A nitrilase-mediated entry to 4-carboxymethyl-β-lactams from chemically prepared 4-(cyanomethyl)azetidin-2-ones
- Author
- Lena Decuyper, Nicola Piens (UGent) , Jens Mincke (UGent) , Jeroen Bomon (UGent) , Bert De Schrijver, Karen Mollet (UGent) , Karel De Winter (UGent) , Tom Desmet (UGent) and Matthias D'hooghe (UGent)
- Organization
- Abstract
- (3R, 4S)-3-Alkoxy/aryloxy-4-(cyanomethyl) azetidin-2-ones were efficiently prepared from readily available 1,2: 5,6-di-D-isopropylidene-D-mannitol by means of a classical organic synthesis approach via 4-hydroxymethyl-beta-lactams as key intermediates. The corresponding 4-carboxymethyl-beta-lactams were subsequently obtained after selective hydrolysis of the nitrile functionality by means of a nitrilase enzyme without affecting the sensitive four-membered ring system, hence overcoming the difficulties associated with the chemical hydrolysis approach. Thus, the implementation of a biocatalytic step allows a convenient synthetic route to new 4-carboxymethyl-beta-lactams as versatile building blocks for further elaboration.
- Keywords
- CONDENSED BETA-LACTAMS, CARBAPENEM ANTIBIOTICS, EFFICIENT SYNTHESIS, THERAPEUTIC AGENTS, ACID-DERIVATIVES, GAMMA-LACTONES, RING, THIENAMYCIN, IMINOSUGARS, ROUTE
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-8500765
- MLA
- Decuyper, Lena, et al. “A Nitrilase-Mediated Entry to 4-Carboxymethyl-β-Lactams from Chemically Prepared 4-(Cyanomethyl)Azetidin-2-Ones.” RSC ADVANCES, vol. 6, no. 59, 2016, pp. 54573–79, doi:10.1039/c6ra08213k.
- APA
- Decuyper, L., Piens, N., Mincke, J., Bomon, J., De Schrijver, B., Mollet, K., … D’hooghe, M. (2016). A nitrilase-mediated entry to 4-carboxymethyl-β-lactams from chemically prepared 4-(cyanomethyl)azetidin-2-ones. RSC ADVANCES, 6(59), 54573–54579. https://doi.org/10.1039/c6ra08213k
- Chicago author-date
- Decuyper, Lena, Nicola Piens, Jens Mincke, Jeroen Bomon, Bert De Schrijver, Karen Mollet, Karel De Winter, Tom Desmet, and Matthias D’hooghe. 2016. “A Nitrilase-Mediated Entry to 4-Carboxymethyl-β-Lactams from Chemically Prepared 4-(Cyanomethyl)Azetidin-2-Ones.” RSC ADVANCES 6 (59): 54573–79. https://doi.org/10.1039/c6ra08213k.
- Chicago author-date (all authors)
- Decuyper, Lena, Nicola Piens, Jens Mincke, Jeroen Bomon, Bert De Schrijver, Karen Mollet, Karel De Winter, Tom Desmet, and Matthias D’hooghe. 2016. “A Nitrilase-Mediated Entry to 4-Carboxymethyl-β-Lactams from Chemically Prepared 4-(Cyanomethyl)Azetidin-2-Ones.” RSC ADVANCES 6 (59): 54573–54579. doi:10.1039/c6ra08213k.
- Vancouver
- 1.Decuyper L, Piens N, Mincke J, Bomon J, De Schrijver B, Mollet K, et al. A nitrilase-mediated entry to 4-carboxymethyl-β-lactams from chemically prepared 4-(cyanomethyl)azetidin-2-ones. RSC ADVANCES. 2016;6(59):54573–9.
- IEEE
- [1]L. Decuyper et al., “A nitrilase-mediated entry to 4-carboxymethyl-β-lactams from chemically prepared 4-(cyanomethyl)azetidin-2-ones,” RSC ADVANCES, vol. 6, no. 59, pp. 54573–54579, 2016.
@article{8500765,
abstract = {{(3R, 4S)-3-Alkoxy/aryloxy-4-(cyanomethyl) azetidin-2-ones were efficiently prepared from readily available 1,2: 5,6-di-D-isopropylidene-D-mannitol by means of a classical organic synthesis approach via 4-hydroxymethyl-beta-lactams as key intermediates. The corresponding 4-carboxymethyl-beta-lactams were subsequently obtained after selective hydrolysis of the nitrile functionality by means of a nitrilase enzyme without affecting the sensitive four-membered ring system, hence overcoming the difficulties associated with the chemical hydrolysis approach. Thus, the implementation of a biocatalytic step allows a convenient synthetic route to new 4-carboxymethyl-beta-lactams as versatile building blocks for further elaboration.}},
author = {{Decuyper, Lena and Piens, Nicola and Mincke, Jens and Bomon, Jeroen and De Schrijver, Bert and Mollet, Karen and De Winter, Karel and Desmet, Tom and D'hooghe, Matthias}},
issn = {{2046-2069}},
journal = {{RSC ADVANCES}},
keywords = {{CONDENSED BETA-LACTAMS,CARBAPENEM ANTIBIOTICS,EFFICIENT SYNTHESIS,THERAPEUTIC AGENTS,ACID-DERIVATIVES,GAMMA-LACTONES,RING,THIENAMYCIN,IMINOSUGARS,ROUTE}},
language = {{und}},
number = {{59}},
pages = {{54573--54579}},
title = {{A nitrilase-mediated entry to 4-carboxymethyl-β-lactams from chemically prepared 4-(cyanomethyl)azetidin-2-ones}},
url = {{http://dx.doi.org/10.1039/c6ra08213k}},
volume = {{6}},
year = {{2016}},
}
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