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2442770911
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Sept. 28
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(a) The enantiopure drug market has been estimated as US $18 billion worldwide. See: Stinson, S. C. Chem. Eng. News 1992, Sept. 28, 46-78;
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Chem. Eng. News
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Stinson, S.C.1
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25344475431
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Wiley: Chichester
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(c) Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds, Chirality in Industry, Wiley: Chichester, Vol. I, 1992; Vol. II, 1997.
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Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826.
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Schoffers, E.1
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(a) Horeau, A. Tetrahedron 1975, 31, 1307-1309;
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Horeau, A.1
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7
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20644469267
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(b) for biocatalyzed reactions: Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294-7299;
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Sih, C.J.4
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8
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33845557915
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(c) for non-biocatalyzed reactions: Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237-6240;
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Martin, V.S.1
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Ikeda, M.5
Sharpless, K.B.6
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9
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8044227965
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(d) for prebiotic reactions: Balavoine, G.; Moradpour, A.; Kagan, H. B. J. Am. Chem. Soc. 1974, 96, 5152-5158.
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Balavoine, G.1
Moradpour, A.2
Kagan, H.B.3
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10
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0344280618
-
-
In biocatalyzed reactions, the ratio of asymmetrizations versus kinetic resolutions is ∼1:4, database Faber, ∼9000 entries
-
In biocatalyzed reactions, the ratio of asymmetrizations versus kinetic resolutions is ∼1:4, database Faber, ∼9000 entries.
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12
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0030737815
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Ebbers, E. J.; Ariaans, G. J. A.; Houbiers, J. P. M.; Bruggink, A.; Zwanenburg, B. Tetrahedron 1997, 53, 9417-9476.
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Ebbers, E.J.1
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Zwanenburg, B.5
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0002923489
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Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn 1995, 68, 36-56.
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Noyori, R.1
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84907036080
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Buisson, D.; Azerad, R.; Sanner, C.; Larcheveque, M. Biocatalysis 1992, 5, 249-265.
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Buisson, D.1
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17
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0029153701
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Nakamura, K.; Inoue, Y.; Matsuda, T.; Ohno, A. Tetrahedron Lett. 1995, 36, 6263-6266.
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Nakamura, K.1
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0029618386
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Fantin, G.; Fogagnolo, M.; Giovannini, P. P.; Medici, A.; Pedrini, P. Tetrahedron: Asymmetry 1995, 6, 3047-3053.
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Fantin, G.1
Fogagnolo, M.2
Giovannini, P.P.3
Medici, A.4
Pedrini, P.5
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0027050187
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Tsuchiya, S.; Miyamoto, K.; Ohta, H. Biotechnol. Lett. 1992, 14, 1137-1142.
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Tsuchiya, S.1
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0028970755
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Takahashi, E.; Nakamichi, K.; Furui, M. J. Ferment. Bioeng. 1995, 80, 247-250.
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Takahashi, E.1
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0028156837
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Carnell, A. J.; Iacazio, G.; Roberts, S. M.; Willette, A. J. Tetrahedron Lett. 1994, 35, 331-334.
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Carnell, A.J.1
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0028247067
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Matsumura, S.; Kawai, Y.; Takahashi, Y.; Toshima, K. Biotechnol. Lett. 1994, 16, 485-490.
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Biotechnol. Lett.
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Matsumura, S.1
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0023381801
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Shimizu, S.; Hattori, S.; Hata, H.; Yamada, H. Enzyme Microb. Technol. 1987, 9, 411-416.
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Shimizu, S.1
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Yamada, H.4
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25
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84949070047
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+-linked dehydrogenase and an (S)-specific NADPH-dependent reductase: Hasegawa, J.; Ogura, M.; Tsuda, S.; Maemoto, S.; Kutsuki, H.; Ohashi, T. Agric. Biol. Chem. 1990, 54, 1819-1827. On the other hand, observations on the fungus Geotrichum candidum prove the need for molecular oxygen, which would suggest the involvement of an alcohol oxidase rather than an alcohol dehydrogenase: Azerad, R.; Buisson, D. Stereocontrolled reduction of β-ketoesters with Geotrichum candidum. Servi, S., Ed. In Microbial Reagents in Organic Synthesis, Vol. 381, NATO ASI Series C, Kluwer: Dordrecht, 1992; pp. 421-440.
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Hasegawa, J.1
Ogura, M.2
Tsuda, S.3
Maemoto, S.4
Kutsuki, H.5
Ohashi, T.6
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26
-
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0005530024
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Stereocontrolled reduction of β-ketoesters with Geotrichum candidum
-
Servi, S., Ed. NATO ASI Series C, Kluwer: Dordrecht
-
+-linked dehydrogenase and an (S)-specific NADPH-dependent reductase: Hasegawa, J.; Ogura, M.; Tsuda, S.; Maemoto, S.; Kutsuki, H.; Ohashi, T. Agric. Biol. Chem. 1990, 54, 1819-1827. On the other hand, observations on the fungus Geotrichum candidum prove the need for molecular oxygen, which would suggest the involvement of an alcohol oxidase rather than an alcohol dehydrogenase: Azerad, R.; Buisson, D. Stereocontrolled reduction of β-ketoesters with Geotrichum candidum. Servi, S., Ed. In Microbial Reagents in Organic Synthesis, Vol. 381, NATO ASI Series C, Kluwer: Dordrecht, 1992; pp. 421-440.
