메뉴 건너뛰기




Volumn 27, Issue 1, 2009, Pages 36-44

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

Author keywords

2 benzoylcyclohexanone; Biocyclization; Bioreduction; Cell cultures; Ethyl acetoacetate; N phthaloyl L glutamine; Taxus brevifolia; Taxus globosa; Thalidomide

Indexed keywords

AMINO ACIDS; CARBONYLATION;

EID: 58049202889     PISSN: 10242422     EISSN: 10292446     Source Type: Journal    
DOI: 10.1080/10242420802475811     Document Type: Article
Times cited : (3)

References (39)
  • 1
    • 33746342163 scopus 로고    scopus 로고
    • Stereoselective synthesis of the published structure of feigrisolide A. Structural revision of feigrisolides
    • Alvarez-Bercedo, P., Murga, J., Carda, M. and Marco, JA. (2006) Stereoselective synthesis of the published structure of feigrisolide A. Structural revision of feigrisolides A and Br J Org Chem, 71, pp. 5766-5769.
    • (2006) A and Br J Org Chem , vol.71 , pp. 5766-5769
    • Alvarez-Bercedo, P.1    Murga, J.2    Carda, M.3    Marco, J.A.4
  • 2
    • 37049086120 scopus 로고
    • The reaction of sodium 1,3-diphenyl-2-azapropenide with 1,2-epoxycyclohexane
    • Bradamante, S., Ferraccioli, R. and Pagani, GA. (1987) The reaction of sodium 1,3-diphenyl-2-azapropenide with 1,2-epoxycyclohexane. J Chem Soc Perkin Trans, pp. 515-518.
    • (1987) J Chem Soc Perkin Trans , pp. 515-518
    • Bradamante, S.1    Ferraccioli, R.2    Pagani, G.A.3
  • 3
    • 84907036080 scopus 로고
    • A study of the stereocontrolled reduction of aliphatic β-ketoesters by Geotrichum candidum
    • Buisson, D., Azerad, R., Sanner, C. and Larcheveque, M. (1992) A study of the stereocontrolled reduction of aliphatic β-ketoesters by Geotrichum candidum. Biocatalysis, 5, pp. 249-265.
    • (1992) Biocatalysis , vol.5 , pp. 249-265
    • Buisson, D.1    Azerad, R.2    Sanner, C.3    Larcheveque, M.4
  • 4
    • 0031851357 scopus 로고    scopus 로고
    • Biotransformation of hydroquinone by hairy root of Brugmansia candida and effect of sugars and free-radical scavengers
    • Casas, DA, Pitta-Alvarez, SI and Giulietti, AM. (1998) Biotransformation of hydroquinone by hairy root of Brugmansia candida and effect of sugars and free-radical scavengers. Appl Biochem Biotechnol, 69, pp. 127-136.
    • (1998) Appl Biochem Biotechnol , vol.69 , pp. 127-136
    • Casas, D.A.1    Pitta-Alvarez, S.I.2    Giulietti, A.M.3
  • 5
    • 0038303230 scopus 로고    scopus 로고
    • A synthesis of racemic thalidomide
    • Chang, M-Y, Chen, S-T and Chang, N-Ch. (2003) A synthesis of racemic thalidomide. Synth Commun, 33, pp. 1375-1382.
    • (2003) Synth Commun , vol.33 , pp. 1375-1382
    • Chang, M.-Y.1    Chen, S.-T.2    Chang, N.-Ch.3
  • 7
    • 0345191687 scopus 로고    scopus 로고
    • Enantiomers of thalidomide: Blood distribution and the influence of serum albumin on chiral inversion and hydrolysis
    • Eriksson, T., Bjorkman, S., Roth, B., Fyge, Å and Hoglund, P. (1998) Enantiomers of thalidomide: Blood distribution and the influence of serum albumin on chiral inversion and hydrolysis. Chirality, 10, pp. 223-228.
    • (1998) , pp. 223-228
    • Eriksson, T.1    Bjorkman, S.2    Roth, B.3    Fyge, Å.4    Hoglund, P.5
  • 8
    • 0343554078 scopus 로고    scopus 로고
    • Biotransformations with baker's yeast: pH effects on diastereoselectivity during α-hydroxy-β-ketoester reductions and carbon-carbon bond cleavages
