56217-77-7

Upstream product

• 150-30-1 Phenylalanine 
• 142-61-0 Hexanoyl chloride 
• 142-62-1 hexanoic acid 

Relevant academic research and scientific papers

Optimization of amino acid thioesters as inhibitors of metallo-β-lactamase L1

The emergence of antibiotic resistance caused by metallo-β-lactamases (MβLs) is a global public health problem. Recently, we found amino acid thioesters to be a highly promising scaffold for inhibitors of the MβL L1. In order to optimize this series of inhibitors, nine new amino acid thioesters were developed by modifying the substituents on the N-terminus of the thioesters and the groups representing the amino acid side chain. Biological activity assays indicate that all of them are very potent inhibitors of L1 with an IC50value range of 20–600?nM, lower than those of most of the previously reported inhibitors of this scaffold. Analysis of structure–activity relationship reveals that big hydrophobic substituents on the N-terminus and a methionine amino acid side chain improves inhibitory activity of the thioesters. All these inhibitors are able to restore antibacterial activity of a β-lactam antibiotic against Escherichia coli BL21(DE3) cells producing L1 to that against E. coli cells lacking a β-lactamase. Docking studies reveal that a large N-terminal hydrophobic group results in a slightly different binding mode than smaller hydrophobic groups at the same position.

Composition containing a penem or carbapenem antibiotic and the use of the same

Administration of an N-acylated amino acid in association with a penem or carbapenem antibiotic relieves or eliminates the renal problems associated with administration of the antibiotic alone. The amino acid derivative and antibiotic may be formulated together as a composition or administered separately, either simultaneously or sequentially.

Enhancement of the rectal absorption of sodium ampicillin by N-acylamino acids in rats

The promoting efficacies of N-acyl derivatives of amino acids on the rectal absorption of sodium ampicillin were investigated using the rat rectal loop technique. N-Acyl derivatives with longer carbon chains in the acyl moiety showed a greater promoting potency. The promoting potencies of N-acyl derivatives of phenylglycine and phenyl-alanine were greater than those of glycine and alanine derivatives when compared at the same length of carbon chain in their acyl moieties. The promoting action of N-acylamino acids was not influenced by the presence of N-ethylmaleimide or ouabain. The promoting potencies of N-acylamino acids were depressed in the presence of calcium chloride in the rectal loop. The contribution of the calcium ion sequestration capacity of N-acylamino acids to their promoting efficacies is discussed.

Resolution of N-acyl-DL (+)-phenylalanines

The treatment of N-acyl-DL(+)-phenylalanines with D(-)-2-(2,5-dimethylbenzylamino)-1-butanol results in the formation of the D(-)-2-(2,5-dimethylbenzylamino)-1-butanol salt which is obtained as a crystallizate of the N-acyl-L(+)-phenylalanine and from which the desired N-acyl-L(+)-phenylalanine, an intermediate useful for the preparation of artificial sweetening agents, can be recovered.