Process design implications of aldehyde properties on transketolase-catalysed condensations

Recently we have devised a systematic approach to selection and operation of biotransforma-tion reactions. Such an approach is based on reaction characterisation leading to the identification of constraints and subsequent process synthesis. In this paper we illustrate how this approach can be applied to a model system (condensation of glycolaldehyde with β-hydroxy-pyruvate by transketolase to synthesise L-erythrulose) as the basis for rapidly evaluating a second system with different aldehyde properties (condensation of racemic 3-oxy-benzylglycer-aldehyde with β-hydroxypyruvate to synthesise (3S,4R)-5-oxy-benzyl-D-xylulose). Some general conclusions are drawn.

[1]  John M. Woodley,et al.  Carbon‐Carbon Bond Synthesis , 1996 .

[2]  J. Woodley,et al.  A useful assay for transketolase in asymmetric syntheses , 1996 .

[3]  John M. Woodley,et al.  Biotransformation reactor selection and operation , 1994 .

[4]  J. Villafranca,et al.  Heptulose synthesis from nonphosphorylated aldoses and ketoses by spinach transketolase. , 1971, The Journal of biological chemistry.

[5]  R. Kluger,et al.  Thiamin diphosphate: a mechanistic update on enzymic and nonenzymic catalysis of decarboxylation , 1987 .

[6]  John M. Woodley,et al.  Escherichia coli transketolase-catalyzed carbon-carbon bond formation: biotransformation characterization for reactor evaluation and selection , 1998 .

[7]  Michael Gyamerah,et al.  Kinetics of overexpressed transketolase from Escherichia coli JM 107/pQR 700 , 1997 .

[8]  E. Racker,et al.  Thiamine pyrophosphate, a coenzyme of transketolase , 1953 .

[9]  M. Lilly,et al.  Enzyme-catalysed carbon-carbon bond formation: large-scale production of Escherichia coli transketolase. , 1996, Journal of biotechnology.

[10]  H. Kayakiri,et al.  Structure of FR 900483, a new immunomodulator isolated from a fungus , 1988 .

[11]  C. Demuynck,et al.  Study of the specificity of a spinach transketolase on achiral substrates , 1993 .

[12]  J. Cooper,et al.  The oxidative pentose phosphate cycle. I. Preparation of substrates and enzymes. , 1958, Archives of biochemistry and biophysics.

[13]  T. Ziegler,et al.  Preparation of optically pure L-2-hydroxyaldehydes with yeast transketolase , 1992 .