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IJSTR >> Volume 8 - Issue 10, October 2019 Edition



International Journal of Scientific & Technology Research  
International Journal of Scientific & Technology Research

Website: http://www.ijstr.org

ISSN 2277-8616



Stereo-Selective Bio-Reduction Of Acetophenone And Its Derivatives By Soil Fungal Isolates

[Full Text]

 

AUTHOR(S)

Saravanan. J, Suneetha. V

 

KEYWORDS

Bio-reduction, Acetophenone, Penicillium sp., Aspergillus sp., Biotransformation.

 

ABSTRACT

Microbial asymmetric reduction of ketone is an efficient tool for the synthesis of chiral alcohols. Many reports are available for the bio-reduction of acetophenone and its derivatives, since it is widely used model substrate. This research focus on exploring the soil fungal isolates for their ability towards the reduction of acetophenone and its derivatives to their corresponding chiral alcohols using growing cells instead of resting cells. Bio-reduction of acetophenone, 4-fluoro acetophenone, and 4-chloro acetophenone were carried out using different fungal cultures isolated from soil. All the isolates exhibited a good reduction capability when grown in an optimal condition. Among the screened fungal cultures, Penicillium sp. and Aspergillus sp. showed significant bioconversion with varying enantio-selectivity. However, the Penicillium sp. has showed maximum ability of bio-reduction. The best performing isolate was characterized using internal transcribed spacer (ITS) region and found to be Penicillium rubens VIT SS1, which showed higher conversion and selectivity more than 90% towards acetophenone and its derivatives. The reaction conditions such as pH, temperature and media were evaluated for the bio-reduction of acetophenone using Penicillium rubens VIT SS1. The substrate loading was increased from 0.5g/L to 6g/L at shake flask level using the optimized condition pH 5±0.5 and temperature 25±2°C. This study revealed huge potential of fungal cultures for the synthesis of many aromatic chiral alcohols in a simpler, novel and cost effective manner.

 