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(1992)
Microbial Reagents in Organic Synthesis
, vol.381
, pp. 421-440
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Azerad, R.1
Buisson, D.2
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27
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0345142992
-
-
E.e.=93.75% after four cycles; however, for an e.e. of 100%, an infinite number of cycles is required in theory
-
E.e.=93.75% after four cycles; however, for an e.e. of 100%, an infinite number of cycles is required in theory.
-
-
-
-
28
-
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0001322821
-
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For the mathematical treatment of dynamic kinetic resolutions see: Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144-152; Kitamura, M.; Tokunaga, M.; Noyori, R. Tetrahedron 1993, 49, 1853-1860.
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(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 144-152
-
-
Kitamura, M.1
Tokunaga, M.2
Noyori, R.3
-
29
-
-
0027400239
-
-
For the mathematical treatment of dynamic kinetic resolutions see: Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144-152; Kitamura, M.; Tokunaga, M.; Noyori, R. Tetrahedron 1993, 49, 1853-1860.
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(1993)
Tetrahedron
, vol.49
, pp. 1853-1860
-
-
Kitamura, M.1
Tokunaga, M.2
Noyori, R.3
-
30
-
-
0345574556
-
-
This can be conveniently explained by different paths of various gradient leading to a hilltop, the gradient determines the length of each path to reach the top
-
This can be conveniently explained by different paths of various gradient leading to a hilltop, the gradient determines the length of each path to reach the top.
-
-
-
-
31
-
-
0345142991
-
-
The term 'theoretical turnover' indicates the theoretical equivalents of reagents needed if oxidation and reduction are considered as 'ideal' reactions. In practice, however, the amounts required will be larger because excess reagent(s) may be needed in order to drive the reaction towards completion and/or due to decomposition of reagents during undesired side reactions
-
The term 'theoretical turnover' indicates the theoretical equivalents of reagents needed if oxidation and reduction are considered as 'ideal' reactions. In practice, however, the amounts required will be larger because excess reagent(s) may be needed in order to drive the reaction towards completion and/or due to decomposition of reagents during undesired side reactions.
-
-
-
-
32
-
-
0344712555
-
-
Alternatively, the Poe-scale can be used. The Poe-value corresponding to a time-value can be easily calculated through the e.e. at a given point of the reaction
-
Alternatively, the Poe-scale can be used. The Poe-value corresponding to a time-value can be easily calculated through the e.e. at a given point of the reaction.
-
-
-
-
33
-
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0344280613
-
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Kroutil, W.; Faber, K. (© 1998). 'Cyclo' is a free shareware program run through Windows. The program is available via the Internet at http://www-orgc.tu-graz.ac.at or directly from the authors. A description of how to use the program is given in the help-file which accompanies the program.
-
(1998)
-
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Kroutil, W.1
Faber, K.2
-
34
-
-
0344280612
-
-
No maximum for P is observed if the amount of reducing agent is below the theoretical turnover. In this case, the process is disrupted by termination of the reverse reaction through lack of reducing agent
-
No maximum for P is observed if the amount of reducing agent is below the theoretical turnover. In this case, the process is disrupted by termination of the reverse reaction through lack of reducing agent.
-
-
-
-
35
-
-
0344712554
-
-
In order to reduce the Tht down to the absolute minimum (Tht=1), absolute selectivity (E=∞) is required
-
In order to reduce the Tht down to the absolute minimum (Tht=1), absolute selectivity (E=∞) is required.
-
-
-
-
36
-
-
0345574555
-
-
2 carbon atoms), the process is linked to oxidation and reduction
-
2 carbon atoms), the process is linked to oxidation and reduction.
-
-
-
-
37
-
-
0344712553
-
-
note
-
In principle, redox-systems comprising three types of chiral centers may be envisaged: (i) sec-alcohol/ketone [EC 1.1.3.X], (ii) sec-amine/imine [EC 1.4.3.X] and (iii) alkane/alkene [EC 1.3.3.X]. For the latter system, however, no feasible enantioselective biocatalytic oxidation system has been described to date.
-
-
-
-
38
-
-
0345142990
-
-
note
-
2+ or non-heme iron are involved.
-
-
-
-
39
-
-
0025865149
-
-
For the enantioselective oxidation of sec-alcohols by sec-alcohol oxidases see: Müller, H.-G.; Güntherberg, H.; Drechsler, H.; Mauersberger, S.; Kortus, K.; Oehme, G. Tetrahedron Lett. 1991, 32, 2009-2012; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P.; Poli, S.; Gardini, F. Tetrahedron: Asymmetry 1993, 4, 1607-1612.
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Tetrahedron Lett.
