1379456-24-2

Upstream product

• 2885-10-1 L-Phenylalanine buthylester 
• 6330-15-0 L-phenylalanine n-butyl ester hydrochloride 
• 63-91-2 L-phenylalanine 
• 616-47-7 1-methyl-1H-imidazole 
• 1379456-13-9 butyl (2-bromoacetyl)-L-phenylalaninate 

Relevant academic research and scientific papers

Synthesis, self-assembly, bacterial and fungal toxicity, and preliminary biodegradation studies of a series of l-phenylalanine-derived surface-active ionic liquids

We report for the first time a comprehensive study on the synthesis (supported by green chemistry metrics), aggregation properties, bacterial/fungal toxicities and preliminary data on biodegradation of a series of 24 l-phenylalanine derived surface-active ionic liquids (SAILs). The various cationic headgroups included pyridinium, imidazolium, and cholinium groups and enabled a comprehensive analysis of the effect of the alkyl ester chain (from C2 to C16) on the synthesis, toxicity, biodegradability, and surfactant properties of the novel SAILs. The evaluation of the SAILs revealed that a wide variety of properties were strictly dependent on the side chain length, including their bacterial and fungal toxicities (from low toxicity to high toxicity), and aggregation properties. Addition of the l-phenylalanine moiety which connects the lipophilic side chain to the cationic head group results in the phenyl group essentially contributing to the self-assembling properties. The interplay of dispersion interactions of the phenyl ring and the side chain hydrophobicity allows us to rank the novel SAILs (thus identifying the remarkable ones) as compared to other surfactants. The CMC values for the SAILs reported in this study are significantly (up to 10 times) lower than those reported for conventional surfactants with the same length of the side chain. Adsorption and micellization are among the factors affecting the toxicity of the studied SAILs. Preliminary biodegradation studies have shown that no clear trend was observed when comparing the closed bottle test results of the SAIL C2 and C10 derivatives. Medium chain length (C6 to C8) pyridinium SAILs have been recommended as the most prospective green alternatives for conventional cationic surfactants. These findings can contribute to designing new efficient amphiphiles with optimized antimicrobial activities and to employ them as potential environmentally benign mineralisable surfactants.

Antimicrobial toxicity studies of ionic liquids leading to a 'hit' MRSA selective antibacterial imidazolium salt

Imidazolium salts can be classed as surfactants, detergents, ionic liquids, reagents, catalysts or solvents. A study of the toxicity and ecotoxicity of these salts yields valuable information for their use as pharmaceuticals as well as impact on the environment. Our approach to screen a series of chiral imidazolium salts for toxicity to bacteria and fungi, including clinical pathogen strains, has led to the identification of a 'hit' MRSA selective antimicrobial compound. Preliminary structure-activity-relationship (SAR) information (required position of l-phenylalanine and l-valine group) is also elucidated within this first generation of compounds. Conversely, most of the imidazolium salts were nontoxic (IC95 > 2 mM) to the 12 fungi strains and 8 bacteria strains screened, and we propose that they are suitable candidates for 'green chemistry' applications. Ecotoxicity studies (Biodegradation ISO 14593 'CO2 Headspace Test') of two bromide ionic liquids containing l-phenylalanine residues indicate that these ionic liquids passed the test (>60% in 28 days) and classed as readily biodegradable.