Kadirvel Manikandan, Stimpson William T, Moumene-Afifi Souad, Arsic Biljana, Glynn Nicola, Halliday Nigel, Williams Paul, Gilbert Peter, McBain Andrew J, Freeman Sally, Gardiner John M
School of Pharmacy and Pharmaceutical Sciences, University of Manchester, Manchester M13 9PT, UK.
Bioorg Med Chem Lett. 2010 Apr 15;20(8):2625-8. doi: 10.1016/j.bmcl.2010.02.064. Epub 2010 Feb 19.
The autoinducer (4S)-4,5-dihydroxypentane-2,3-dione ((S)-DPD, AI-2) facilitates chemical communication, termed 'quorum sensing', amongst a wide range of bacteria, The synthesis of (S)-DPD is challenging in part due to its instability. Herein we report a novel synthesis of (S)-DPD via (2S)-2,3-O-isopropylidene glyceraldehyde, through Wittig, dihydroxylation and oxidation reactions, with a complimentary asymmetric synthesis to a key precursor. Its enantiomer (R)-DPD, was prepared from d-mannitol via (2R)-2,3-O-isopropylideneglyceraldehyde. The synthesized enantiomers of DPD have AI-2 bioluminescence-inducing properties in the Vibrio harveyi BB170 strain.
自诱导物（4S）-4,5-二羟基戊烷-2,3-二酮（（S）-DPD，AI-2）促进了多种细菌之间的化学通讯，即“群体感应”。（S）-DPD的合成具有挑战性，部分原因是其不稳定性。在此，我们报道了一种通过（2S）-2,3-O-异亚丙基甘油醛，经维蒂希反应、二羟基化反应和氧化反应，对关键前体进行互补不对称合成来制备（S）-DPD的新方法。其对映体（R）-DPD由d-甘露糖醇经（2R）-2,3-O-异亚丙基甘油醛制备。合成的DPD对映体在哈维弧菌BB170菌株中具有AI-2生物发光诱导特性。
