Literature DB >> 27282284

Enantioselective synthesis of cyanohydrins catalysed by hydroxynitrile lyases - a review.

Paula Bracco1, Hanna Busch1, Jan von Langermann2, Ulf Hanefeld1.   

Abstract

The first enantioselective synthesis was the selective addition of cyanide to benzaldehyde catalysed by a hydroxynitrile lyase (HNL). Since then these enzymes have been developed into a reliable tool in organic synthesis. HNLs to prepare either the (R)- or the (S)-enantiomer of the desired cyanohydrin are available and a wide variety of reaction conditions can be applied. As a result of this, numerous applications of these enzymes in organic synthesis have been described. Here the examples of the last decade are summarised, the enzyme catalysed step is discussed and the follow-up chemistry is shown. This proves HNLs to be part of main stream organic synthesis. Additionally the newest approaches via immobilisation and reaction engineering are introduced.

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Year:  2016        PMID: 27282284     DOI: 10.1039/c6ob00934d

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  11 in total

1.  Identical active sites in hydroxynitrile lyases show opposite enantioselectivity and reveal possible ancestral mechanism.

Authors:  Bryan J Jones; Zsófia Bata; Romas J Kazlauskas
Journal:  ACS Catal       Date:  2017-05-15       Impact factor: 13.084

2.  The hydrogenation of mandelonitrile over a Pd/C catalyst: towards a mechanistic understanding.

Authors:  Mairi I McAllister; Cédric Boulho; Liam McMillan; Lauren F Gilpin; Colin Brennan; David Lennon
Journal:  RSC Adv       Date:  2019-08-21       Impact factor: 4.036

Review 3.  Unveiling the functional diversity of the alpha/beta hydrolase superfamily in the plant kingdom.

Authors:  Jeffrey T Mindrebo; Charisse M Nartey; Yoshiya Seto; Michael D Burkart; Joseph P Noel
Journal:  Curr Opin Struct Biol       Date:  2016-09-21       Impact factor: 6.809

4.  Enzyme discovery beyond homology: a unique hydroxynitrile lyase in the Bet v1 superfamily.

Authors:  Elisa Lanfranchi; Tea Pavkov-Keller; Eva-Maria Koehler; Matthias Diepold; Kerstin Steiner; Barbara Darnhofer; Jürgen Hartler; Tom Van Den Bergh; Henk-Jan Joosten; Mandana Gruber-Khadjawi; Gerhard G Thallinger; Ruth Birner-Gruenberger; Karl Gruber; Margit Winkler; Anton Glieder
Journal:  Sci Rep       Date:  2017-05-03       Impact factor: 4.379

5.  Hydroxynitrile lyases from cyanogenic millipedes: molecular cloning, heterologous expression, and whole-cell biocatalysis for the production of (R)-mandelonitrile.

Authors:  Takuya Yamaguchi; Aem Nuylert; Atsutoshi Ina; Tsutomu Tanabe; Yasuhisa Asano
Journal:  Sci Rep       Date:  2018-02-14       Impact factor: 4.379

6.  Catalytic Promiscuity of Galactose Oxidase: A Mild Synthesis of Nitriles from Alcohols, Air, and Ammonia.

Authors:  Jan Vilím; Tanja Knaus; Francesco G Mutti
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-08       Impact factor: 15.336

7.  Value Conflicts in Designing for Safety: Distinguishing Applications of Safe-by-Design and the Inherent Safety Principles.

Authors:  Britte Bouchaut; Lotte Asveld; Ulf Hanefeld; Alexander Vlierboom
Journal:  Int J Environ Res Public Health       Date:  2021-02-18       Impact factor: 3.390

Review 8.  The Hitchhiker's guide to biocatalysis: recent advances in the use of enzymes in organic synthesis.

Authors:  Roger A Sheldon; Dean Brady; Moira L Bode
Journal:  Chem Sci       Date:  2020-02-13       Impact factor: 9.825

9.  R-hydroxynitrile lyase from the cyanogenic millipede, Chamberlinius hualienensis-A new entry to the carrier protein family Lipocalines.

Authors:  Fumihiro Motojima; Atsushi Izumi; Aem Nuylert; Zhenyu Zhai; Mohammad Dadashipour; Sayaka Shichida; Takuya Yamaguchi; Shogo Nakano; Yasuhisa Asano
Journal:  FEBS J       Date:  2020-08-13       Impact factor: 5.542

Review 10.  Applied biocatalysis beyond just buffers - from aqueous to unconventional media. Options and guidelines.

Authors:  Morten M C H van Schie; Jan-Dirk Spöring; Marco Bocola; Pablo Domínguez de María; Dörte Rother
Journal:  Green Chem       Date:  2021-03-26       Impact factor: 10.182

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