PMID- 28727894
OWN - NLM
STAT- MEDLINE
DCOM- 20190403
LR  - 20210109
IS  - 1521-3773 (Electronic)
IS  - 1433-7851 (Print)
IS  - 1433-7851 (Linking)
VI  - 56
IP  - 41
DP  - 2017 Oct 2
TI  - Enzymatic and Chemoenzymatic Three-Step Cascades for the Synthesis of 
      Stereochemically Complementary Trisubstituted Tetrahydroisoquinolines.
PG  - 12503-12507
LID - 10.1002/anie.201705855 [doi]
AB  - Chemoenzymatic and enzymatic cascade reactions enable the synthesis of complex 
      stereocomplementary 1,3,4-trisubstituted tetrahydroisoquinolines (THIQs) with 
      three chiral centers in a step-efficient and selective manner without 
      intermediate purification. The cascade employs inexpensive substrates 
      (3-hydroxybenzaldehyde and pyruvate), and involves a carboligation step, a 
      subsequent transamination, and finally a Pictet-Spengler reaction with a carbonyl 
      cosubstrate. Appropriate selection of the carboligase and transaminase enzymes 
      enabled the biocatalytic formation of (1R,2S)-metaraminol. Subsequent cyclization 
      catalyzed either enzymatically by a norcoclaurine synthase or chemically by 
      phosphate resulted in opposite stereoselectivities in the products at the C1 
      position, thus providing access to both orientations of the THIQ C1 substituent. 
      This highlights the importance of selecting from both chemo- and biocatalysts for 
      optimal results.
CI  - (c) 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
FAU - Erdmann, Vanessa
AU  - Erdmann V
AD  - IBG-1: Biotechnology, Forschungszentrum Julich GmbH, 52425, Julich, Germany.
FAU - Lichman, Benjamin R
AU  - Lichman BR
AD  - John Innes Centre, Norwich Research Park, Norwich, NR4 7UH, UK.
FAU - Zhao, Jianxiong
AU  - Zhao J
AD  - Department of Chemistry, University College London, London, WC1H 0AJ, UK.
FAU - Simon, Robert C
AU  - Simon RC
AD  - Roche-Diagnostics GmbH, DOZCBE, 82377, Penzberg, Germany.
FAU - Kroutil, Wolfgang
AU  - Kroutil W
AD  - Department of Chemistry, University of Graz, 8010, Graz, Austria.
FAU - Ward, John M
AU  - Ward JM
AD  - Department of Biochemical Engineering, University College London, London, WC1E 
      6BT, UK.
FAU - Hailes, Helen C
AU  - Hailes HC
AD  - Department of Chemistry, University College London, London, WC1H 0AJ, UK.
FAU - Rother, Dorte
AU  - Rother D
AUID- ORCID: 0000-0002-2339-4431
AD  - IBG-1: Biotechnology, Forschungszentrum Julich GmbH, 52425, Julich, Germany.
LA  - eng
GR  - Wellcome Trust/United Kingdom
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20170906
PL  - Germany
TA  - Angew Chem Int Ed Engl
JT  - Angewandte Chemie (International ed. in English)
JID - 0370543
RN  - 0 (Tetrahydroisoquinolines)
RN  - EC 2.2.1.6 (Acetolactate Synthase)
RN  - EC 2.6.1.- (Transaminases)
RN  - EC 6.3.- (Carbon-Nitrogen Ligases)
RN  - EC 6.3.3.- (norcoclaurine synthase)
SB  - IM
MH  - Acetolactate Synthase/chemistry
MH  - Biocatalysis
MH  - Carbon-Nitrogen Ligases/chemistry
MH  - Catalysis
MH  - Chemistry Techniques, Synthetic
MH  - Chromobacterium/enzymology
MH  - Escherichia coli/enzymology
MH  - Stereoisomerism
MH  - Tetrahydroisoquinolines/*chemical synthesis/chemistry
MH  - Thalictrum/enzymology
MH  - Transaminases/chemistry
PMC - PMC5658969
OTO - NOTNLM
OT  - asymmetric catalysis
OT  - biocatalysis
OT  - chemoenzymatic cascades
OT  - norcoclaurine synthase
OT  - transaminases
COIS- The authors declare no conflict of interest.
EDAT- 2017/07/21 06:00
MHDA- 2019/04/04 06:00
PMCR- 2017/10/27
CRDT- 2017/07/21 06:00
PHST- 2017/06/08 00:00 [received]
PHST- 2017/07/21 06:00 [pubmed]
PHST- 2019/04/04 06:00 [medline]
PHST- 2017/07/21 06:00 [entrez]
PHST- 2017/10/27 00:00 [pmc-release]
AID - ANIE201705855 [pii]
AID - 10.1002/anie.201705855 [doi]
PST - ppublish
SO  - Angew Chem Int Ed Engl. 2017 Oct 2;56(41):12503-12507. doi: 
      10.1002/anie.201705855. Epub 2017 Sep 6.