REFERENCES

[1] Borges KB, Borges W de S, Durán-Patrón R, Pupo MT, Bonato PS, Collado IG. Stereoselective biotransformations using fungi as biocatalysts. Tetrahedron: Asymmetry 2009; 20:385–97. doi:10.1016/j.tetasy.2009.02.009.
[2] Goswami A, Bezbaruah R., Goswami J, Borthakur N, Dey D, Hazarika A. Microbial reduction of ω-bromoacetophenones in the presence of surfactants. Tetrahedron: Asymmetry 2000;11:3701–9. doi: 10.1016/S0957-4166(00)00341-4.
[3] Kuncham R, Gurumurthy KT, Chandan N, Javed A, Ashwini LS, Shenoi R, et al. Biocatalytic Ketone Reduction - A Study on Screening and Effect of Culture Conditions on the Reduction of Selected Ketones. International Letters of Natural Sciences 2013;6:54–77. doi:10.18052/www.scipress.com/ILNS.6.54.
[4] Goldberg K, Schroer K, Lütz S, Liese A. Biocatalytic ketone reduction—a powerful tool for the production of chiral alcohols—part I: processes with isolated enzymes. Applied Microbiology and Biotechnology 2007; 76:237–48. Doi: 10.1007/s00253-007-1002-0.
[5] Patel RN, Goswami A, Chu L, Donovan MJ, Nanduri V, Goldberg S, et al. Enantioselective microbial reduction of substituted acetophenones. Tetrahedron: Asymmetry 2004;15:1247–58. doi:10.1016/j.tetasy.2004.02.024.
[6] Kurbanoglu EB, Zilbeyaz K, Kurbanoglu NI, Kilic H. Enantioselective Reduction of Substituted Acetophenones by Aspergillus niger. ChemInform 2007;38. doi:10.1002/chin.200745066.
[7] Nakamura K, Yamanaka R, Matsuda T, Harada T. Recent developments in asymmetric reduction of ketones with biocatalysts. Tetrahedron: Asymmetry 2003;14:2659–81. doi:10.1016/S0957-4166(03)00526-3.
[8] Kurbanoglu EB, Zilbeyaz K, Ozdal M, Taskin M, Kurbanoglu NI. Asymmetric reduction of substituted acetophenones using once immobilized Rhodotorula glutinis cells. Bioresource Technology 2010; 101:3825–9. doi:10.1016/j.biortech.2010.01.016.
[9] Rocha LC, Ferreira HV, Pimenta EF, Berlinck RGS, Seleghim MHR, Javaroti DCD, et al. Bioreduction of α-chloroacetophenone by whole cells of marine fungi. Biotechnology Letters 2009; 31:1559–63. Doi: 10.1007/s10529-009-0037-y.
[10] Kurbanoglu EB, Zilbeyaz K, Kurbanoglu NI, Taskin M. Highly enantioselective reduction of acetophenone by locally isolated Alternaria alternata using ram horn peptone. Tetrahedron: Asymmetry 2007; 18:1529–32. doi:10.1016/j.tetasy.2007.06.013.
[11] Saravanan J, Suneetha V. Asymmetric synthesis of chiral alcohols for API production using microorganisms-A mini review. Research Journal of Pharmacy and Technology 2017; 10:1881. doi:10.5958/0974-360X.2017.00330.4.
[12] Patel RN, Goswami A, Chu L, Nanduri V, Goldberg S, Johnston R, et al. Stereoselective reduction of substituted acetophenone, 2004.
[13] Farid Toma, Nareen Abdulla. Isolation, Identification and Seasonal Distribution of Soilborne Fungi in Different Areas of Erbil Governorate. Jalrb 2012; 3.
[14] Parkinson D, Williams ST. A method for isolating fungi from soil microhabitats. Plant and Soil 1960; 13:347–55. Doi: 10.1007/BF01394646.
[15] Warcup JH. On the origin of colonies of fungi developing on soil dilution plates. Transactions of the British Mycological Society 1955; 38:298–301. Doi: 10.1016/S0007-1536(55)80075-7.
[16] Martin JP. Use of acid, rose bengal, and streptomycin in the plate method for estimating soil fungi: Soil Science 1950; 69:215–32. Doi: 10.1097/00010694-195003000-00006.
[17] Elad Y, Chet I, Henis Y. A selective medium for improving quantitative isolation of Trichoderma spp. from soil. Phytoparasitica 1981; 9:59–67. Doi: 10.1007/BF03158330.
[18] More GV, Badgujar KC, Bhanage BM. Kinetic resolution of secondary alcohols with Burkholderia cepacia lipase immobilized on a biodegradable ternary blend polymer matrix as a highly efficient and heterogeneous recyclable biocatalyst. RSC Advances 2015; 5:4592–8. Doi: 10.1039/C4RA14478C.
[19] Lee SB, Milgroom MG, Taylor JW. A rapid, high yield mini-prep method for isolation of total genomic DNA from fungi. Fungal Genetics Reports 1988; 35:23. doi:10.4148/1941-4765.1531.
[20] Wu Y, Guan K, Wang Z, Xu B, Zhao F. Isolation, Identification and Characterization of an Electrogenic Microalgae Strain. PLoS ONE 2013; 8:e73442. doi:10.1371/journal.pone.0073442.
[21] Tendulkar SR, Gupta A, Chattoo BB. A simple protocol for isolation of fungal DNA. Biotechnology Letters 2003; 25:1941–4. doi:10.1023/B:BILE.0000003990.27624.04.
[22] Soni.P. Banerjee, U.C. Enantioselective reduction of acetophenone and its derivatives with new yeast isolate Candida tropiclais PBR-2 MTCC 5158. Biotechnology 1, 80-85. 2006.
[23] Saitou N. and Nei M. The neighbor-joining method: A new method for reconstructing phylogenetic trees. Molecular Biology and Evolution 4:406-425, 1987.
[24] Felsenstein J. Confidence limits on phylogenies: An approach using the bootstrap. Evolution 39:783-791, 1985.
[25] Tamura K., Nei M., and Kumar S. Prospects for inferring very large phylogenies by using the neighbor-joining method. Proceedings of the National Academy of Sciences (USA) 101:11030-11035, 2004.
[26] Kumar S., Stecher G., Li M., Knyaz C., and Tamura K. MEGA X: Molecular Evolutionary Genetics Analysis across computing platforms. Molecular Biology and Evolution 35:1547-1549, 2018.
[27] Li H, Li Z, Ruan G, et al. Asymmetric reduction of acetophenone into R-(+)-1-phenylethanol by endophytic fungus Neofusicoccum parvum BYEF07 isolated from Illicium verum. Biochemical and Biophysical Research Communications 473:874–878. Doi: 10.1016/j.bbrc.2016.03. 142, 2016.
[28] Nakamura K, Matsuda T. Biocatalytic Reduction of Carbonyl Groups. Current Organic Chemistry 10:1217–1246. doi: 10.2174/138527206777698020, 2006.