Discipline: Chemistry and Chemical Sciences
Subcategory: Chemistry (not Biochemistry)
Sulihat Mudasiru - Texas A&M University - Commerce
Co-Author(s): Stephen Starnes, Texas A&M University-Commerce, TX
Biological molecules such as proteins exist as chirally pure single enantiomers which selectively recognize chiral substrates or selectively catalyze the biosynthesis of single enantiomer chiral products. This project aims to mimic biological molecules in the body. In this report, host complexes consisting of tetraphenylporphyrins (TTP) diamino-1,1-binapthalene were synthesized by attaching (S)-(-) 2, 2-diamino-1,1-binapthalene and (R)-(+)-2,2-diamino-1,1-binapthalene to TTP isocyanate in order to improve the selectivity of this host in its chiral guest binding properties, with the ultimate goal of studying affinities of host to the guests. Chiral guests studied were L-nicotine, R and S mandelate, and D-n-acetyl and L-n-acetyl phenylalanine. Proton NMR, Mass spectrometry, UV-Vis and CD spectroscopy were used to characterize the compounds and study their chiral host-guest binding properties. We proposed that R-guests will bind selectively with R-TTP host molecules while S-guest will bind preferentially to S-TTP molecules. L-Nicotine was found to show moderate selectivity with the S-TTP complex compared to other guests studied that showed little to no selectivity in the host-guest complex. Future work will focus on synthesizing new host-guest complexes and studying their chiral recognition properties.
References: Lehn, Jean-Marie. ‘Supramolecular Chemistry- Scope and Perspectives: Molecules Supermolecules- Molecular Devices.’ Journal of Inclusion Phenomena 6.4 (1988): 351-96.
Smith, Janice Gorzynski. 3rd ed. New York: McGraw-Hill, 2011.Wu, Xiaowen, and Stephen D. Starnes. ‘L -Nipecotic Acid-Porphyrin. Derivative: Chiral Host with Introverted Functionality for Chiral Recognition.’ Org. Lett. Organic Letters 14.14 (2012): 3652-655.
Wu, Xiaowen, and Stephen D. Starnes. ‘L -Nipecotic Acid-Porphyrin. Derivative: A Chiral Host with Introverted Functionality for Chiral Recognition.’ Org. Lett. Organic Letters 14.14 (2012): 3652-655.
Funder Acknowledgement(s): I would like to thank my mentor, Stephen Starnes for his help throughout this project. Funding was from the National Science Foundation -REU program. Materials for the project were obtained from Chemistry Department at Texas A & M University, Commerce.
Faculty Advisor: Stephen Starnes, firstname.lastname@example.org
Role: I completed all parts of this project on my own, my advisor assisted by answering any questions I had relating to my methods, in my results analysis and discussion.