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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, Jens Mincke UGent, Jeroen Bomon, Bert De Schrijver, Karen Mollet, Karel De Winter, Tom Desmet UGent and Matthias D'hooghe UGent (2016) RSC ADVANCES. 6(59). p.54573-54579
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.
Please use this url to cite or link to this publication:
author
organization
alternative title
A nitrilase-mediated entry to 4-carboxymethyl-beta-lactams from chemically prepared 4-(cyanomethyl)azetidin-2-ones
year
type
journalArticle (original)
publication status
published
subject
keyword
CONDENSED BETA-LACTAMS, CARBAPENEM ANTIBIOTICS, EFFICIENT SYNTHESIS, THERAPEUTIC AGENTS, ACID-DERIVATIVES, GAMMA-LACTONES, RING, THIENAMYCIN, IMINOSUGARS, ROUTE
journal title
RSC ADVANCES
RSC Adv.
volume
6
issue
59
pages
54573 - 54579
Web of Science type
Article
Web of Science id
000378521400119
JCR category
CHEMISTRY, MULTIDISCIPLINARY
JCR impact factor
3.108 (2016)
JCR rank
59/166 (2016)
JCR quartile
2 (2016)
ISSN
2046-2069
DOI
10.1039/c6ra08213k
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
8500765
handle
http://hdl.handle.net/1854/LU-8500765
date created
2017-01-09 11:49:50
date last changed
2018-01-03 23:30:23
@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},
}

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.