3063-86-3Relevant articles and documents
Enzymatic Specific Production and Chemical Functionalization of Phenylpropanone Platform Monomers from Lignin
Ohta, Yukari,Hasegawa, Ryoichi,Kurosawa, Kanako,Maeda, Allyn H.,Koizumi, Toshio,Nishimura, Hiroshi,Okada, Hitomi,Qu, Chen,Saito, Kaori,Watanabe, Takashi,Hatada, Yuji
, p. 425 - 433 (2017/02/05)
Enzymatic catalysis is an ecofriendly strategy for the production of high-value low-molecular-weight aromatic compounds from lignin. Although well-definable aromatic monomers have been obtained from synthetic lignin-model dimers, enzymatic-selective synthesis of platform monomers from natural lignin has not been accomplished. In this study, we successfully achieved highly specific synthesis of aromatic monomers with a phenylpropane structure directly from natural lignin using a cascade reaction of β-O-4-cleaving bacterial enzymes in one pot. Guaiacylhydroxylpropanone (GHP) and the GHP/syringylhydroxylpropanone (SHP) mixture are exclusive monomers from lignin isolated from softwood (Cryptomeria japonica) and hardwood (Eucalyptus globulus). The intermediate products in the enzymatic reactions show the capacity to accommodate highly heterologous substrates at the substrate-binding sites of the enzymes. To demonstrate the applicability of GHP as a platform chemical for bio-based industries, we chemically generate value-added GHP derivatives for bio-based polymers. Together with these chemical conversions for the valorization of lignin-derived phenylpropanone monomers, the specific and enzymatic production of the monomers directly from natural lignin is expected to provide a new stream in “white biotechnology” for sustainable biorefineries.
Synthesis of Coniferyl and Dihydroconiferyl Derivatives Using Radical Bromination with N-Bromosuccinimide as the Key Step
Lindeberg, Otto
, p. 15 - 20 (2007/10/02)
Coniferyl and dihydroconiferyl derivatives have been synthesized by reacting bromides, obtained from allylic and benzylic brominations using N-bromosuccinimide (NBS), with appropriate nucleophiles.For instance, NBS bromination of eugenol acetate, followed by replacement of bromine by an acetoxy group and subsequent reduction with lithium aluminium hydride, afforded coniferyl alcohol in 65percent overall yield.Due to the availability of the starting materials (eugenol and isoeugenol) and the good overall yields obtained, these synthetic routes compete well with other methods of preparation.
