Loading…
(R)-Oxynitrilase-catalysed synthesis of chiral silicon-containing aliphatic (R)-ketone-cyanohydrins
Optically active 2-trimethylsilyl-2-hydroxyl-ethylcyanide was prepared by enzymatic enantioselective transcyanation of acetyltrimethylsilane with acetone cyanohydrin in a biphasic system at 35 degrees C and pH 5. (R)-Oxynitrilase from apple seed meal was the best among all the enzymes explored and d...
Saved in:
| Published in: | Biotechnology letters 2003-02, Vol.25 (3), p.219-222 |
|---|---|
| Main Authors: | , , , , |
| Format: | Article |
| Language: | English |
| Subjects: | |
| Citations: | Items that cite this one |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| cited_by | cdi_FETCH-LOGICAL-c341t-d552355bf44b9ecac8e962916495a66c164aa54abf50085da0eef3f111aed5623 |
|---|---|
| cites | |
| container_end_page | 222 |
| container_issue | 3 |
| container_start_page | 219 |
| container_title | Biotechnology letters |
| container_volume | 25 |
| creator | NING LI ZONG, Min-Hua CHEN LIU PENG, Hua-Song WU, Hua-Chang |
| description | Optically active 2-trimethylsilyl-2-hydroxyl-ethylcyanide was prepared by enzymatic enantioselective transcyanation of acetyltrimethylsilane with acetone cyanohydrin in a biphasic system at 35 degrees C and pH 5. (R)-Oxynitrilase from apple seed meal was the best among all the enzymes explored and diisopropyl ether was the most suitable organic phase. Acetyltrimethylsilane was a better substrate of the enzyme than its carbon analogue. The substrate conversion and product enantiomeric excess of 2-trimethylsilyl-2-hydroxyl-ethylcyanide were >99% and >99%, respectively. |
| doi_str_mv | 10.1023/A:1022316919552 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_proquest_miscellaneous_73500614</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>18719297</sourcerecordid><originalsourceid>FETCH-LOGICAL-c341t-d552355bf44b9ecac8e962916495a66c164aa54abf50085da0eef3f111aed5623</originalsourceid><addsrcrecordid>eNqFkctLxDAQh4Mouj7O3qQIih6qmTwbb4v4AkEQPS-zaepGs-nadMH-90ZcEbx4GH5z-OaDmSFkH-gZUMbPxxc5GAdlwEjJ1sgIpOal0lqtkxEFAaUUhm2R7ZReKaVGU71JtoBVFZNajIg9eTwtHz6G6PvOB0yutNhjGJKrizTEfuaST0XbFHbmOwxF8sHbNpa5evTRx5cCg1_MsPe2-HK9ub6N2TJgbGdD3fmYdslGgyG5vVXukOfrq6fL2_L-4ebucnxfWi6gL-u8AJdy2ggxNc6irZxRzIASRqJSNjeIUuC0kZRWskbqXMMbAEBXS8X4Djn-9i669n3pUj-Z-2RdCBhdu0wTzfOgAvEvCJUGw4zO4OEf8LVddjEvkWWiqrgRPEMHK2g5nbt6suj8HLth8nPkDBytAEwWQ9NhtD79ciK_izLgn25ziyc</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>734883943</pqid></control><display><type>article</type><title>(R)-Oxynitrilase-catalysed synthesis of chiral silicon-containing aliphatic (R)-ketone-cyanohydrins</title><source>Springer Nature</source><creator>NING LI ; ZONG, Min-Hua ; CHEN LIU ; PENG, Hua-Song ; WU, Hua-Chang</creator><creatorcontrib>NING LI ; ZONG, Min-Hua ; CHEN LIU ; PENG, Hua-Song ; WU, Hua-Chang</creatorcontrib><description>Optically active 2-trimethylsilyl-2-hydroxyl-ethylcyanide was prepared by enzymatic enantioselective transcyanation of acetyltrimethylsilane with acetone cyanohydrin in a biphasic system at 35 degrees C and pH 5. (R)-Oxynitrilase from apple seed meal was the best among all the enzymes explored and diisopropyl ether was the most suitable organic phase. Acetyltrimethylsilane was a better substrate of the enzyme than its carbon analogue. The substrate conversion and product enantiomeric excess of 2-trimethylsilyl-2-hydroxyl-ethylcyanide were >99% and >99%, respectively.