589-98-0Relevant articles and documents
Biocatalytic synthesis of non-vicinal aliphatic diols
Ebrecht, Ana C.,Aschenbrenner, Jasmin C.,Smit, Martha S.,Opperman, Diederik J.
supporting information, p. 439 - 445 (2021/01/29)
Biocatalysts are receiving increased attention in the field of selective oxyfunctionalization of C-H bonds, with cytochrome P450 monooxygenases (CYP450s), and the related peroxygenases, leading the field. Here we report on the substrate promiscuity of CYP505A30, previously characterized as a fatty acid hydroxylase. In addition to its regioselective oxyfunctionalization of saturated fatty acids (ω-1-ω-3 hydroxylation), primary fatty alcohols are also accepted with similar regioselectivities. Moreover, alkanes such as n-octane and n-decane are also readily accepted, allowing for the production of non-vicinal diols through sequential oxygenation. This journal is
Facile Stereoselective Reduction of Prochiral Ketones by using an F420-dependent Alcohol Dehydrogenase
Martin, Caterina,Tjallinks, Gwen,Trajkovic, Milos,Fraaije, Marco W.
, p. 156 - 159 (2020/10/26)
Effective procedures for the synthesis of optically pure alcohols are highly valuable. A commonly employed method involves the biocatalytic reduction of prochiral ketones. This is typically achieved by using nicotinamide cofactor-dependent reductases. In this work, we demonstrate that a rather unexplored class of enzymes can also be used for this. We used an F420-dependent alcohol dehydrogenase (ADF) from Methanoculleus thermophilicus that was found to reduce various ketones to enantiopure alcohols. The respective (S) alcohols were obtained in excellent enantiopurity (>99 % ee). Furthermore, we discovered that the deazaflavoenzyme can be used as a self-sufficient system by merely using a sacrificial cosubstrate (isopropanol) and a catalytic amount of cofactor F420 or the unnatural cofactor FOP to achieve full conversion. This study reveals that deazaflavoenzymes complement the biocatalytic toolbox for enantioselective ketone reductions.
Application of new Ru (II) pyridine-based complexes in the partial oxidation of n-octane
Chanerika, Revana,Friedrich, Holger B.,Shozi, Mzamo L.
, (2019/12/24)
Tridentate and bidentate Ru (II) complexes were prepared through reaction of four pyridine-based ligands: pyCH2N(R)CH2py {R = propyl, tert-butyl, cyclohexyl and phenyl; py = pyridine} with the [(η6-C6H6)Ru(μ-Cl)Cl]2 dimer. Crystal structures of the new terdentate Ru (II) complexes [Ru{pyCH2N(R)CH2py}C6H6](PF6)2 (R = C3H7 (1), C (CH3)3 (2), C6H11 (3) and the bidentate Ru (II) complex [Ru{pyCH2N(R)}C6H6]PF6 (R = C6H5 (4)) are reported. It was found that complexes 1, 2, 3 and 4 crystallised as mono-metallic species, with a piano stool geometry around each Ru centre. All complexes were active in the selective oxidation of n-octane using t-BuOOH and H2O2 as oxidants. Complexes 2 and 4 reached a product yield of 12% with t-BuOOH as oxidant, however, superior yields (23–32%) were achieved using H2O2 over all systems. The selectivity was predominantly towards alcohols (particularly 2-octanol) over all complexes using t-BuOOH and H2O2 after reduction of the formed alkylhydroperoxides in solution by PPh3. High TONs of up to 2400 were achieved over the Ru/H2O2 systems.