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A nitrilase-mediated entry to 4-carboxymethyl-β-lactams from chemically prepared 4-(cyanomethyl)azetidin-2-ones

Lena Decuyper (UGent) , 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)
(2016) RSC ADVANCES. 6(59). p.54573-54579
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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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Chicago
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.
APA
Decuyper, L., Piens, N., Mincke, J., Bomon, J., De Schrijver, B., Mollet, K., De Winter, K., et al. (2016). A nitrilase-mediated entry to 4-carboxymethyl-β-lactams from chemically prepared 4-(cyanomethyl)azetidin-2-ones. RSC ADVANCES, 6(59), 54573–54579.
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.
MLA
Decuyper, Lena, Nicola Piens, Jens Mincke, et al. “A Nitrilase-mediated Entry to 4-carboxymethyl-β-lactams from Chemically Prepared 4-(cyanomethyl)azetidin-2-ones.” RSC ADVANCES 6.59 (2016): 54573–54579. Print.
@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},
  keyword      = {CONDENSED BETA-LACTAMS,CARBAPENEM ANTIBIOTICS,EFFICIENT SYNTHESIS,THERAPEUTIC AGENTS,ACID-DERIVATIVES,GAMMA-LACTONES,RING,THIENAMYCIN,IMINOSUGARS,ROUTE},
  number       = {59},
  pages        = {54573--54579},
  title        = {A nitrilase-mediated entry to 4-carboxymethyl-\ensuremath{\beta}-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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