Enantioselective Preparation of δ‐Valerolactones with Horse Liver Alcohol Dehydrogenase

Díaz‐Rodríguez, Alba; Iglésias-Fernández, Javier; Rovira, Carme; Gotor‐Fernández, Vicente

doi:10.1002/cctc.201300640

Cited by 18 publications

(8 citation statements)

References 79 publications

(62 reference statements)

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“…The transformation of 7a was completed within 6 h, which was much faster than that of 8a and 9a (36 h and 72 h) (Table 2, entries 7-9), which suggested that the substrate with larger substituent group binds less efficiently in the active site of enzyme pocket. In terms of product chirality, this catalytic system proceeded with stereoselectivity towards the (S)-enantiomer, which is in accordance with the rule of preferred stereoselectivity of HLADH (Díaz-Rodríguez et al 2014;Kara et al 2013). For the reaction of 7a and 8a, as high as > 95% ee was observed in the present catalytic system (Additional file 1: Figures S12 and S13).…”

Section: Substrate Scope Expandingsupporting

confidence: 85%

Biosynthesis of lactones from diols mediated by an artificial flavin

Zhang

Tan

et al. 2021

Bioresour. Bioprocess.

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Background Lactones are important compounds in the field of medicine, material and chemical industry. One of the promising accesses to these flexible scaffolds is NAD(P)+-dependent alcohol dehydrogenases-catalyzed oxidative lactonization of diols, which relies on the construction of an efficient NAD(P)+ regeneration system. Results In this study, a novel system combining horse liver alcohol dehydrogenase (HLADH) with the synthetic bridged flavin cofactor was established for biosynthesis of lactones. The reaction conditions of this system were optimized and a variety of lactones including chiral lactones were efficiently obtained from various diols. Compared to the previously reported NAD(P)+-regeneration systems, this system showed better regeneration efficiency and product yield. A two-phase system was further applied to solve the problem of product inhibition, and 80% yield was obtained at the condition of 300 mM substrate. Conclusions This study provides an efficient method to synthesis of lactones from diols under mild conditions. We believe this system will be a promising alternative to promote the synthesis of other valuable compounds. Graphic abstract

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Section: Substrate Scope Expandingsupporting

confidence: 85%

Biosynthesis of lactones from diols mediated by an artificial flavin

Zhang

Tan

et al. 2021

Bioresour. Bioprocess.

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“…[110] (HLADH) and other ADHs for the (enantioselective) oxidative lactonisation of various diols. [114] Oxidative lactonisation reactions of diols have also been reported with the laccase-TEMPO system. [115] As the alcohol oxidation step is non-enzymatic,any chiral discrimination can be excluded.…”

Section: Oxidation Of Primary Alcohols To Acidsmentioning

confidence: 99%

Biocatalytic Oxidation Reactions: A Chemist's Perspective

et al. 2018

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Oxidation chemistry using enzymes is approaching maturity and practical applicability in organic synthesis. Oxidoreductases (enzymes catalysing redox reactions) enable chemists to perform highly selective and efficient transformations ranging from simple alcohol oxidations to stereoselective halogenations of non‐activated C−H bonds. For many of these reactions, no “classical” chemical counterpart is known. Hence oxidoreductases open up shorter synthesis routes based on a more direct access to the target products. The generally very mild reaction conditions may also reduce the environmental impact of biocatalytic reactions compared to classical counterparts. In this Review, we critically summarise the most important recent developments in the field of biocatalytic oxidation chemistry and identify the most pressing bottlenecks as well as promising solutions.

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“…epoxide or lactone products. 14,111,112,114,[304][305][306] Furthermore, high product concentrations in easily water separable organic phases will also facilitate DSP (vide infra).…”

Section: How Green/environmentally Friendly Are Biocatalytic Oxyfunctmentioning

confidence: 99%