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Original Article

Reduction and cyclization in biotransformation of carbonyl compounds by cultured cells of Taxus species

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Pages 36-44 | Received 25 Mar 2008, Published online: 11 Jul 2009

References

  • Álvarez-Bercedo P, Murga J, Carda M, Marco JA. Stereoselective synthesis of the published structure of feigrisolide A. Structural revision of feigrisolides A and Br J Org Chem 2006; 71: 5766–5769
  • Bradamante S, Ferraccioli R, Pagani GA. The reaction of sodium 1,3-diphenyl-2-azapropenide with 1,2-epoxycyclohexane. J Chem Soc Perkin Trans 1987; I: 515–518
  • Buisson D, Azerad R, Sanner C, Larcheveque M. A study of the stereocontrolled reduction of aliphatic β-ketoesters by Geotrichum candidum. Biocatalysis 1992; 5: 249–265
  • Casas DA, Pitta-Alvarez SI, Giulietti AM. Biotransformation of hydroquinone by hairy root of Brugmansia candida and effect of sugars and free-radical scavengers. Appl Biochem Biotechnol 1998; 69: 127–136
  • Chang M-Y, Chen S-T, Chang N-Ch. A synthesis of racemic thalidomide. Synth Commun 2003; 33: 1375–1382
  • Croteau R, Ketchum REB, Long RM, Kaspera R, Wildung MR. Taxol biosynthesis and molecular genetics. Phytochem Rev 2006; 5: 75–97
  • Eriksson T, Björkman S, Roth B, Fyge Å, Höglund P. Enantiomers of thalidomide: blood distribution and the influence of serum albumin on chiral inversion and hydrolysis. Chirality 1998; 10: 223–228
  • Fadnavis NW, Vadivel SK, Bhalerao UT. Biotransformations with baker's yeast: pH effects on diastereoselectivity during α-hydroxy-β-ketoester reductions and carbon-carbon bond cleavages. Tetrahedron: Asymmetry 1997; 8: 2355–2359
  • Faver IR, Guerra SG, Su WPD, el-Azhary R. Thalidomide for dermatology: a review of clinical uses and adverse effects. Int J Dermatol 2005; 44: 61–67
  • Hamada H, Fuchikami Y, Ikematsu Y, Hirata T, Williams HJ, Scott AI. Hydroxylation of piperitone by cell suspension cultures of Catharanthus roseus. Phytochemistry 1994; 37: 1037–1038
  • Hirata T, Takarada A, Hegazy M-EF, Sato Y, Matsushima A, Kondo Y, Matzuki A, Hamada H. Hydrogenation of the C-C double bond of maleimides with cultured plant cells. J Mol Catal B: Enzym 2005; 32: 131–134
  • Hirata T, Ikeda Y, Izumi S, Shimoda K, Hamada H, Kawamura T. Introduction of oxygenated functional groups into 3-carene and 2-pinene by cultured cells. Phytochemistry 1994; 37: 401–403
  • Ishihara K, Hamada H, Hirata T, Nakajima N. Biotransformation using plant cultured cells. J Mol Catal B: Enzym 2003; 23: 145–170
  • Kamal A, Rao AB, Sattur PB. Enzymatic cyclization of 2-carbamoyloxy benzoates: formation of 2H-1,3-benzoxazine-2,4(3H)-diones. Tetrahedron Lett 1987; 28: 2425–2426
  • Kamal A, Sattur PB. Catalase-mediated cyclization: synthesis of 3-allyl-4-imino substituted 2(1H)-quinazolinones and 1,3-benzoxazine-2(3H)-ones. Tetrahedron Lett 1989; 30: 1133–1134
  • Ketchum REB, Gibson DM. Paclitaxel production in suspension cell cultures of Taxus. Plant Cell Tissue Organ Cult 1996; 46: 9–16
  • Kim J-H, Yun J-H, Hwang Y-S, Byun SY, Kim D-I. Production of Taxol and related taxanes in Taxus brevifolia cell cultures: effect of sugar. Biotechnol Lett 1995; 17: 101–106
  • Kingston DGI, Newman DJ. Taxoids: cancer-fighting compounds from nature. Curr Opin Drug Discovery Devel 2007; 10: 130–144
  • Klivanov AM. Improving enzymes by using them in organic solvents. Nature 2001; 409: 241–246
  • Lee H-Y, An M. Selective 1,4-reduction of unsaturated carbonyl compounds using Co2(CO)8-H2O. Tetrahedron Lett 2003; 44: 2775–2778
