A nitrilase-mediated entry to 4-carboxymethyl-β-lactams from chemically prepared 4-(cyanomethyl)azetidin-2-ones
(3 R ,4 S )-3-Alkoxy/aryloxy-4-(cyanomethyl)azetidin-2-ones were efficiently prepared from readily available 1,2:5,6-di- O -isopropylidene- d -mannitol by means of a classical organic synthesis approach via 4-hydroxymethyl-β-lactams as key intermediates. The corresponding 4-carboxymethyl-β-lactams w...
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| Veröffentlicht in: | RSC advances 2016-01, Vol.6 (59), p.54573-54579 |
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| container_issue | 59 |
| container_start_page | 54573 |
| container_title | RSC advances |
| container_volume | 6 |
| creator | Decuyper, Lena Piens, Nicola Mincke, Jens Bomon, Jeroen De Schrijver, Bert Mollet, Karen De Winter, Karel Desmet, Tom D'hooghe, Matthias |
| description | (3
R
,4
S
)-3-Alkoxy/aryloxy-4-(cyanomethyl)azetidin-2-ones were efficiently prepared from readily available 1,2:5,6-di-
O
-isopropylidene-
d
-mannitol by means of a classical organic synthesis approach
via
4-hydroxymethyl-β-lactams as key intermediates. The corresponding 4-carboxymethyl-β-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-β-lactams as versatile building blocks for further elaboration.
4-(Cyanomethyl)azetidin-2-ones were efficiently prepared from 1,2:5,6-di-
O
-isopropylidene-
d
-mannitol, followed by a nitrilase-catalyzed hydrolysis to 4-carboxymethyl β-lactams without affecting the sensitive four-membered ring system. |
| doi_str_mv | 10.1039/c6ra08213k |
| format | Article |
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R
,4
S
)-3-Alkoxy/aryloxy-4-(cyanomethyl)azetidin-2-ones were efficiently prepared from readily available 1,2:5,6-di-
O
-isopropylidene-
d
-mannitol by means of a classical organic synthesis approach
via
4-hydroxymethyl-β-lactams as key intermediates. The corresponding 4-carboxymethyl-β-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-β-lactams as versatile building blocks for further elaboration.
4-(Cyanomethyl)azetidin-2-ones were efficiently prepared from 1,2:5,6-di-
O
-isopropylidene-
d
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R
,4
S
)-3-Alkoxy/aryloxy-4-(cyanomethyl)azetidin-2-ones were efficiently prepared from readily available 1,2:5,6-di-
O
-isopropylidene-
d
-mannitol by means of a classical organic synthesis approach
via
4-hydroxymethyl-β-lactams as key intermediates. The corresponding 4-carboxymethyl-β-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-β-lactams as versatile building blocks for further elaboration.
4-(Cyanomethyl)azetidin-2-ones were efficiently prepared from 1,2:5,6-di-
O
-isopropylidene-
d
-mannitol, followed by a nitrilase-catalyzed hydrolysis to 4-carboxymethyl β-lactams without affecting the sensitive four-membered ring system.</description><subject>Enzymes</subject><subject>Hydrolysis</subject><subject>Nitriles</subject><subject>Synthesis</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNpNkMlKxEAURYMo2LRu3AtZtkJpjRmWTeOEDYLoOrxUXujSymBVNRg_yw_xm4xG1Le5b3HuXZwoOmL0jFGRn-vEAc04E8870YxTmRBOk3z3378fHXr_RMdLFOMJm0X9Mm5NcMaCR9JgZSBgFWMb3BCHLpZEgyu716HBsBks-XgnFnSAxse165pYb7AxGqwd4t5hD24sS7LQA7TdVDmBNwymMi3hpGvRH0R7NViPhz85jx4vLx5W12R9d3WzWq6JFpwHglgB8lpWAvNalFmJkGssk6qiPE9TUEpCijUoWTFVp6hrJaSGXApVJiLTYh4tpt3edS9b9KFojNdoLbTYbX3BMq4UEzIXI3o6odp13jusi96ZBtxQMFp8mS1Wyf3y2-ztCB9PsPP6l_szLz4BASx4cw</recordid><startdate>20160101</startdate><enddate>20160101</enddate><creator>Decuyper, Lena</creator><creator>Piens, Nicola</creator><creator>Mincke, Jens</creator><creator>Bomon, Jeroen</creator><creator>De Schrijver, Bert</creator><creator>Mollet, Karen</creator><creator>De Winter, Karel</creator><creator>Desmet, Tom</creator><creator>D'hooghe, Matthias</creator><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20160101</creationdate><title>A nitrilase-mediated entry to 4-carboxymethyl-β-lactams from chemically prepared 4-(cyanomethyl)azetidin-2-ones</title><author>Decuyper, Lena ; Piens, Nicola ; Mincke, Jens ; Bomon, Jeroen ; De Schrijver, Bert ; Mollet, Karen ; De Winter, Karel ; Desmet, Tom ; D'hooghe, Matthias</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c322t-eedae2f4d3e9f3b8bea9ceb6dd02977a554a7efa54d15f7ecf534ca9435b638c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Enzymes</topic><topic>Hydrolysis</topic><topic>Nitriles</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Decuyper, Lena</creatorcontrib><creatorcontrib>Piens, Nicola</creatorcontrib><creatorcontrib>Mincke, Jens</creatorcontrib><creatorcontrib>Bomon, Jeroen</creatorcontrib><creatorcontrib>De Schrijver, Bert</creatorcontrib><creatorcontrib>Mollet, Karen</creatorcontrib><creatorcontrib>De Winter, Karel</creatorcontrib><creatorcontrib>Desmet, Tom</creatorcontrib><creatorcontrib>D'hooghe, Matthias</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Decuyper, Lena</au><au>Piens, Nicola</au><au>Mincke, Jens</au><au>Bomon, Jeroen</au><au>De Schrijver, Bert</au><au>Mollet, Karen</au><au>De Winter, Karel</au><au>Desmet, Tom</au><au>D'hooghe, Matthias</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A nitrilase-mediated entry to 4-carboxymethyl-β-lactams from chemically prepared 4-(cyanomethyl)azetidin-2-ones</atitle><jtitle>RSC advances</jtitle><date>2016-01-01</date><risdate>2016</risdate><volume>6</volume><issue>59</issue><spage>54573</spage><epage>54579</epage><pages>54573-54579</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>(3
R
,4
S
)-3-Alkoxy/aryloxy-4-(cyanomethyl)azetidin-2-ones were efficiently prepared from readily available 1,2:5,6-di-
O
-isopropylidene-
d
-mannitol by means of a classical organic synthesis approach
via
4-hydroxymethyl-β-lactams as key intermediates. The corresponding 4-carboxymethyl-β-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-β-lactams as versatile building blocks for further elaboration.
4-(Cyanomethyl)azetidin-2-ones were efficiently prepared from 1,2:5,6-di-
O
-isopropylidene-
d
-mannitol, followed by a nitrilase-catalyzed hydrolysis to 4-carboxymethyl β-lactams without affecting the sensitive four-membered ring system.</abstract><doi>10.1039/c6ra08213k</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
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| ispartof | RSC advances, 2016-01, Vol.6 (59), p.54573-54579 |
| issn | 2046-2069 2046-2069 |
| language | eng |
| recordid | cdi_rsc_primary_c6ra08213k |
| source | Royal Society Of Chemistry Journals |
| subjects | Enzymes Hydrolysis Nitriles Synthesis |
| title | A nitrilase-mediated entry to 4-carboxymethyl-β-lactams from chemically prepared 4-(cyanomethyl)azetidin-2-ones |
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