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Faber, K. et al.: 2015 Science of Synthesis: Biocatalysis Organic Synthesis 2 DOI: 10.1055/sos-SD-215-00081
Biocatalysis in Organic Synthesis 2

2.1.5 Addition to C=N Bonds

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Book

Editors: Faber, K.; Fessner, W.-D.; Turner, N. J.

Authors: Au, S. K.; Bartsch, S.; Beecher, D.; Boffi, A.; Bommarius, A. S.; Bonamore, A.; Brown, G.; Busto, E.; Clapés, P.; Faber, K.; Fischereder, E.-M.; France, S. P.; Fuchs, C. S.; Geertsema, E. M.; Glieder, A.; Gruber-Khadjawi, M.; Hall, M.; Hanefeld, U.; Hussain, S.; Ilari, A.; Janssen, D. B.; Kaluđerović, G. N.; Kroutil, W.; Lamm, A. S.; Leipold, F.; Lewin, R.; Li, A. T.; Li, Z.; Majerić Elenkov, M.; Micklefield, J.; Moody, T. S.; Mix, S.; Müller, M.; Poelarends, G. J.; Pohl, M.; Pressnitz, D.; Resch, V.; Richter, N.; Rosazza, J. P. N.; Schreckenbach, H. F.; Simon, R. C.; Steiner, K.; Szymański, W.; Thompson, M. L.; Turner, N. J.; Venkitasubramanian, P.; Vogel, A.; Wechsler, C.; Wessjohann, L. A.; Wohlgemuth, R.

Title: Biocatalysis Organic Synthesis 2

Print ISBN: 9783131741615; Online ISBN: 9783131975317; Book DOI: 10.1055/b-003-125813

1st edition © 2015. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

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Abstract

The Pictet–Spengler reaction consists of a Mannich-type cyclization in which an electron-rich aromatic carbon attacks a C=N bond, in the form of an electrophilic iminium ion, thus yielding a heterocyclic scaffold and generating a new asymmetric center. In this chapter, the substrate scope and limitations of the best-known Pictet–Spenglerase enzymes are discussed in order to pave the way for development of a general biocatalytic strategy for the stereoselective addition to the C=N bond.

Key words

Pictet–Spengler reaction - tetrahydroisoquinolines - indole alkaloids - strictosidine synthase - norcoclaurine synthase - β-carbolines - azaindoles
 
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