92754-75-1Relevant academic research and scientific papers
Synthesis of new 3- and 4-substituted analogues of acyl homoserine lactone quorum sensing autoinducers
Olsen,Severinsen,Rasmussen,Hentzer,Givskov,Nielsen
, p. 325 - 328 (2007/10/03)
The quorum sensing mechanism in Gram-negative bacteria uses small intercellular signal molecules, N-acyl-homoserine lactones (AHLs), to control transcription of specific genes in relation to population density. In this communication, we describe the parallel synthesis of new AHL analogues, in which substituents have been introduced into the 3- and 4-positions of the lactone ring. These analogues have been screened for their ability to activate and inhibit a Vibrio fischeri LuxI/LuxR-derived quorum sensing reporter system.
A Novel Synthesis of the Monobactam Antibiotic Carumonam
Manchand, Percy S.,Luk, Kin-Chun,Belica, Peter S.,Choudhry, Satish C.,Wei, Chung Chen,Soukup, Milan
, p. 5507 - 5512 (2007/10/02)
A novel synthesis of the monobactam 4, a precursor of the antibiotic carumonam (3), has been achieved via the epoxide methyl (2R,3S)-4-acetoxy-2,3-epoxybutyrate (10).The latter was prepared from calcium L-threonate in three steps and 85percent overall yield.In a related study, ethyl (2R,3S)-4-hydroxy-2,3-epoxybutyrate (17) was prepared from L-(+)-tartaric acid in 45percent overall yield.Treatment of the sodium salt derived from 10 or 17 with ammonia led to a stereo- and regiospecific opening of the oxirane ring to give 20, after esterification, amide formation, and protection of the amino group.Conversion of 20 into 4 was accomplished by selective protection of the primary hydroxy group with chloroacetyl chloride, mesylation, sulfonation with 2-picoline-SO3, and ring closure with potassium bicarbonate.
