2.1. 5 Addition to C=N Bonds
Book
Editors: Faber, K.; Fessner, W.-D.; Turner, N. J.
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
Science of Synthesis Reference Libraries
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Type: Multivolume Edition
Abstract
![](https://www.thieme-connect.de/media/10.1055-b-003-125813/thumbnails/a_210cce.jpg)
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- 8 Geu-Flores F, Sherden NH, Courdavault V, Burlat V, Glenn WS, Wu C, Nims E, Cui Y, OʼConnor SE. Nature (London) 2012; 492: 138
- 11 Maresh JJ, Giddings L.-A, Friedrich A, Loris EA, Panjikar S, Trout BL, Stöckigt J, Peters B, OʼConnor SE. J. Am. Chem. Soc. 2008; 130: 710
- 12 Ilari A, Franceschini S, Bonamore A, Arenghi F, Botta B, Macone A, Pasquo A, Bellucci L, Boffi A. J. Biol. Chem. 2009; 284: 897
- 14 Itoh A, Tanahashi T, Tabata M, Shikata M, Kakite M, Nagai M, Nagakura N. Phytochemistry 2001; 56: 623
- 20 Crowe S MS Thesis, DePaul University 2013 http://via.library.depaul.edu/csh_etd/55/ (accessed May 2014
- 22 Bonamore A, Rovardi I, Gasparrini F, Baiocco P, Barba M, Molinaro C, Botta B, Boffi A, Macone A. Green Chem. 2010; 12: 1623
- 28 Loris EA, Panjikar S, Ruppert M, Barleben L, Unger M, Schübel H, Stöckigt J. Chem. Biol. (Oxford, U. K.) 2007; 14: 979
- 31 Wu F, Zhu H, Sun L, Rajendran C, Wang M, Ren X, Panjikar S, Cherkasov A, Zou H, Stöckigt J. J. Am. Chem. Soc. 2012; 134: 1498
- 32 Matter H, Scheiper B, Steinhagen H, Böcskei Z, Fleury V, McCort G. Bioorg. Med. Chem. Lett. 2011; 21: 5487