    • Fadnavis, NW, Vadivel, SK and Bhalerao, UT. (1997) Biotransformations with baker's yeast: pH effects on diastereoselectivity during α-hydroxy-β-ketoester reductions and carbon-carbon bond cleavages. Tetrahedron: Asymmetry, 8, pp. 2355-2359.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 2355-2359
    • Fadnavis, N.W.1    Vadivel, S.K.2    Bhalerao, U.T.3
  • 9
    • 13444273505 scopus 로고    scopus 로고
    • Thalidomide for dermatology: A review of clinical uses and adverse effects
    • Faver, IR, Guerra, SG, Su, WPD and el-Azhary, R. (2005) Thalidomide for dermatology: A review of clinical uses and adverse effects. Int J Dermatol, 44, pp. 61-67.
    • (2005) Int J Dermatol , vol.44 , pp. 61-67
    • Faver, I.R.1    Guerra, S.G.2    Su, W.P.D.3    el-Azhary, R.4
  • 12
    • 0028500575 scopus 로고
    • Introduction of oxygenated functional groups into 3-carene and 2-pinene by cultured cells
    • Hirata, T., Ikeda, Y., Izumi, S., Shimoda, K., Hamada, H. and Kawamura, T. (1994) Introduction of oxygenated functional groups into 3-carene and 2-pinene by cultured cells. Phytochemistry, 37, pp. 401-403.
    • (1994) Phytochemistry , vol.37 , pp. 401-403
    • Hirata, T.1    Ikeda, Y.2    Izumi, S.3    Shimoda, K.4    Hamada, H.5    Kawamura, T.6
  • 14
    • 18744382627 scopus 로고
    • Enzymatic cyclization of 2-carbamoyloxy benzoates: Formation of 2H-1,3-benzoxazine-2,4(3H)-diones
    • Kamal, A., Rao, AB and Sattur, PB. (1987) Enzymatic cyclization of 2-carbamoyloxy benzoates: Formation of 2H-1,3-benzoxazine-2,4(3H)-diones. Tetrahedron Lett, 28, pp. 2425-2426.
    • (1987) Tetrahedron Lett , vol.28 , pp. 2425-2426
    • Kamal, A.1    Rao, A.B.2    Sattur, P.B.3
  • 15
    • 0024560726 scopus 로고
    • Catalase-mediated cyclization: Synthesis of 3-allyl-4-imino substituted 2(1H)-quinazolinones and 1,3-benzoxazine-2(3H)-ones
    • Kamal, A. and Sattur, PB. (1989) Catalase-mediated cyclization: synthesis of 3-allyl-4-imino substituted 2(1H)-quinazolinones and 1,3-benzoxazine-2(3H)-ones. Tetrahedron Lett, 30, pp. 1133-1134.
    • (1989) Tetrahedron Lett , vol.30 , pp. 1133-1134
    • Kamal, A.1    Sattur, P.B.2
  • 16
    • 0030468507 scopus 로고    scopus 로고
    • Paclitaxel production in suspension cell cultures of Taxus
    • Ketchum, REB and Gibson, DM. (1996) Paclitaxel production in suspension cell cultures of Taxus. Plant Cell Tissue Organ Cult, 46, pp. 9-16.
    • (1996) Plant Cell Tissue Organ Cult , vol.46 , pp. 9-16
    • Ketchum, R.E.B.1    Gibson, D.M.2
  • 17
    • 0028904573 scopus 로고
    • Production of Taxol and related taxanes in Taxus brevifolia cell cultures: Effect of sugar
    • Kim, J-H, Yun, J-H, Hwang, Y-S, Byun, SY and Kim, D-I. (1995) Production of Taxol and related taxanes in Taxus brevifolia cell cultures: Effect of sugar. Biotechnol Lett, 17, pp. 101-106.
    • (1995) Biotechnol Lett , vol.17 , pp. 101-106
    • Kim, J.-H.1    Yun, J.-H.2    Hwang, Y.-S.3    Byun, S.Y.4    Kim, D.-I.5
  • 19
    • 0035843166 scopus 로고    scopus 로고
    • Improving enzymes by using them in organic solvents
    • Klivanov, AM. (2001) Improving enzymes by using them in organic solvents. Nature, 409, pp. 241-246.
    • (2001) Nature , vol.409 , pp. 241-246
    • Klivanov, A.M.1
  • 20
    • 0037474679 scopus 로고    scopus 로고
    • Selective 1,4-reduction of unsaturated carbonyl compounds using Co2(CO)8-H2O
    • Lee, H-Y and An, M. (2003) Selective 1,4-reduction of unsaturated carbonyl compounds using Co2(CO)8-H2O. Tetrahedron Lett, 44, pp. 2775-2778.
