The anomalous course of the microsomal transformation of the exo-2,3-epoxides of norbornene and norbornadiene. The possible involvement of a general acid activation during the enzymatic hydrolysis of these oxides
The enzymatic hydrolysis of exo-2,3-epoxy-norbornane ( 1) with a crude rabbit liver microsomal preparation occurred with a rearrangement and gave selectively (2 R,7 S)-bicyclo[2.2.1]heptane-2,7-diol ( 3) , enantiomeric excess (ee) 30±2%. The analogous exo-2,3-epoxy-5-norbornene ( 2) gave, under the...
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| Veröffentlicht in: | Journal of molecular catalysis. B, Enzymatic Enzymatic, 2000-10, Vol.10 (5), p.539-544 |
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| container_end_page | 544 |
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| container_issue | 5 |
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| container_title | Journal of molecular catalysis. B, Enzymatic |
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| creator | Chiappe, Cinzia De Rubertis, Antonietta Marioni, Franco Simonetti, Alberto |
| description | The enzymatic hydrolysis of
exo-2,3-epoxy-norbornane (
1)
with a crude rabbit liver microsomal preparation occurred with a rearrangement and gave selectively
(2
R,7
S)-bicyclo[2.2.1]heptane-2,7-diol (
3)
, enantiomeric excess (ee) 30±2%. The analogous
exo-2,3-epoxy-5-norbornene (
2)
gave, under the same conditions, exclusively
endo-6-hydroxymethylbicyclo[3.1.0]hex-2-ene (
4)
, arising from the microsomal catalyzed reduction of the first formed
endo-6-formylbicyclo[3.1.0]hex-2-ene (
5)
. A mechanistic explanation for the observed products is proposed. |
| doi_str_mv | 10.1016/S1381-1177(00)00097-7 |
| format | Article |
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exo-2,3-epoxy-norbornane (
1)
with a crude rabbit liver microsomal preparation occurred with a rearrangement and gave selectively
(2
R,7
S)-bicyclo[2.2.1]heptane-2,7-diol (
3)
, enantiomeric excess (ee) 30±2%. The analogous
exo-2,3-epoxy-5-norbornene (
2)
gave, under the same conditions, exclusively
endo-6-hydroxymethylbicyclo[3.1.0]hex-2-ene (
4)
, arising from the microsomal catalyzed reduction of the first formed
endo-6-formylbicyclo[3.1.0]hex-2-ene (
5)
. A mechanistic explanation for the observed products is proposed.</description><identifier>ISSN: 1381-1177</identifier><identifier>EISSN: 1873-3158</identifier><identifier>DOI: 10.1016/S1381-1177(00)00097-7</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Bioconversion ; Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; Catalysis ; Catalyst selectivity ; Fundamental and applied biological sciences. Psychology ; Hydrolysis ; mEH ; Methods. Procedures. Technologies ; Microsomal biotransformation ; Reaction kinetics ; Reaction mechanism ; Reduction</subject><ispartof>Journal of molecular catalysis. B, Enzymatic, 2000-10, Vol.10 (5), p.539-544</ispartof><rights>2000 Elsevier Science B.V.</rights><rights>2000 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c367t-8d21dc26f8b6d648ef6020b8b8adf0e928a4d611f600bac6cf9014ab76446da73</citedby><cites>FETCH-LOGICAL-c367t-8d21dc26f8b6d648ef6020b8b8adf0e928a4d611f600bac6cf9014ab76446da73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S1381-1177(00)00097-7$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27923,27924,45994</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1521082$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Chiappe, Cinzia</creatorcontrib><creatorcontrib>De Rubertis, Antonietta</creatorcontrib><creatorcontrib>Marioni, Franco</creatorcontrib><creatorcontrib>Simonetti, Alberto</creatorcontrib><title>The anomalous course of the microsomal transformation of the exo-2,3-epoxides of norbornene and norbornadiene. The possible involvement of a general acid activation during the enzymatic hydrolysis of these oxides</title><title>Journal of molecular catalysis. B, Enzymatic</title><description>The enzymatic hydrolysis of
exo-2,3-epoxy-norbornane (
1)
with a crude rabbit liver microsomal preparation occurred with a rearrangement and gave selectively
(2
R,7
S)-bicyclo[2.2.1]heptane-2,7-diol (
3)
, enantiomeric excess (ee) 30±2%. The analogous
exo-2,3-epoxy-5-norbornene (
2)
gave, under the same conditions, exclusively
endo-6-hydroxymethylbicyclo[3.1.0]hex-2-ene (
4)
, arising from the microsomal catalyzed reduction of the first formed
endo-6-formylbicyclo[3.1.0]hex-2-ene (
5)