  • Linden A, Juch M, Rüedi P. Absolute configuration of 6-O-p-bromobenzoylsalvileucolide methyl ester. Acta Crystallogr Sect C: Cryst Struct Commun 1996; 52: 933–935
  • Ma D, Zhu W. Stereospecific total synthesis of (-)-8-epi-hyperaspine. Tetrahedron Lett 2003; 44: 8609–8612
  • Marques MMB. 2006. Modern methods for asymmetric hydrogenation of ketones. Org Chem Highlights. Available at: http://www.organic-chemistry.org/Highlights/2006/05March.shtm.
  • Marukawa K, Mori K. Synthesis of (1R,3S,5S)-1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene, the male pheromone of a hepialid moth, Endoclita excrescens, and its enantiomer. Eur J Org Chem 2002; 23: 3974–3978
  • Matthews SJ, McCoy C. Thalidomide: a review of approved and investigational uses. Clin Ther 2003; 25: 342–395
  • Miura K, Yamada Y, Tomita M, Hosomi A. Indium (III) acetate-catalyzed 1,4-reduction and reductive aldol reactions of (-enones with phenylsilane. Synlett 2004; 11: 1985–1989
  • Muller GW, Konnecke WE, Smith AM, Khetani VD. A concise two-step synthesis of thalidomide. Org Process Res Dev 1999; 3: 139–140
  • Nakamura K, Yamanaka R, Matsuda T, Harada T. Recent developments in asymmetric reduction of ketones with biocatalysts. Tetrahedron: Asymmetry 2003; 14: 2659–2681
  • Ramos-Lobato NA, Soto-Hernández M, Zavala-Chávez F, Rodríguez-González MT. Taxoides en el follaje del Tejo Mexicano (Taxus globosa Schltdl). Revista Chapingo Serie Horticultura 2003; 9: 29–33
  • Schumacher J, Eckstein M, Kragl U. Influence of water-miscible organic solvents on kinetics and enantioselectivity of the (R)-specific alcohol dehydrogenase from Lactobacillus brevis. Biotechnol J 2006; 1: 574–581
  • Shimoda K, Kwon S, Utsuki A, Ohiwa S, Katsuragi H, Yonemoto N, Hamada H, Hamada H. Glycosylation of capsaicin and 8-nordihydrocapsaicin by cultured cells of Catharanthus roseus. Phytochemistry 2007; 68: 1391–1396
  • Shimoda K, Kubota N, Hamada H, Hamada H. Diastereoselective reduction of (-keto carbonyl compounds by cultured plant cells. Tetrahedron Lett 2006; 47: 1541–1544
  • Suwa T, Nishino K, Miyatake M, Shibata I, Baba A. Synthesis of carbocycles by enone-selective reduction using organoiodotin hydride. Tetrahedron Lett 2000; 41: 3403–3406
  • Takemoto M, Achiwa K. Bioconversion of optically active pyridil alcohols from the corresponding racemates with plant cell cultures. Chem Pharm Bull 1998a; 46: 577–580
  • Takemoto M, Achiwa K. Deracemization of racemic 4-pyridyl-1-ethanol by Catharanthus roseus cell cultures. Phytochemistry 1998b; 49: 1627–1629
  • Toraño JS, Verbon A, Guchelaar H-J. Quantitative determination of thalidomide in human serum with high-performance liquid chromatography using protein precipitation with trichloroacetic acid and ultraviolet detection. J Chromatogr B 1999; 734: 203–210
  • Tumambac GE, Francis CJ, Wolf C. Configurational stability of 2-benzoylcyclohexanone: unexpected solvent effects on the rate of racemization. Chirality 2005; 17: 171–176
  • Wang L-C, Jang H-Y, Roh Y, Lynch V, Schultz AJ, Wang X, Krische MJ. Diastereoselective cycloreductions and cycloadditions catalyzed by Co(dpm)2-silane (dpm = 2,2,6,6-tetramethylheptane-3,5-dionate): mechanism and partitioning of hydrometallative versus anion radical pathways. J Am Chem Soc 2002; 124: 9448–9453
  • Yang L, Dai J, Sakai J, Ando M. Biotransformation of α-santonin by cell suspension cultures of five plants. Biotechnol Lett 2005; 27: 793–797

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