Abstract
Microbial transformation of 13β-alkyl-3-methoxy-8, 14, secogona-1, 3, 5(10), 9-tetraen-14, 17-dion with Saccharomyces cerevisiae resulted in two metabolites: product 1 (P1) and product 2 (P2). Among these, P1 was identified to be 13β alkyl-3-methoxy-8, 14-seco-1, 3, 5(10), 9(11)-estratetraene-17β-ol, 14-one, which has been studied extensively. P2 was purified, crystallized, and identified as 13β-alkyl-3-methoxy-8, 14, secogona-1, 3, 5(10), 9-tetraen-14, 17-diol by X-ray single crystal diffraction method. It was first reported in fermentation medium and the dihydroxyl reduction is a new reaction in biotransformation of steroid.
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References
Chen DJ, Zhu BQ (2006) Application of microbial transformation in modern pharmaceutical industry. Chin J Antibiot 31(2):112–118
Wang X, Xu W, You S (2006) Application of microbialtransformation in pharmacology. J Shenyang Pharm Univ 7(23):477–482
Murray HC, Peterson DH (1952) Eoxygenation of steriod by muoorales fungi. US Patent 2602729
Manosroi J, Abe M, Manosroi A (1999) Biotransformation of steroidal drugs using microorganisms screened from various sites in Chiang Mai, Thailand. Bioresour Technol 69(1):67–73
Venkataraman S, Roy RK, Chadha A (2013) Asymmetric reduction of alkyl-3-oxobutanoates by Candida parapsilosis ATCC 7330: insights into solvent and substrate optimisation of the biocatalytic reaction. Appl Biochem Biotechnol 171(3):756–770
Bhuniya R, Nanda S (2011) Asymmetric synthesis of the active form of loxoprofen and its analogue. Tetrahedron Asymmetry 22(10):1125–1132
Bihari V, Joshi AK, Khan AW (1985) Biotransformation of 3-methoxy-8, 14-seco-1, 3, 5(10), 9(11) estratetraen-14, 17-dione (secodione) to its 17β-hydroxy derivative (secol) using immobilized yeast cells (Pichia farinosa Y-118). Biotechnol Bioeng 27(9):1347–1352
Nara M, Terashima S, Yamada S (1980) Stereochemical studies-LVIII: synthesis of optically active compounds by the novel use of meso-compound-2.1 efficient synthesis of an optically pure steroid intermediate. Tetrahedron 36(22):3171–3175
Tomorkeny E, Makk N, Toth G et al (1976) Some 13β-alkyl-3-Methoxy-8, 14-secoestra-1, 3, 5(10), 9-gonatetraene derivatives. Ι. Synthesis of 14, 17-dihydroxy derivatives. Acta Chimica Academiae Scientiarum Hungaricae 91(1):81–90
Fa YH, Xu SW, Ma SH (1978) Studies on the microbiologucal preparation of 13β ethyl-3-methoxy-8, 14-seco-1, 3, 5(10), 9(11)-estratetraene-17β-ol, 14-one. Acta Microbiol 18(3):232–238
Kosmol H, Kieslich K, Vössing R et al (1967) Totalsynthese optisch aktiver Steroide, I. Mikrobiologische stereospezifische Reduktion von 3-Methoxy-8, 14-seco-1, 3, 5(10), 9-östratetraen-14, 17-dion. Liebigs Ann Chem 701(1):198–205
Acknowledgments
This work was supported financially by Natural Science Foundation of China (No. 21206127) and Applied Basic Research Programs of Science and Technology Commission Foundation of Tianjin (No.12JCQNJC06400).
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Yu, L., Mao, S., Ji, S., Liu, X., Lu, F. (2015). Reduction Reaction of Methyl Condensation Compound by Saccharomyces cerevisiae . In: Zhang, TC., Nakajima, M. (eds) Advances in Applied Biotechnology. Lecture Notes in Electrical Engineering, vol 332. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-45657-6_37
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DOI: https://doi.org/10.1007/978-3-662-45657-6_37
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