Literature DB >> 22966211

Biocatalytic production of tetrahydroisoquinolines.

Bettina M Ruff1, S Bräse, Sarah E O'Connor.   

Abstract

The promiscuity of the enzyme norcoclaurine synthase is described. This biocatalyst yielded a diverse array of substituted tetrahydroisoquinolines by cyclizing dopamine with various acetaldehydes in a Pictet-Spengler reaction. This enzymatic reaction may provide a biocatalytic route to a range of tetrahydroisoquinoline alkaloids.

Entities:  

Year:  2012        PMID： 22966211      PMCID： PMC3435518          DOI： 10.1016/j.tetlet.2011.12.089

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.032


  22 in total

1.  Phosphate mediated biomimetic synthesis of tetrahydroisoquinoline alkaloids.

Authors:  Thomas Pesnot; Markus C Gershater; John M Ward; Helen C Hailes
Journal:  Chem Commun (Camb)       Date:  2011-01-26       Impact factor: 6.222

2.  Catalytic asymmetric Pictet-Spengler reaction.

Authors:  Jayasree Seayad; Abdul Majeed Seayad; Benjamin List
Journal:  J Am Chem Soc       Date:  2006-02-01       Impact factor: 15.419

3.  Structural basis of enzymatic (S)-norcoclaurine biosynthesis.

Authors:  Andrea Ilari; Stefano Franceschini; Alessandra Bonamore; Fabio Arenghi; Bruno Botta; Alberto Macone; Alessandra Pasquo; Luca Bellucci; Alberto Boffi
Journal:  J Biol Chem       Date:  2008-11-12       Impact factor: 5.157

4.  Enantioselective Friedel-Crafts type addition of indoles to nitro-olefins using a chiral hydrogen-bonding catalyst--synthesis of optically active tetrahydro-beta-carbolines.

Authors:  Wei Zhuang; Rita G Hazell; Karl Anker Jørgensen
Journal:  Org Biomol Chem       Date:  2005-06-21       Impact factor: 3.876

5.  Molecular cloning and characterization of norcoclaurine synthase, an enzyme catalyzing the first committed step in benzylisoquinoline alkaloid biosynthesis.

Authors:  Nailish Samanani; David K Liscombe; Peter J Facchini
Journal:  Plant J       Date:  2004-10       Impact factor: 6.417

6.  Regio- and enantioselective catalytic cyclization of pyrroles onto N-acyliminium ions.

Authors:  Izzat T Raheem; Parvinder S Thiara; Eric N Jacobsen
Journal:  Org Lett       Date:  2008-03-15       Impact factor: 6.005

Review 7.  Muscarinic receptor antagonists for overactive bladder.

Authors:  Paul Abrams; Karl-Erik Andersson
Journal:  BJU Int       Date:  2007-11       Impact factor: 5.588

8.  Anti-HIV michellamines from Ancistrocladus korupensis.

Authors:  M R Boyd; Y F Hallock; J H Cardellina; K P Manfredi; J W Blunt; J B McMahon; R W Buckheit; G Bringmann; M Schäffer; G M Cragg
Journal:  J Med Chem       Date:  1994-06-10       Impact factor: 7.446

9.  Enantioselective BINOL-phosphoric acid catalyzed Pictet-Spengler reactions of N-benzyltryptamine.

Authors:  Nishant V Sewgobind; Martin J Wanner; Steen Ingemann; René de Gelder; Jan H van Maarseveen; Henk Hiemstra
Journal:  J Org Chem       Date:  2008-07-11       Impact factor: 4.354

10.  Beta2-adrenoceptor-mediated tracheal relaxation induced by higenamine from Nandina domestica Thunberg.

Authors:  Muneo Tsukiyama; Takuro Ueki; Yoichi Yasuda; Hiroko Kikuchi; Tatsuhiro Akaishi; Hidenobu Okumura; Kazuho Abe
Journal:  Planta Med       Date:  2009-05-25       Impact factor: 3.352
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  25 in total

1.  Accelerating the semisynthesis of alkaloid-based drugs through metabolic engineering.

Authors:  Amy M Ehrenworth; Pamela Peralta-Yahya
Journal:  Nat Chem Biol       Date:  2017-02-15       Impact factor: 15.040

2.  Peroxisome compartmentalization of a toxic enzyme improves alkaloid production.

Authors:  Parbir S Grewal; Jennifer A Samson; Jordan J Baker; Brian Choi; John E Dueber
Journal:  Nat Chem Biol       Date:  2020-10-12       Impact factor: 15.040

3.  Production of the Carboxylate Reductase from Nocardia otitidiscaviarum in a Soluble, Active Form for in vitro Applications.

Authors:  Douglas Weber; David Patsch; Annika Neumann; Margit Winkler; Dörte Rother
Journal:  Chembiochem       Date:  2021-03-16       Impact factor: 3.164

4.  Asymmetric Preparation of prim-, sec-, and tert-Amines Employing Selected Biocatalysts.

Authors:  Wolfgang Kroutil; Eva-Maria Fischereder; Christine S Fuchs; Horst Lechner; Francesco G Mutti; Desiree Pressnitz; Aashrita Rajagopalan; Johann H Sattler; Robert C Simon; Elina Siirola
Journal:  Org Process Res Dev       Date:  2013-04-22       Impact factor: 3.317

5.  'Dopamine-first' mechanism enables the rational engineering of the norcoclaurine synthase aldehyde activity profile.

Authors:  Benjamin R Lichman; Markus C Gershater; Eleanor D Lamming; Thomas Pesnot; Altin Sula; Nicholas H Keep; Helen C Hailes; John M Ward
Journal:  FEBS J       Date:  2015-02-09       Impact factor: 5.542

6.  Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives.

Authors:  Alejandro A Orden; Joerg H Schrittwieser; Verena Resch; Francesco G Mutti; Wolfgang Kroutil
Journal:  Tetrahedron Asymmetry       Date:  2013-06-30

Review 7.  The role of biocatalysis in the asymmetric synthesis of alkaloids.

Authors:  Joerg H Schrittwieser; Verena Resch
Journal:  RSC Adv       Date:  2013-08-07       Impact factor: 3.361

Review 8.  Building Bridges: Biocatalytic C-C-Bond Formation toward Multifunctional Products.

Authors:  Nina G Schmidt; Elisabeth Eger; Wolfgang Kroutil
Journal:  ACS Catal       Date:  2016-06-08       Impact factor: 13.084

9.  Genes encoding norcoclaurine synthase occur as tandem fusions in the Papaveraceae.

Authors:  Jing Li; Eun-Jeong Lee; Limei Chang; Peter J Facchini
Journal:  Sci Rep       Date:  2016-12-19       Impact factor: 4.379

Review 10.  Green Routes for the Production of Enantiopure Benzylisoquinoline Alkaloids.

Authors:  Francesca Ghirga; Alessandra Bonamore; Lorenzo Calisti; Ilaria D'Acquarica; Mattia Mori; Bruno Botta; Alberto Boffi; Alberto Macone
Journal:  Int J Mol Sci       Date:  2017-11-20       Impact factor: 5.923
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