) signaling, and are associated with human Fragile X syndrome.
Guanosine 5'-triphosphate 2'(3')-diphosphate. A guanine nucleotide containing five phosphate groups. Three phosphate groups are esterified to the sugar moiety in the 5' position and the other two in the 2' or 3' position. This nucleotide serves as a messenger to turn off the synthesis of ribosomal RNA when amino acids are not available for protein synthesis. Synonym: magic spot II.