. A mechanistic explanation for the observed products is proposed.</description><subject>Bioconversion</subject><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Catalysis</subject><subject>Catalyst selectivity</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hydrolysis</subject><subject>mEH</subject><subject>Methods. Procedures. Technologies</subject><subject>Microsomal biotransformation</subject><subject>Reaction kinetics</subject><subject>Reaction mechanism</subject><subject>Reduction</subject><issn>1381-1177</issn><issn>1873-3158</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><recordid>eNqFUU1v1DAQjRBIlMJPQMoBIZCa4nGyjveEqgoKUiUOlLPl2OPWKLEXT3bV5Xfyg7A3u-LIxR_Pb-Y9z6uq18AugYH48B1aCQ1A379j7D1jbN03_ZPqDGTfNi2s5NN8PlGeVy-IfmYSB5Bn1Z-7B6x1iJMe45ZqE7eJsI6unjM-eZMilbd6TjqQi2nSs4_hRMDH2PCLtsFNfPQWqeAhpiGmgKH0taertj4jl3WR20QiP4xY-7CL4w4nDHOp1PV95qSspo23eZn9bpGz2-TD_SIZfu-LCVM_7G2K4548He0U4wcbL6tnTo-Er477efXj86e76y_N7bebr9dXt41pRT830nKwhgsnB2FFJ9EJxtkgB6mtY7jmUndWAGSYDdoI49YMOj30ouuE1X17Xr1d-m5S_LVFmtXkyeA46oB5mopDx9et5Jm4WohlnpTQqU3yk057BUyVDNUhQ1UCUoypQ4aqCLw5CmgyenQ5BOPpX_GKAzu0_7jQMH925zEpMnncBq1PaGZlo_-P0F-mZLZo</recordid><startdate>20001002</startdate><enddate>20001002</enddate><creator>Chiappe, Cinzia</creator><creator>De Rubertis, Antonietta</creator><creator>Marioni, Franco</creator><creator>Simonetti, Alberto</creator><general>Elsevier B.V</general><general>Elsevier Science</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20001002</creationdate><title>The anomalous course of the microsomal transformation of the exo-2,3-epoxides of norbornene and norbornadiene. The possible involvement of a general acid activation during the enzymatic hydrolysis of these oxides</title><author>Chiappe, Cinzia ; De Rubertis, Antonietta ; Marioni, Franco ; Simonetti, Alberto</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c367t-8d21dc26f8b6d648ef6020b8b8adf0e928a4d611f600bac6cf9014ab76446da73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Bioconversion</topic><topic>Bioconversions. Hemisynthesis</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Catalysis</topic><topic>Catalyst selectivity</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Hydrolysis</topic><topic>mEH</topic><topic>Methods. Procedures. Technologies</topic><topic>Microsomal biotransformation</topic><topic>Reaction kinetics</topic><topic>Reaction mechanism</topic><topic>Reduction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chiappe, Cinzia</creatorcontrib><creatorcontrib>De Rubertis, Antonietta</creatorcontrib><creatorcontrib>Marioni, Franco</creatorcontrib><creatorcontrib>Simonetti, Alberto</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Journal of molecular catalysis. B, Enzymatic</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chiappe, Cinzia</au><au>De Rubertis, Antonietta</au><au>Marioni, Franco</au><au>Simonetti, Alberto</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The anomalous course of the microsomal transformation of the exo-2,3-epoxides of norbornene and norbornadiene. The possible involvement of a general acid activation during the enzymatic hydrolysis of these oxides</atitle><jtitle>Journal of molecular catalysis. B, Enzymatic</jtitle><date>2000-10-02</date><risdate>2000</risdate><volume>10</volume><issue>5</issue><spage>539</spage><epage>544</epage><pages>539-544</pages><issn>1381-1177</issn><eissn>1873-3158</eissn><abstract>The enzymatic hydrolysis of
exo-2,3-epoxy-norbornane (
1)
with a crude rabbit liver microsomal preparation occurred with a rearrangement and gave selectively
(2
R,7
S)-bicyclo[2.2.1]heptane-2,7-diol (
3)
, enantiomeric excess (ee) 30±2%. The analogous
exo-2,3-epoxy-5-norbornene (
2)
gave, under the same conditions, exclusively
endo-6-hydroxymethylbicyclo[3.1.0]hex-2-ene (
4)
, arising from the microsomal catalyzed reduction of the first formed
endo-6-formylbicyclo[3.1.0]hex-2-ene (
5)
. A mechanistic explanation for the observed products is proposed.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><doi>10.1016/S1381-1177(00)00097-7</doi><tpages>6</tpages></addata></record> |
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| ispartof | Journal of molecular catalysis. B, Enzymatic, 2000-10, Vol.10 (5), p.539-544 |
| issn | 1381-1177 1873-3158 |
| language | eng |
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| source | ScienceDirect Journals (5 years ago - present) |
| subjects | Bioconversion Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Catalysis Catalyst selectivity Fundamental and applied biological sciences. Psychology Hydrolysis mEH Methods. Procedures. Technologies Microsomal biotransformation Reaction kinetics Reaction mechanism Reduction |
| title | The anomalous course of the microsomal transformation of the exo-2,3-epoxides of norbornene and norbornadiene. The possible involvement of a general acid activation during the enzymatic hydrolysis of these oxides |
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