Title

Synthesis of nucleobase-calix[4]arene conjugates and evaluation of their self- assembly ability using NMR

Poster Number

24

Lead Author Major

Pre-Pharmacy

Format

Poster Presentation

Faculty Mentor Name

Liang Xue

Faculty Mentor Department

Chemistry

Abstract/Artist Statement

In the past few decades, a myriad of self-complementary compounds, which are able to undergo assembly, have been designed and synthesized. However, few of them have been made based on the DNA complementary base paring rule. This lack of progress could be due to the weak interactions between adenosine (A) and thymine (T) or uracil (U) and the difficulty of making suitable structures containing cytosine (C) and guanine (G). In this study, a series of analogues, nucleobases calix[4]arene conjugates, have been designed and synthesized by using “click” chemistry. The 1H-NMR solution studies, involving concentration, temperature and solvent dependence and NOE studies, have been carried out to determine the extent of assembly as well as what interactions occur between the bases. These studies demonstrate that small molecules containing nucleobases may be used to probe interactions in chemical and biological systems and to develop novel biological targeting agents. The molecules’ synthesis and the 1H-NMR studies of the assembly will be presented.

Location

DeRosa University Center, Ballroom

Start Date

21-4-2011 6:00 PM

End Date

21-4-2011 8:00 PM

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Apr 21st, 6:00 PM Apr 21st, 8:00 PM

Synthesis of nucleobase-calix[4]arene conjugates and evaluation of their self- assembly ability using NMR

DeRosa University Center, Ballroom

In the past few decades, a myriad of self-complementary compounds, which are able to undergo assembly, have been designed and synthesized. However, few of them have been made based on the DNA complementary base paring rule. This lack of progress could be due to the weak interactions between adenosine (A) and thymine (T) or uracil (U) and the difficulty of making suitable structures containing cytosine (C) and guanine (G). In this study, a series of analogues, nucleobases calix[4]arene conjugates, have been designed and synthesized by using “click” chemistry. The 1H-NMR solution studies, involving concentration, temperature and solvent dependence and NOE studies, have been carried out to determine the extent of assembly as well as what interactions occur between the bases. These studies demonstrate that small molecules containing nucleobases may be used to probe interactions in chemical and biological systems and to develop novel biological targeting agents. The molecules’ synthesis and the 1H-NMR studies of the assembly will be presented.