Stereoselective biotransformations using fungi as biocatalysts

Borges, Keyller Bastos; Borges, Warley de Souza; Durán-Patrón, Rosa; Pupo, Mônica Tallarico; Bonato, Pierina Sueli; Collado, Isidro González

doi:10.1016/j.tetasy.2009.02.009

Cited by 214 publications

(100 citation statements)

References 145 publications

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“…These findings indicate that acetophenone was converted to phenyl acetate through Baeyer-Villiger oxidation [38] (Fig. 6), which occurs frequently during biotransformations [35][36][37][38][39][40][41][42][43][44]. The reaction is as shown in Fig.…”

Section: Time Course Of Biotransformation Of Acetophenone By C Acutatummentioning

confidence: 96%

Biotransformation of acetophenone to 1-phenylethanol by fungi

Nagaki

Sato

Tanabe

et al. 2016

Trans. Mat. Res. Soc. Japan

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The fungi Botrytis cinerea and Colletotrichum acutatum were used to convert acetophenone to 1-phenylethanol. B. cinerea produced a 98.5% yield of 1-phenylethanol with an enantiomeric excess of 93.8%. Conversely, addition of 1-phenylethanol did not change the reaction rate or product composition. In contrast, the reaction catalyzed by C. acutatum was markedly slower, commencing only after an approximately three-day delay. The concentration of substrate decreased gradually over approximately 14 days, coinciding with increased production of 1-phenylethanol. Phenol was produced after 18 days, and the final yields of 1-phenylethanol and phenol were 38.1% and 61.5%, respectively.

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Section: Time Course Of Biotransformation Of Acetophenone By C Acutatummentioning

confidence: 96%

Biotransformation of acetophenone to 1-phenylethanol by fungi

Nagaki

Sato

Tanabe

et al. 2016

Trans. Mat. Res. Soc. Japan

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“…4 Advantages of using this kind of enzyme transformation include high level of regio-and stereo-selectivity, require mild reaction conditions and are important steps to introduce functional groups into inaccessible sites of the molecules, producing rare structures. [3][4][5][6] The clerodane diterpene (3R, 4S, 5S, 8S, 9R, 10S)-3,12-dioxo-15,16-epoxy-4-hydroxycleroda-13(16),14-diene (1) was isolated for the first time from Croton argyrophylloides (Euphorbiaceae). This compound was biotransformed by Cunninghamella echinulata and Rhizopus stolonifer fungi and produced a new diterpene, as previously described by Monte et al 7 and Mafezoli et al 8 In this work, we report the isolation of one known (B1) and three new diterpenes (B2, B3 and B4) obtained from biotransformation of diterpene 1 by a fungal strain of Lasiodiplodia gonubiensis, Neofusicoccumum ribis and Pseudofusicoccum stromaticum.…”

Section: Introductionmentioning

confidence: 99%

New Clerodane Diterpenes from Fungal Biotransformation of the 3,12-Dioxo-15,16-Epoxy-4-Hydroxycleroda-13(16),14-Diene

Hol¹,

Vasconcelos²,

Barbosa³

et al. 2017

MOJBOC

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Abbreviations: PDA, potato-dextrose agar; DMSO, dimethyl sulfoxide; HPLC-DAD, high performance liquid chromatography--diode array detector; ODS, octadecylsilane; FTIR, fourier transform infrared spectroscopy; HRMS, high-resolution mass spectrometer; 1 HNMR, proton nuclear magnetic resonance;13 CNMR, carbon nuclear magnetic resonance; NOESY, nuclear overhauser effect spectroscopy; HSQC, heteronuclear single quantum coherence; HMBC, heteronuclear multiple bond correlation IntroductionTerpenes, with approximately 30,000 compounds, are considered one of the most important classes of natural products isolated from plants. They have high economic value and have applications in several areas such as pharmaceutical and cosmetic industries. Among the terpenes, diterpenes are notable by exhibiting anti-microbial, insecticidal, anti-carcinogenic, anti-diabetic and neurobiological activities.1-3 Microbial transformations of diterpenes have been reported as an alternative tool to furnish new derivatives. 4 Advantages of using this kind of enzyme transformation include high level of regio-and stereo-selectivity, require mild reaction conditions and are important steps to introduce functional groups into inaccessible sites of the molecules, producing rare structures. [3][4][5][6] The clerodane diterpene (3R, 4S, 5S, 8S, 9R, 10S)-3,12-dioxo-15,16-epoxy-4-hydroxycleroda-13(16),14-diene (1) was isolated for the first time from Croton argyrophylloides (Euphorbiaceae). This compound was biotransformed by Cunninghamella echinulata and Rhizopus stolonifer fungi and produced a new diterpene, as previously described by Monte et al. 7 and Mafezoli et al. 8In this work, we report the isolation of one known (B1) and three new diterpenes (B2, B3 and B4) obtained from biotransformation of diterpene 1 by a fungal strain of Lasiodiplodia gonubiensis, Neofusicoccumum ribis and Pseudofusicoccum stromaticum. Additionally, two new chemical derivatives (Q1 and Q2) obtained by esterification and benzylation of B2. The structures of the diterpenes were established mainly based on their 1D and 2D NMR spectroscopic data and HRMS. Materials and methods General procedureMelting points were determined on a Micro-Quimica MQAPF-302 and Mettler Toledo FP62 apparatus, and are uncorrected. IR spectra were recorded on a Perkin-Elmer Spectrum 100 FT-IR spectrometer. Optical rotations were determined on Jasco P-2000 equipment. NMR spectra were recorded on Bruker Avance DPX 300 (300MHz) and Avance DPX 500 (500MHz) spectrometers. High-resolution MS were obtained on a Shimadzu LC-MS IT-TOF spectrometer equipped with an ESI source in positive and negative modes. Analytical thin-layer chromatography (TLC) was performed on pre-coated 0.25mm thick plates of silica gel 60 F254, and the spots were visualized under a UV lamp (254nm) and by spraying with a solution of perchloric acidvanillin in EtOH, followed by heating. HPLC analyses were done on a Shimadzu instrument equipped with a LC-20AT high-pressure pump, a SPD-M20A photodiode array detector. Potato-dextrose-broth w...

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“…A busca por microrganismos que atuem como produtores de enzimas de degradação de material vegetal tem despertado interesse, visto que esses organismos são capazes de produzir hidrolases extracelulares, como parte do seu mecanismo de resistência para superar as defesas do hospedeiro e/ou para obter nutrientes do solo (BORGES et al, 2009). A enzima xilanase está representada nesse cenário, pois hidrolisa o principal componente da hemicelulose vegetal, a xilana e são comumente utilizadas nas indústrias de papel, alimentos, têxtil, bebidas e ração animal (ADELA et al, 2015).…”

Section: Introductionunclassified