30414-54-1Relevant articles and documents
Synthesis of a biotin-labeled quorum-sensing molecule: Towards a general method for target identification
Spandl, Richard J.,Nicholson, Rebecca L.,Marsden, David M.,Hodgkinson, James T.,Su, Xianbin,Thomas, Gemma L.,Salmond, George P. C.,Welch, Martin,Spring, David R.
, p. 2122 - 2126 (2008)
The synthesis of bacterial quorum-sensing regulator N- (3-oxohexanoyl)-L- homoserine lactone (OHHL) and biotin-tagged OHHL is reported. The latter will be applied to developing a general method to address the 'target identification problem' in chemical genetics. Georg Thieme Verlag Stuttgart.
Metabolites of the Anaerobic Degradation of n-Hexane by Denitrifying Betaproteobacterium Strain HxN1
Küppers, Julian,Mitschke, Nico,Heyen, Simone,Rabus, Ralf,Wilkes, Heinz,Christoffers, Jens
, p. 373 - 380 (2019/11/19)
The constitutions of seven metabolites formed during anaerobic degradation of n-hexane by the denitrifying betaproteobacterium strain HxN1 were elucidated by comparison of their GC and MS data with those of synthetic reference standards. The synthesis of 4-methyloctanoic acid derivatives was accomplished by the conversion of 2-methylhexanoyl chloride with Meldrum's acid. The β-oxoester was reduced with NaBH4, the hydroxy group was eliminated, and the double bond was displaced to yield the methyl esters of 4-methyl-3-oxooctanoate, 3-hydroxy-4-methyloctanoate, (E)-4-methyl-2-octenoate, and (E)- and (Z)-4-methyl-3-octenoate. The methyl esters of 2-methyl-3-oxohexanoate and 3-hydroxy-2-methylhexanoate were similarly prepared from butanoyl chloride and Meldrum's acid. However, methyl (E)-2-methyl-2-hexenoate was prepared by Horner–Wadsworth–Emmons reaction, followed by isomerization to methyl (E)-2-methyl-3-hexenoate. This investigation, with the exception of 4-methyl-3-oxooctanoate, which was not detectable in the cultures, completes the unambiguous identification of all intermediates of the anaerobic biodegradation of n-hexane to 2-methyl-3-oxohexanoyl coenzyme A (CoA), which is then thiolytically cleaved to butanoyl-CoA and propionyl-CoA; these two metabolites are further transformed according to established pathways.
Isolation of the antibiotic pseudopyronine B and SAR evaluation of C3/C6 alkyl analogs
Bouthillette, Leah M.,Darcey, Catherine A.,Handy, Tess E.,Seaton, Sarah C.,Wolfe, Amanda L.
supporting information, p. 2762 - 2765 (2017/05/29)
Natural products are an abundant source of structurally diverse compounds with antibacterial activity that can be used to develop new and potent antibiotics. One such class of natural products is the pseudopyronines. Here we present the isolation of pseudopyronine B (2) from a Pseudomonas species found in garden soil in Western North Carolina, and SAR evaluation of C3 and C6 alkyl analogs of the natural product for antibacterial activity against Gram-positive and Gram-negative bacteria. We found a direct relationship between antibacterial activity and C3/C6 alkyl chain length. For inhibition of Gram-positive bacteria, alkyl chain lengths between 6 and 7 carbons were found to be the most active (IC50?=?0.04–3.8?μg/mL) whereas short alkyl chain analogs showed modest activity against Gram-negative bacteria (IC50?=?223–304?μg/mL). This demonstrates the potential for this class of natural products to be optimized for selective activity against either Gram-positive or Gram-negative bacteria.
