73349-08-3Relevant articles and documents
Role of the CAI-1 fatty acid tail in the Vibrio cholerae quorum sensing response
Perez, Lark J.,Ng, Wai-Leung,Marano, Paul,Brook, Karolina,Bassler, Bonnie L.,Semmelhack, Martin F.
supporting information, p. 9669 - 9681 (2013/01/16)
Quorum sensing is a mechanism of chemical communication among bacteria that enables collective behaviors. In V. cholerae, the etiological agent of the disease cholera, quorum sensing controls group behaviors including virulence factor production and biofilm formation. The major V. cholerae quorum-sensing system consists of the extracellular signal molecule called CAI-1 and its cognate membrane bound receptor called CqsS. Here, the ligand binding activity of CqsS is probed with structural analogues of the natural signal. Enabled by our discovery of a structurally simplified analogue of CAI-1, we prepared and analyzed a focused library. The molecules were designed to probe the effects of conformational and structural changes along the length of the fatty acid tail of CAI-1. Our results, combined with pharmacophore modeling, suggest a molecular basis for signal molecule recognition and receptor fidelity with respect to the fatty acid tail portion of CAI-1. These efforts provide novel probes to enhance discovery of antivirulence agents for the treatment of V. cholerae.
On the conversion of structural analogues of (S)-2-hydroxypropylphosphonic acid to epoxides by the final enzyme of fosfomycin biosynthesis in S. fradiae
Schweifer, Anna,Hammerschmidt, Friedrich
, p. 3056 - 3059 (2008/12/23)
2-Hydroxyethyl- and (S)-2-hydroxybutylphosphonic acid were prepared, starting in the latter case from (S)-2-aminobutyric acid. They were fed to cultures of Streptomyces fradiae producing fosfomycin. Only the latter (150 μg/mL of medium) was converted to the ethyl analogue of fosfomycin, isolated as 2-amino-1-hydroxybutylphosphonic acid (3%) in admixture with 2-amino-1-hydroxypropylphosphonic acid (97%) derived from fosfomycin.
On the interactions of alkyl 2-hydroxycarboxylic acids with alkoxysilanes: Selective esterification of simple 2-hydroxycarboxylic acids
Ansell, Richard J.,Barrett, Simon A.,Meegan, Jonathan E.,Warriner, Stuart L.
, p. 4654 - 4664 (2008/02/08)
The interactions of a range of monocarboxylic acids with tetramethoxysilane Si(OMe)4 (TMOS), in methanol (MeOH), have been investigated by using 1H, 13C and 29Si solution-phase NMR spectroscopy and electrospray mass spectrometry (ESMS). Si(OMe)4 acts as a catalyst/reagent in the selective methylation of 2-hydroxycarboxylic acids (2HOAs) in MeOH at room temperature: glycolic acid, lactic acid and 2-hydroxybutyric acid are esterified more than a hundred times faster in MeOH and Si(OMe)4 than in MeOH alone. No acceleration of methylation is observed for carboxylic acids lacking the 2-hydroxy group. Methylation of the 2HOAs is associated with the condensation of individual siloxane units to form oligomers. A mechanism is proposed in which 2HOAs attach to silicon via the alkoxy group, then subsequently via the carboxyl group in an intramolecular rearrangement to form an unstable and reactive cyclic intermediate. This intermediate may lead to accelerated methylation of the carboxylic acid via nucleophilic attack of MeOH at the carbonyl group, while a separate reaction pathway leads to condensation of silanols and/or alkoxysilanes leading to oligosiloxanes. The mechanism has implications for the use of 2HOAs as templates in sol-gel silica preparation.
