US-Africa Collaboration in Guided Inquiry Synthesis and Characterization of the “Frustrated” Amino Acid-Based Calixarene Molecules

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 18 (2013) pp 042-049
DOI 10.1007/s00897132462a

US-Africa Collaboration in Guided Inquiry Synthesis and Characterization of the “Frustrated” Amino Acid-Based Calixarene Molecules

Joseph K. Rugutt*,†, Kipgeno J. Rugutt‡, Michelle K. Johnson†, Julius Koske§, Denis Chirchir§, Gilbert Cheruiyot§, Joel Koech§, Erick Mibei§, Millie Chepkemoi Obel§, Joseph Choge§, Christine Chemutai Bii**, and Ronald Rop††

†Missouri State University-West Plains, Department of Chemistry, West Plains, MO 65775; ‡Illinois State University, Department of Educational Administration and Foundations, College of Education, DeGarmo 331, Campus Normal, IL 61790-5900; §School of Science & Technology, Department of Biological Sciences, Kabianga University College, Main Campus,20200, Kericho City, Kenya; **Research Scientist Medical Mycology, Center for Microbiology Research, Kenya Medical Research Institute, KNH 00202 Nairobi, Kenya; ††Laser and Optical Sciences Group, Department of Physics, Egerton University, Egerton 20115, Nakuru City, Kenya; JRugutt@MissouriState.edu
Received August 6, 2010. Accepted September 23, 2010.

Published: 22 Febuary 2013

Abstract. The Department of Chemistry at Missouri State University-West Plains (MSU-WP) is internationalizing the existing research activities by initiating a collaborative Kenya-U.S. Chiral Science (chiroscience) project. The overarching goalof the project is three-fold: 1) reinvigorate undergraduate research; 2) augment MSU-WP’s new Green Nanoscience Research and Mentoring Program; and 3) establish synergistic relationships between different research groups and academic institutions in Kenya and MSU-WP. To stimulate students’ interests in the collaborative chiroscience project, we have chosen projects that are not only aligned with NSF’s high priority areas but are also relevant to today’s society (e.g., cancer, tuberculosis, heart disease, HIV, and host-guest chemistry). For several years, our research groups have been working on two important supramolecular hosts, calixarenes and cyclodextrins (CDs). Calixarenes are macrocyclic structures with defined cavities, having host-guest complexation properties similar to CDs. One of the advantages that calixarenes have over naturally occurring host molecules, such as CDs, is that the size of the internal cavity of the macrocycle is more flexible, i.e., the number of constituent rings range from four to eight. This paper illustrates our ongoing efforts in the area of synthesis and complexation properties of calixarenes. Herein, we report the synthesis of new amino acid-based acylcalixarenes and characterization by means of ¹H- and ¹³C-NMR spectroscopy. The calix[4]arenes possess L-alanine, L-valine, L-leucine, and L-isoleucine moeties at the lower rim. 1D and 2D NMR showed that the new calixarenes adopt the standard “cone” conformations in solution.

Key Words: In the Classroom; organic chemistry; biochemistry

(*) Corresponding author. (E-mail: JRugutt@MissouriState.edu )

Article in PDF format (161 KB) HTML format