    • (2003) Tetrahedron Lett , vol.44 , pp. 2775-2778
    • Lee, H.-Y.1    An, M.2
  • 21
    • 0030122762 scopus 로고    scopus 로고
    • Absolute configuration of 6-O-p-bromobenzoylsalvileucolide methyl ester
    • Linden, A., Juch, M. and Ruedi, P. (1996) Absolute configuration of 6-O-p-bromobenzoylsalvileucolide methyl ester. Acta Crystallogr Sect C: Cryst Struct Commun, 52, pp. 933-935.
    • (1996) Acta Crystallogr Sect C: Cryst Struct Commun , vol.52 , pp. 933-935
    • Linden, A.1    Juch, M.2    Ruedi, P.3
  • 22
    • 0142138293 scopus 로고    scopus 로고
    • Stereospecific total synthesis of (-)-8-epi-hyperaspine
    • Ma, D. and Zhu, W. (2003) Stereospecific total synthesis of (-)-8-epi-hyperaspine. Tetrahedron Lett, 44, pp. 8609-8612.
    • (2003) Tetrahedron Lett , vol.44 , pp. 8609-8612
    • Ma, D.1    Zhu, W.2
  • 23
    • 58049210564 scopus 로고    scopus 로고
    • Modern methods for asymmetric hydrogenation of ketones
    • Marques, MMB (2006) Modern methods for asymmetric hydrogenation of ketones. Org Chem Highlights.
    • (2006) Org Chem Highlights
    • Marques, M.M.B.1
  • 24
    • 0036898467 scopus 로고    scopus 로고
    • 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
    • Marukawa, K. and Mori, K. (2002) 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, 23, pp. 3974-3978.
    • (2002) Eur J Org Chem , vol.23 , pp. 3974-3978
    • Marukawa, K.1    Mori, K.2
  • 25
    • 0037291745 scopus 로고    scopus 로고
    • Thalidomide: A review of approved and investigational uses
    • Matthews, SJ and McCoy, C. (2003) Thalidomide: A review of approved and investigational uses. Clin Ther, 25, pp. 342-395.
    • (2003) Clin Ther , vol.25 , pp. 342-395
    • Matthews, S.J.1    McCoy, C.2
  • 26
    • 4544247135 scopus 로고    scopus 로고
    • Indium (III) acetate-catalyzed 1,4-reduction and reductive aldol reactions of (-enones with phenylsilane
    • Miura, K., Yamada, Y., Tomita, M. and Hosomi, A. (2004) Indium (III) acetate-catalyzed 1,4-reduction and reductive aldol reactions of (-enones with phenylsilane. Synlett, 11, pp. 1985-1989.
    • (2004) Synlett , vol.11 , pp. 1985-1989
    • Miura, K.1    Yamada, Y.2    Tomita, M.3    Hosomi, A.4
  • 28
    • 0347474982 scopus 로고    scopus 로고
    • Recent developments in asymmetric reduction of ketones with biocatalysts
    • Nakamura, K., Yamanaka, R., Matsuda, T. and Harada, T. (2003) Recent developments in asymmetric reduction of ketones with biocatalysts. Tetrahedron: Asymmetry, 14, pp. 2659-2681.
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 2659-2681
    • Nakamura, K.1    Yamanaka, R.2    Matsuda, T.3    Harada, T.4
  • 30
    • 39049190841 scopus 로고    scopus 로고
    • Influence of water-miscible organic solvents on kinetics and enantioselectivity of the (R)-specific alcohol dehydrogenase from Lactobacillus brevis
    • Schumacher, J., Eckstein, M. and Kragl, U. (2006) Influence of water-miscible organic solvents on kinetics and enantioselectivity of the (R)-specific alcohol dehydrogenase from Lactobacillus brevis. Biotechnol J, 1, pp. 574-581.
    • (2006) Biotechnol J , vol.1 , pp. 574-581
    • Schumacher, J.1    Eckstein, M.2    Kragl, U.3
  • 31
  • 32
    • 31944432298 scopus 로고    scopus 로고
    • Diastereoselective reduction of (-keto carbonyl compounds by cultured plant cells
    • Shimoda, K., Kubota, N., Hamada, H. and Hamada, H. (2006) Diastereoselective reduction of (-keto carbonyl compounds by cultured plant cells. Tetrahedron Lett, 47, pp. 1541-1544.