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-
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Müller, H.-G.1
Güntherberg, H.2
Drechsler, H.3
Mauersberger, S.4
Kortus, K.5
Oehme, G.6
-
40
-
-
0027274941
-
-
For the enantioselective oxidation of sec-alcohols by sec-alcohol oxidases see: Müller, H.-G.; Güntherberg, H.; Drechsler, H.; Mauersberger, S.; Kortus, K.; Oehme, G. Tetrahedron Lett. 1991, 32, 2009-2012; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P.; Poli, S.; Gardini, F. Tetrahedron: Asymmetry 1993, 4, 1607-1612.
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(1993)
Tetrahedron: Asymmetry
, vol.4
, pp. 1607-1612
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Fantin, G.1
Fogagnolo, M.2
Medici, A.3
Pedrini, P.4
Poli, S.5
Gardini, F.6
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41
-
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0028903071
-
-
For the enantioselective oxidation of sec-alcohols by cholesterol oxidase see: Dieth, S.; Tritsch, D.; Biellmann, J.-F. Tetrahedron Lett. 1995, 36, 2243-2246.
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(1995)
Tetrahedron Lett.
, vol.36
, pp. 2243-2246
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Dieth, S.1
Tritsch, D.2
Biellmann, J.-F.3
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43
-
-
0030859143
-
-
For the enantioselective oxidation of α-hydroxyacids by glycolate oxidase see: Gavagan, J. E.; Fager, S. K.; Seip, J. E.; Clark, D. S.; Payne, M. S.; Anton, D. L.; DiCosimo, R. J. Org. Chem. 1997, 62, 5419-5427; Eisenberg, A.; Seip, J. E.; Gavagan, J. E.; Payne, M. S.; Anton, D. L.; DiCosimo, R. J. Mol. Catal. B 1997, 2, 223-232; Adam, W.; Lazarus, M.; Boss, B.; Saha-Möller, C. R.; Humpf, H.-U.; Schreier, P. J. Org. Chem. 1997, 62, 7841-7843.
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Gavagan, J.E.1
Fager, S.K.2
Seip, J.E.3
Clark, D.S.4
Payne, M.S.5
Anton, D.L.6
Dicosimo, R.7
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44
-
-
0031073093
-
-
For the enantioselective oxidation of α-hydroxyacids by glycolate oxidase see: Gavagan, J. E.; Fager, S. K.; Seip, J. E.; Clark, D. S.; Payne, M. S.; Anton, D. L.; DiCosimo, R. J. Org. Chem. 1997, 62, 5419-5427; Eisenberg, A.; Seip, J. E.; Gavagan, J. E.; Payne, M. S.; Anton, D. L.; DiCosimo, R. J. Mol. Catal. B 1997, 2, 223-232; Adam, W.; Lazarus, M.; Boss, B.; Saha-Möller, C. R.; Humpf, H.-U.; Schreier, P. J. Org. Chem. 1997, 62, 7841-7843.
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Eisenberg, A.1
Seip, J.E.2
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Payne, M.S.4
Anton, D.L.5
Dicosimo, R.6
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45
-
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0000538529
-
-
For the enantioselective oxidation of α-hydroxyacids by glycolate oxidase see: Gavagan, J. E.; Fager, S. K.; Seip, J. E.; Clark, D. S.; Payne, M. S.; Anton, D. L.; DiCosimo, R. J. Org. Chem. 1997, 62, 5419-5427; Eisenberg, A.; Seip, J. E.; Gavagan, J. E.; Payne, M. S.; Anton, D. L.; DiCosimo, R. J. Mol. Catal. B 1997, 2, 223-232; Adam, W.; Lazarus, M.; Boss, B.; Saha-Möller, C. R.; Humpf, H.-U.; Schreier, P. J. Org. Chem. 1997, 62, 7841-7843.
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Adam, W.1
Lazarus, M.2
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Humpf, H.-U.5
Schreier, P.6
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0031420391
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Hartmann, C.; McIntire, W. S. Methods Enzymol. 1997, 250, 98-150; Frebort, I.; Adachi, O. J. Ferment. Bioeng. 1995, 80, 625-632.
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Hartmann, C.1
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Hartmann, C.; McIntire, W. S. Methods Enzymol. 1997, 250, 98-150; Frebort, I.; Adachi, O. J. Ferment. Bioeng. 1995, 80, 625-632.
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Frebort, I.1
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77956995393
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From the large number of amino acid oxidases, those showing wide substrate tolerance are of particular interest, see: Rodwell, V. W. Methods Enzymol. 1971, 17B, 174-188; Wikström, P.; Szwajcer, E.; Brodelius, P.; Nilsson, K.; Mosbach, K. Biotechnol. Lett. 1982, 4, 153-158.
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Rodwell, V.W.1
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50
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0020057182
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From the large number of amino acid oxidases, those showing wide substrate tolerance are of particular interest, see: Rodwell, V. W. Methods Enzymol. 1971, 17B, 174-188; Wikström, P.; Szwajcer, E.; Brodelius, P.; Nilsson, K.; Mosbach, K. Biotechnol. Lett. 1982, 4, 153-158.
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