857054-03-6Relevant articles and documents
From Biomass to the Karrikins via Selective Catalytic Oxidation of Hemicellulose-Derived Butyl Xylosides and Glucosides
Slawin, Alexandra M. Z.,Su, Gerard,Westwood, Nicholas,Xiao, Ganyuan
, (2022/02/17)
Members of the karrikin family of bioactive small molecules are known to promote germination of a range of plants following large scale fires. As a result, they are relevant and interesting compounds. This report describes their synthesis from a biomass-derived product stream. During work to fractionate biomass with the goal of obtaining high quality lignins, an interesting co-product stream derived from the hemicellulose in the biomass, was obtained. Whilst many applications of this co-product stream can be proposed, in this case the major monosaccharides have been converted to relevant karrikins in short reaction sequences. Key results include a highly selective catalytic oxidation reaction, conversion of the resulting ketone to a butenolide by two alternative approaches, a selective acetal reductive opening reaction, X-ray crystallographic analysis of two compounds and detailed comparison of the final products with previous literature reports. Only through successful use of all the components generated during biomass refining, can economic sustainability be potentially achieved.
Karrikins from plant smoke modulate bacterial quorum sensing
Mandabi, Aviad,Ganin, Hadas,Krief, Pnina,Rayo, Josep,Meijler, Michael M.
supporting information, p. 5322 - 5325 (2014/05/06)
The discovery that plant smoke contains germination stimuli has led to the identification of a new class of signaling molecules named karrikins. Here we report a potential second role for these molecules: in various bacterial species-A. tumefaciens, P. aeruginosa and V. harveyi-they modulate bacterial quorum-sensing (QS), with very different outcomes. the Partner Organisations 2014.
Synthesis of the germination stimulant 3-methyl-2H-furo[2,3-c]pyran-2-one and analogous compounds from carbohydrates
Goddard-Borger, Ethan D.,Ghisalberti, Emilio L.,Stick, Robert V.
, p. 3925 - 3934 (2008/02/13)
An efficacious synthetic route to the recently identified, potent germination stimulant 3-methyl-2H-furo[2,3-c]pyran-2-one and analogous compounds, using carbohydrate substrates, is described. D-Xylose and D-glucuronic acid γ-lactone were used in the preparation of the parent heterocycle and its 5-methoxycarbonyl analogue, respectively. These compounds were elaborated using various methods to furnish the natural product and a suite of its analogues. The germination stimulant was thus prepared on a multi-gram scale in nine steps from inexpensive, commercially available 1,2-O-isopropylidene-D-xylofuranose in an overall yield of 30 %, vastly improving upon the only method published to date. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
