Templating and Catalyzing [2+2] Photocycloaddition in Solution Using a Dynamic G-Quadruplex. Academic Article

abstract

• We describe a templating/covalent capture strategy that enables photochemical formation of 8 cyclobutanes in one noncovalent assembly. This process was characterized by experiment and quantum mechanical/molecular mechanics (ONIOM) calculations. Thus, KI and 16 units of 5'-cinnamate guanosine form a G-quadruplex where C=C bonds in neighboring G4 -quartets are separated by 3.3, enabling [2+2] photocycloaddition in solution. This reaction is high-yielding (>90%), regio- and diastereoselective. Since all components are in dynamic equilibrium this photocycloaddition is catalytic in K+ .

authors

• Gutierrez Santacruz, Osvaldo

published proceedings

• Angew Chem Int Ed Engl

altmetric score

• 5.3

author list (cited authors)

• Sutyak, K. B., Lee, W., Zavalij, P. V., Gutierrez, O., & Davis, J. T.

citation count

• 13

complete list of authors

• Sutyak, Keith B||Lee, Wes||Zavalij, Peter V||Gutierrez, Osvaldo||Davis, Jeffery T

publication date

• January 2018

publisher

• Wiley  Publisher

published in

• Angewandte Chemie International Edition  Journal

keywords

• G-quadruplex
• Oniom (qm:mm)
• Photochemistry
• Self-assembly
• Supramolecular Catalysis
• Templated Synthesis

PubMed Central ID

• 30395701

Digital Object Identifier (DOI)

• 10.1002/anie.201811202

start page

• 17146

end page

• 17150

volume

• 57

issue

• 52

URL

• http://dx.doi.org/10.1002/anie.201811202