Can the combination of electrochemical regeneration of NAD+, selectivity of L‐α‐amino‐acid dehydrogenase, and reductive amination of α‐keto‐acid be applied to the inversion of configuration of a L‐α‐amino‐acid?

作者: Agn�s Anne , Christian Bourdillon , Sandra Daninos , Jacques Moiroux

DOI: 10.1002/(SICI)1097-0290(19990705)64:1<101::AID-BIT11>3.0.CO;2-L

关键词: DehydrogenaseCombinatorial chemistryCofactorElectrochemical regenerationAmmoniaImineChemical reactionReductive aminationNAD+ kinaseOrganic chemistryChemistry

摘要: The inversion of configuration L-alanine can be carried out by combining its selective oxidation in the presence NAD+ and dehydrogenase, electrochemical regeneration at a carbon felt anode, reductive amination pyruvate, i.e., reduction imino derivative mercury cathode, reaction mixture being buffered with concentrated ammonium/ammonia (1.28M / 1.28M). dehydrogenase exhibits astonishing activity stability under such extreme conditions pH ionic strength. The main drawback process is slowness. At best, complete 10 mM solution requires 140 h. A careful detailed quantitative analysis each key steps involved shows that enzyme catalyzed so thermodynamically uphill it driven efficiently to completion only when both coenzyme pyruvate are very effective. first condition easily fulfilled. Under best conditions, rate chemical producing imine which controls whole kinetically. © 1999 John Wiley & Sons, Inc. Biotechnol Bioeng 64: 101–107, 1999.

参考文章(23)
Ronald L. Blankespoor, Larry L. Miller, Electrochemical oxidation of NADH Journal of Electroanalytical Chemistry and Interfacial Electrochemistry. ,vol. 171, pp. 231- 241 ,(1984) , 10.1016/0022-0728(84)80116-3
Jacques Bonnefoy, Jacques Moiroux, Jean-Marc Laval, Christian Bourdillon, Electrochemical regeneration of NAD+. A new evaluation of its actual yield Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases. ,vol. 84, pp. 941- 950 ,(1988) , 10.1039/F19888400941
Jean-Marc Laval, Christian Bourdillon, Jacques Moiroux, The electrochemical regeneration of NAD(+) revisited. Biotechnology and Bioengineering. ,vol. 30, pp. 157- 159 ,(1987) , 10.1002/BIT.260300203
Björn Persson, Lo Gorton, Gillis Johansson, Arne Torstensson, Biofuel anode based on d-glucose dehydrogenase, nicotinamide adenine dinucleotide and a modified electrode Enzyme and Microbial Technology. ,vol. 7, pp. 549- 552 ,(1985) , 10.1016/0141-0229(85)90097-3
Allen J. Bard, Emanuel Solon, SECONDARY REACTIONS IN CONTROLLED POTENTIAL COULOMETRY. III. PRECEDING AND SIMULTANEOUS CHEMICAL REACTIONS The Journal of Physical Chemistry. ,vol. 67, pp. 2326- 2330 ,(1963) , 10.1021/J100805A016
Wim A.C. Somers, Wim van Hartingsveldt, Edwin C.A. Stigter, Jan Pieter van der Lugt, Electrochemical regeneration of redox enzymes for continuous use in preparative processes Trends in Biotechnology. ,vol. 15, pp. 495- 500 ,(1997) , 10.1016/S0167-7799(97)89424-3
Bineta Keita, Khalid Essaadi, Louis Nadjo, Michel Desmadril, Rate-limiting one-electron transfer in the oxidation of NADH by polyoxometalates Chemical Physics Letters. ,vol. 237, pp. 411- 418 ,(1995) , 10.1016/0009-2614(95)00331-W