Development of small-molecule inhibitors of fatty acyl-AMP and fatty acyl-CoA ligases in Mycobacterium tuberculosis was written by Baran, Marzena;Grimes, Kimberly D.;Sibbald, Paul A.;Fu, Peng;Boshoff, Helena I. M.;Wilson, Daniel J.;Aldrich, Courtney C.. And the article was included in European Journal of Medicinal Chemistry in 2020.Application In Synthesis of 12-Methoxy-12-oxododecanoic acid This article mentions the following:
Lipid metabolism in Mycobacterium tuberculosis (Mtb) relies on 34 fatty acid adenylating enzymes (FadDs) that can be grouped into two classes: fatty acyl-CoA ligases (FACLs) involved in lipid and cholesterol catabolism and long chain fatty acyl-AMP ligases (FAALs) involved in biosynthesis of the numerous essential and virulence-conferring lipids found in Mtb. The precise biochem. roles of many FACLs remain poorly characterized while the functionally non-redundant FAALs are much better understood. Here we describe the systematic investigation of 5′-O-[N-(alkanoyl)sulfamoyl]adenosine (alkanoyl adenosine monosulfamate, alkanoyl-AMS) analogs as potential multitarget FadD inhibitors for their antitubercular activity and biochem. selectivity towards representative FAAL and FACL enzymes. We identified several potent compounds including 12-azidododecanoyl-AMS, 11-phenoxyundecanoyl-AMS, and nonyloxyacetyl-AMS with min. inhibitory concentrations (MICs) against M. tuberculosis ranging from 0.098 to 3.13μM. Compound I was notable for its impressive biochem. selectivity against FAAL28 (apparent Ki = 0.7μM) vs. FACL19 (Ki > 100μM), and uniform activity against a panel of multidrug and extensively drug-resistant TB strains with MICs ranging from 3.13 to 12.5μM in minimal (GAST) and rich (7H9) media. The SAR anal. provided valuable insights for further optimization of I and also identified limitations to overcome. In the experiment, the researchers used many compounds, for example, 12-Methoxy-12-oxododecanoic acid (cas: 3903-40-0Application In Synthesis of 12-Methoxy-12-oxododecanoic acid).
12-Methoxy-12-oxododecanoic acid (cas: 3903-40-0) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Application In Synthesis of 12-Methoxy-12-oxododecanoic acid
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics