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Biotransformations in Organic Chemistry pp 315–405Cite as

Special Techniques

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Abstract

Most biocatalysts can be used in a straightforward manner by regarding them as chiral catalysts and by applying standard methodology, i.e., in buffered aqueous solution. In order to broaden the applicability of enzymes, some special techniques have been developed. In particular, using biocatalysts in nonaqueous media rather than in water can lead to the gain of some significant advantages as long as some specific guidelines are followed [1]. Furthermore, ‘fixation’ of the enzyme by immobilization may be necessary, and the use of membrane technology may be advantageous as well. For both of the latter topics only the most simple techniques which can be adopted in an average organic chemistry laboratory are discussed (Sect. 3.3).

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Notes

  1. 1.

    Tcrit 31 °C and pcrit 73 bar.

  2. 2.

    In principle, ethyl fluoroacetate would also fall into this category. However, its use is not recommended since fluoroacetic acid is a severe toxin by acting as inhibitor of the Krebs-cycle.

  3. 3.

    Sometimes, this proceeds via thioester intermediates.

  4. 4.

    Metallo- or carboxy-proteases, which do not form a covalent acyl enzyme intermediate are usually unsuitable.

  5. 5.

    Domino-reactions are also called ‘zipper-reactions’.

  6. 6.

    With the rare exception of proteases.

  7. 7.

    The enzyme from rabbit muscle (RAMA) is commonly used to catalyse the reverse aldol reaction (Sect. 2.4.1).

  8. 8.

    Hydrogen-transfer reactions are known since 1925: Meerwein H, Schmidt H (1925) Liebigs Ann. Chem. 444: 221; Verley A (1925) Bull. Soc. Fr. 37: 537.

  9. 9.

    DEAE cellulose and sephadex are popular stationary phases for protein chromatography.

  10. 10.

    A popular membrane from daily life is Gore-Tex™.

  11. 11.

    For instance, glutamic acid dioleyl ester ribitol amide, didodecyl N-d-glucono-l-glutamate or Brij35.

  12. 12.

    Also denoted as vitamin H.

  13. 13.

    The transition state is related to the binding cavity like the ‘negative’ to a photographic picture.

  14. 14.

    Today, approximately 100,000 structure files are available from the Protein Data Bank and about a dozen are added every day.

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    Kurt Faber

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Faber, K. (2018). Special Techniques. In: Biotransformations in Organic Chemistry. Springer, Cham. https://doi.org/10.1007/978-3-319-61590-5_3

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