57602-94-5Relevant articles and documents
Metabolism of deuterated isomeric 6,7-dihydroxydodecanoic acids in Saccharomyces cerevisiae - Diastereo- and enantioselective formation and characterization of 5-hydroxydecano-4-lactone (=4,5-dihydro-5-(1-hydroxyhexyl)furan-2(3H)-one) isomers
Garbe, Leif-A.,Tressl, Roland
, p. 2349 - 2363 (2003)
The chemical synthesis of deuterated isomeric 6,7-dihydroxydodecanoic acid methyl esters 1 and the subsequent metabolism of esters 1 and the corresponding acids 1a in liquid cultures of the yeast Saccharomyces cerevisiae was investigated. Incubation experiments with (6R,7R)- or (6S,7S)-6,7-dihydroxy(6,7-2H2)dodecanoic acid methyl ester ((6R,7R)- or (6S,7S)-(6,7-2H2)-1, resp.) and (±)-threo- or (±)-erythro-6,7-dihydroxy(6,7-2H 2)dodecanoic acid ((±)-threo- or (±)-erythro-(6,7- 2H2)-1a, resp.) elucidated their metabolic pathway in yeast (Tables 1-3). The main products were isomeric 2H-labeled 5-hydroxydecano-4-lactones 2. The absolute configuration of the four isomeric lactones 2 was assigned by chemical synthesis via Sharpless asymmetric dihydroxylation and chiral gas chromatography (Lipodex E). The enantiomers of threo-2 were separated without derivatization on Lipodex E; in contrast, the enantiomers of erythro-2 could be separated only after transformation to their 5-O-(trifluoroacetyl) derivatives. Biotransformation of the methyl ester (6R,7R)-(6,7-2H2)-1 led to (4R,5R)- and (4S,5R)-(2,5- 2H2)-2 (ratio ca. 4:1; Table 2). Estimation of the label content and position of (4S,5R)-(2,5-2H2)-2 showed 95% label at C(5), 68% label at C(2), and no 2H at C(4) (Table 2). Therefore, oxidation and subsequent reduction with inversion at C(4) of 4,5-dihydroxydecanoic acid and transfer of 2H from C(4) to C(2) is postulated. The 5-hydroxydecano-4-lactones 2 are of biochemical importance: during the fermentation of Streptomyces griseus, (4S,5R)-2, known as L-factor, occurs temporarily before the antibiotic production, and (-)-muricatacin (=(4R,5R)-5-hydroxy-heptadecano-4-lactone), a homologue of (4R,5R)-2, is an anticancer agent.
Targeting Staphylococcus aureus quorum sensing with nonpeptidic small molecule inhibitors
Murray, Ewan J.,Crowley, Rebecca C.,Truman, Alex,Clarke, Simon R.,Cottam, James A.,Jadhav, Gopal P.,Steele, Victoria R.,O'Shea, Paul,Lindholm, Catharina,Cockayne, Alan,Chhabra, Siri Ram,Chan, Weng C.,Williams, Paul
supporting information, p. 2813 - 2819 (2014/04/17)
A series of 3-oxo-C12-HSL, tetramic acid, and tetronic acid analogues were synthesized to gain insights into the structural requirements for quorum sensing inhibition in Staphylococcus aureus. Compounds active against agr were noncompetitive inhibitors of the autoinducing peptide (AIP) activated AgrC receptor, by altering the activation efficacy of the cognate AIP-1. They appeared to act as negative allosteric modulators and are exemplified by 3-tetradecanoyltetronic acid 17, which reduced nasal cell colonization and arthritis in a murine infection model.
Iminyl, Amidyl, and Carbamyl Radicals from O-Benzoyl Oximes and O-Benzoyl Hydroxamic Acid Derivatives.
Boivin, Jean,Callier-Dublanchet, Anne-Claude,Quiclet-Sire, Beatrice,Schiano, Anne-Marie,Zard, Samir Z.
, p. 6517 - 6528 (2007/10/02)
Oxime benzoates and O-benzoyl hydroxamic acid derivatives react with tributylstannane in the presence of AIBN to give iminyl, amidyl, and carbamyl radicals which can be captured by an internal olefin.
