Abstract
A range of surfactant analogues were synthesized from L-Tyrosine and L-Phenylalanine and tested for their catalytic and biological activity. Analogues (6), (7), (8), (9) were synthesized using the L-Tyrosine backbone whilst (10), (11), (12) were synthesized from L-Phenylalanine. Preliminary catalytic studies using both the analogues of L-Tyrosine and L-Phenylalanine were carried out on three main reactions; Baylis-Hillman, Michael addition and dipolar additions. For the Baylis-Hillman, the reaction between benzaldehyde and methyl acrylate was investigated where yields as high as 15% were generated when using (9) as catalyst. A phase-transfer solvent system was found to be the best medium to carry out these reactions. For the Michael addition reactions between dialkyl malonates and cyclic pentenones, the best yield was found to be at 70%, using L-Phenylalanine as catalyst. Selectivity enhancement was observed when adding an extended chain onto cyclopentenone where values of up to 69% e.e to the S-isomer were obtained using (12). Interestingly for the reaction between cyclopentenone and diethylmalonate higher and reversed selectivities (as high as 76% e.e, R-isomer) were observed using the Tyrosine analogues (6) and (8). The phenylalanine analogues (10), (11) and (12) were found to enhance the dipolar addition reaction between sarcosine and N-ethyl maleimide generating yields as high as 85% when using catalytic amounts of (12). Finally biological analysis showed that L-phenylalanine and N-propanoyl L-phenylalanine gave moderate activity for a range of gram (+) and gram (−)-bacteria.
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Acknowledgements
We are grateful to the following technical staff at University of Mauritius; Mr B. Jokhun and Miss S. L’Omlette, for the running of NMR, Mr V. Ramsahye for assistance during the polarimetry studies and Mrs M. Bissoondoyal for assistance during the Biological studies.
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Caumul, P., Joondan, N., Tuhaloo, A., Jhowry, T. (2012). Preliminary Catalytic Studies Using Tyrosine and Phenylalanine Analogues on Selected Baylis-Hillman and Michael Reactions. In: Gupta Bhowon, M., Jhaumeer-Laulloo, S., Li Kam Wah, H., Ramasami, P. (eds) Chemistry for Sustainable Development. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-8650-1_6
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