| 1. |
- Hammer, Stephan C., et al.
(författare)
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Stereoselective Friedel-Crafts alkylation catalyzed by squalene hopene cyclases
- 2012
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Ingår i: Tetrahedron. - : Elsevier Ltd.. - 0040-4020 .- 1464-5416. ; 68:Copyright (C) 2013 American Chemical Society (ACS). All Rights Reserved., s. 7624-7629
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Tidskriftsartikel (refereegranskat)abstract
- In org. synthesis the Friedel-Crafts alkylation is of eminent importance, as it is a key reaction in many synthetic routes. A general access to enzymic Friedel-Crafts alkylations would be very beneficial due to the high selectivity of biocatalysts. We used designed polyprenyl Ph ethers to specifically address this reaction by using squalene hopene cyclases as catalysts. Polycyclic products with arom. rings constituting important biol. active compds. were obtained. Our results demonstrate that squalene hopene cyclases can be utilized for Friedel-Crafts alkylations and reveal the potential of these enzymes for chiral Bronsted acid catalysis.
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| 2. |
- Hammer, Stephan C., et al.
(författare)
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Squalene hopene cyclases : highly promiscuous and evolvable catalysts for stereoselective CC and CX bond formation
- 2013
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Ingår i: Current opinion in chemical biology. - : Elsevier. - 1367-5931 .- 1879-0402. ; 17:2, s. 293-300
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Tidskriftsartikel (refereegranskat)abstract
- A review. We review here how the inherent promiscuous nature, as well as the evolvability of terpene cyclase enzymes enables new applications in chem. We mainly focus on squalene hopene cyclases, class II triterpene synthases that use a proton-initiated cationic polycyclization cascade to form carbopolycyclic products. We highlight recent findings to demonstrate that these enzymes are capable of activating different functionalities other than the traditional terminal isoprene CC-group as well as being compatible with a wide range of nucleophiles beyond the 'ene-functionality'. Thus, squalene hopene cyclases demonstrate a great potential to be used as a toolbox for general Bronsted acid catalysis.
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| 3. |
- Nebel, Bernd A., et al.
(författare)
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A Career in Catalysis : Bernhard Hauer
- 2023
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Ingår i: ACS Catalysis. - : American Chemical Society (ACS). - 2155-5435 .- 2155-5435. ; 13:13, s. 8861-8889
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Forskningsöversikt (refereegranskat)abstract
- On the occasion of Professor Bernhard Hauer′s (partial) retirement, we reflect on and highlight his distinguished career in biocatalysis. Bernhard, a biologist by training, has greatly influenced biocatalysis with his vision and ideas throughout his four-decade career. The development of his career went hand in hand with the evolution of biocatalysis and the application and development of enzymes for chemical processes. In this Account, we present selected examples of his early work on the development of enzymes and their application in an industrial setting, with a focus on his specific contributions to harnessing the catalytic power of enzymes for novel reactions and the understanding and engineering of flexible loops and channels on catalysis.
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| 4. |
- Seitz, Miriam, et al.
(författare)
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Synthesis of Heterocyclic Terpenoids by Promiscuous Squalene-Hopene Cyclases
- 2013
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Ingår i: ChemBioChem (Print). - : Wiley-VCH Verlag GmbH & Co. KGaA. - 1439-4227 .- 1439-7633. ; 14:Copyright (C) 2013 American Chemical Society (ACS). All Rights Reserved., s. 436-439
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Tidskriftsartikel (refereegranskat)abstract
- Promiscuous enzymes: The substrate promiscuity of squalene–hopene cyclases has been explored and applied in the enzyme‐catalyzed synthesis of heterocyclic terpenoids. Features of this work include cyclization reactions without pyrophosphate activation, and stereospecific ring closure of substrates of varying chain length and terminal nucleophile. This provides a biocatalytic alternative to traditional chemical catalysts.
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