246511-74-0Relevant academic research and scientific papers
Biosynthesis of Diverse Antimicrobial and Antiproliferative Acyloins in Anaerobic Bacteria
Schieferdecker, Sebastian,Shabuer, Gulimila,Letzel, Anne-Catrin,Urbansky, Barbara,Ishida-Ito, Mie,Ishida, Keishi,Cyrulies, Michael,Dahse, Hans-Martin,Pidot, Sacha,Hertweck, Christian
, p. 1490 - 1497 (2019)
Metabolic profiling and genome mining revealed that anaerobic bacteria have the potential to produce acyloin natural products. In addition to sattazolin A and B, three new sattazolin congeners and a novel acyloin named clostrocyloin were isolated from three strains of Clostridium beijerinckii, a bacterium used for industrial solvent production. Bioactivity profiling showed that the sattazolin derivatives possess antimicrobial activities against mycobacteria and pseudomonads with only low cytotoxicity. Clostrocyloin was found to be mainly active against fungi. The thiamine diphosphate (ThDP)-dependent sattazolin-producing synthase was identified in silico and characterized both in vivo and in in vitro enzyme assays. A related acyloin synthase from the clostrocyloin producer was shown to be responsible for the production of the acyloin core of clostrocyloin. The biotransformation experiments provided first insights into the substrate scope of the clostrocyloin synthase and revealed biosynthetic intermediates.
Synthesis of α-hydroxy ketones and vicinal (R, R)-diols by Bacillus clausii DSM 8716T butanediol dehydrogenase
Bongaerts, Johannes,Jablonski, Melanie,Kipp, Carina Ronja,Molinnus, Denise,Muschallik, Lukas,Pohl, Martina,Sch?ning, Michael J.,Selmer, Thorsten,Siegert, Petra,Wagner, Torsten
, p. 12206 - 12216 (2020/04/20)
α-hydroxy ketones (HK) and 1,2-diols are important building blocks for fine chemical synthesis. Here, we describe the R-selective 2,3-butanediol dehydrogenase from B. clausii DSM 8716T (BcBDH) that belongs to the metal-dependent medium chain dehydrogenases/reductases family (MDR) and catalyzes the selective asymmetric reduction of prochiral 1,2-diketones to the corresponding HK and, in some cases, the reduction of the same to the corresponding 1,2-diols. Aliphatic diketones, like 2,3-pentanedione, 2,3-hexanedione, 5-methyl-2,3-hexanedione, 3,4-hexanedione and 2,3-heptanedione are well transformed. In addition, surprisingly alkyl phenyl dicarbonyls, like 2-hydroxy-1-phenylpropan-1-one and phenylglyoxal are accepted, whereas their derivatives with two phenyl groups are not substrates. Supplementation of Mn2+ (1 mM) increases BcBDH's activity in biotransformations. Furthermore, the biocatalytic reduction of 5-methyl-2,3-hexanedione to mainly 5-methyl-3-hydroxy-2-hexanone with only small amounts of 5-methyl-2-hydroxy-3-hexanone within an enzyme membrane reactor is demonstrated.
Synthesis of 2-hydroxy-5-methyl-3-hexanone
Tian, Hong-Yu,Ye, Hong-Lin,Sun, Bao-Guo,Wang, Ya-Ling
, p. 51 - 52 (2011/05/07)
2-Hydroxy-5-methyl-3-hexanone, which is a characteristic component of eucalyptus honeys, was synthesised by oxidation of the silyl enol ether of 5-methyl-3-hexanone. 5-Methyl-3-hexanone was prepared by Grignard reaction and oxidation starting from isovaleraldehyde and ethylmagnesium bromide. The desired silyl enol ether was produced with high selectivity by deprotonation of 5-methyl-3-hexanone with NaHMDS in n-hexane followed by reaction with chlorotrimethylsilane and then oxidised by MCPBA to give pure 2-hydroxy-5-methyl-3-hexanone in about 77% yield after purification by flash chromatography. 2-Hydroxy-5-methyl-3-hexanone has a cheese and sour milk odour.
Hydroxy-methyl-hexanones as flavoring agents
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, (2008/06/13)
The present invention relates to new alpha -hydroxyketone compositions. In particular, there is provided 3-hydroxy-5-methyl-hexan-2-one, 2-hydroxy-5-methyl-hexan-3-one and mixtures thereof. These compounds have utility as flavoring and masking agents for, e.g., food and beverages. Processes for making such compounds also are provided.