    • (2006) Tetrahedron Lett , vol.47 , pp. 1541-1544
    • Shimoda, K.1    Kubota, N.2    Hamada, H.3    Hamada, H.4
  • 33
    • 0034728936 scopus 로고    scopus 로고
    • Synthesis of carbocycles by enone-selective reduction using organoiodotin hydride
    • Suwa, T., Nishino, K., Miyatake, M., Shibata, I. and Baba, A. (2000) Synthesis of carbocycles by enone-selective reduction using organoiodotin hydride. Tetrahedron Lett, 41, pp. 3403-3406.
    • (2000) Tetrahedron Lett , vol.41 , pp. 3403-3406
    • Suwa, T.1    Nishino, K.2    Miyatake, M.3    Shibata, I.4    Baba, A.5
  • 34
    • 0031968226 scopus 로고    scopus 로고
    • Bioconversion of optically active pyridil alcohols from the corresponding racemates with plant cell cultures
    • Takemoto, M. and Achiwa, K. (1998) Bioconversion of optically active pyridil alcohols from the corresponding racemates with plant cell cultures. Chem Pharm Bull, 46, pp. 577-580.
    • (1998) Chem Pharm Bull , vol.46 , pp. 577-580
    • Takemoto, M.1    Achiwa, K.2
  • 35
    • 0031742234 scopus 로고    scopus 로고
    • Deracemization of racemic 4-pyridyl-1-ethanol by Catharanthus roseus cell cultures
    • Takemoto, M. and Achiwa, K. (1998) Deracemization of racemic 4-pyridyl-1-ethanol by Catharanthus roseus cell cultures. Phytochemistry, 49, pp. 1627-1629.
    • (1998) Phytochemistry , vol.49 , pp. 1627-1629
    • Takemoto, M.1    Achiwa, K.2
  • 36
    • 0032703858 scopus 로고    scopus 로고
    • Quantitative determination of thalidomide in human serum with high-performance liquid chromatography using protein precipitation with trichloroacetic acid and ultraviolet detection
    • Torano, JS, Verbon, A. and Guchelaar, H-J. (1999) Quantitative determination of thalidomide in human serum with high-performance liquid chromatography using protein precipitation with trichloroacetic acid and ultraviolet detection. J Chromatogr B, 734, pp. 203-210.
    • (1999) J Chromatogr B , vol.734 , pp. 203-210
    • Torano, J.S.1    Verbon, A.2    Guchelaar, H.-J.3
  • 37
    • 17844390995 scopus 로고    scopus 로고
    • Configurational stability of 2-benzoylcyclohexanone: Unexpected solvent effects on the rate of racemization
    • Tumambac, GE, Francis, CJ and Wolf, C. (2005) Configurational stability of 2-benzoylcyclohexanone: Unexpected solvent effects on the rate of racemization. Chirality, 17, pp. 171-176.
    • (2005) Chirality , vol.17 , pp. 171-176
    • Tumambac, G.E.1    Francis, C.J.2    Wolf, C.3
  • 38
    • 0037077589 scopus 로고    scopus 로고
    • 2-silane (dpm=2,2,6,6-tetramethylheptane-3,5-dionate): Mechanism and partitioning of hydrometallative versus anion radical pathways
    • 2-silane (dpm= 2,2,6,6-tetramethylheptane-3,5-dionate): Mechanism and partitioning of hydrometallative versus anion radical pathways. J Am Chem Soc, 124, pp. 9448-9453.
    • (2002) J Am Chem Soc , vol.124 , pp. 9448-9453
    • Wang, L.-C.1    Jang, H.-Y.2    Roh, Y.3    Lynch, V.4    Schultz, A.J.5    Wang, X.6    Krische, M.J.7
  • 39
    • 23944454575 scopus 로고    scopus 로고
    • Biotransformation of α-santonin by cell suspension cultures of five plants
    • Yang, L., Dai, J., Sakai, J. and Ando, M. (2005) Biotransformation of α-santonin by cell suspension cultures of five plants. Biotechnol Lett, 27, pp. 793-797.
    • (2005) Biotechnol Lett , vol.27 , pp. 793-797
    • Yang, L.1    Dai, J.2    Sakai, J.3    Ando, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.