Description
L-Cyclohexylalanine is a kind of amino acid analog. It has some pharmacological effects. Study has shown that some of its derivatives exhibit potent bactericidal activity against drug-resistant gram-positive pathogens. Its derivatives can also act as dipeptidyl peptidase-IV inhibitor, which can be used for the treatment or prevention of diabetes.
References
http://nizetlab.ucsd.edu/Publications/CombinatorialLibrary.pdf
Duffy, Joseph L, et al. "Cyclohexylalanine derivatives as dipeptidyl peptidase-IV inhibitors for the treatment or prevention of diabetes." CN, CN 1960990 A. 2007.
Aarstad, K, T. L. Zimmer, and S. G. Laland. "The fidelity of gramicidin S synthetase." European Journal of Biochemistry 112.2(1980):335-338.
Chemical Properties
white to light yellow crystal powder
Uses
(S)-(+)-Cyclohexylalanine
Synthesis
Example 2: Preparation of L-cyclohexylalanine
Dissolve or suspend 20 g (121 mmol) of L-phenylalanine in a mixture of 200 ml of deionized water, 200 ml of isopropanol and 12.2 ml (146 mmol) of 37% hydrochloric acid. 2 g of Pt/Rh catalyst (4% Pt + 1% Rh loaded on activated carbon with ~50% water content, corresponding to ~5 wt% by mass of L-phenylalanine) was added. The reaction mixture was transferred to an 11-gallon hydrogenation autoclave. It was displaced three times with nitrogen and then flushed twice with hydrogen, followed by establishing a hydrogen pressure of 8-10 bar and heating the reaction system to 50-60°C. After about 6 to 8 hours of reaction, the hydrogen uptake was completed (theoretical H2 uptake of 8.1 L). The hydrogenator was depressurized and replaced with nitrogen again three times. The reaction mixture was filtered while hot through a nut filter and the catalyst was washed with 50 ml of deionized water. The filtrate was first concentrated to a smaller volume under reduced pressure (mainly to remove isopropanol), followed by adjusting the pH of the residue to 5-6 with 50% sodium hydroxide solution. the solution was cooled to 0-10 °C, the product was collected with a nut filter, washed with 50 ml of deionized water and dried in a vacuum oven at 50-70 °C. The reaction mixture was then purified with nitrogen. Yield: 19.5 g (94.2%).
1H-NMR (500 MHz, D2O/NaOD): δ (ppm) = 0.85-1.0, 1.1-1.52, and 1.63-1.75 (all multiple peaks totaling 13H, cyclohexyl-H, and cyclohexyl-CH2), 3.3 (triple peak, 1H, α-H).
References
[1] Tetrahedron, 1992, vol. 48, # 2, p. 307 - 318
[2] Journal of Organic Chemistry, 1988, vol. 53, # 4, p. 873 - 875
[3] Organic Process Research and Development, 2003, vol. 7, # 2, p. 164 - 167
[4] Patent: WO2005/14526, 2005, A1. Location in patent: Page/Page column 14
[5] Journal of Organometallic Chemistry, 2016, vol. 812, p. 81 - 86