</description><identifier>ISSN: 0141-5492</identifier><identifier>EISSN: 1573-6776</identifier><identifier>DOI: 10.1023/A:1022316919552</identifier><identifier>PMID: 12882574</identifier><identifier>CODEN: BILED3</identifier><language>eng</language><publisher>Dordrecht: Springer</publisher><subject>Aldehyde-Lyases - chemistry ; Biological and medical sciences ; Catalysis ; Chemical synthesis ; Fundamental and applied biological sciences. Psychology ; Hydrogen-Ion Concentration ; Ketones - chemistry ; Malus - chemistry ; Malus - enzymology ; Nitriles - chemical synthesis ; Nitriles - chemistry ; Seeds - chemistry ; Seeds - enzymology ; Silicon ; Silicon - chemistry ; Stereoisomerism ; Substrate Specificity ; Temperature ; Trimethylsilyl Compounds - chemical synthesis ; Trimethylsilyl Compounds - chemistry</subject><ispartof>Biotechnology letters, 2003-02, Vol.25 (3), p.219-222</ispartof><rights>2003 INIST-CNRS</rights><rights>Kluwer Academic Publishers 2003</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c341t-d552355bf44b9ecac8e962916495a66c164aa54abf50085da0eef3f111aed5623</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14677021$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12882574$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>NING LI</creatorcontrib><creatorcontrib>ZONG, Min-Hua</creatorcontrib><creatorcontrib>CHEN LIU</creatorcontrib><creatorcontrib>PENG, Hua-Song</creatorcontrib><creatorcontrib>WU, Hua-Chang</creatorcontrib><title>(R)-Oxynitrilase-catalysed synthesis of chiral silicon-containing aliphatic (R)-ketone-cyanohydrins</title><title>Biotechnology letters</title><addtitle>Biotechnol Lett</addtitle><description>Optically active 2-trimethylsilyl-2-hydroxyl-ethylcyanide was prepared by enzymatic enantioselective transcyanation of acetyltrimethylsilane with acetone cyanohydrin in a biphasic system at 35 degrees C and pH 5. (R)-Oxynitrilase from apple seed meal was the best among all the enzymes explored and diisopropyl ether was the most suitable organic phase. Acetyltrimethylsilane was a better substrate of the enzyme than its carbon analogue. The substrate conversion and product enantiomeric excess of 2-trimethylsilyl-2-hydroxyl-ethylcyanide were >99% and >99%, respectively.</description><subject>Aldehyde-Lyases - chemistry</subject><subject>Biological and medical sciences</subject><subject>Catalysis</subject><subject>Chemical synthesis</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hydrogen-Ion Concentration</subject><subject>Ketones - chemistry</subject><subject>Malus - chemistry</subject><subject>Malus - enzymology</subject><subject>Nitriles - chemical synthesis</subject><subject>Nitriles - chemistry</subject><subject>Seeds - chemistry</subject><subject>Seeds - enzymology</subject><subject>Silicon</subject><subject>Silicon - chemistry</subject><subject>Stereoisomerism</subject><subject>Substrate Specificity</subject><subject>Temperature</subject><subject>Trimethylsilyl Compounds - chemical synthesis</subject><subject>Trimethylsilyl Compounds - chemistry</subject><issn>0141-5492</issn><issn>1573-6776</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><recordid>eNqFkctLxDAQh4Mouj7O3qQIih6qmTwbb4v4AkEQPS-zaepGs-nadMH-90ZcEbx4GH5z-OaDmSFkH-gZUMbPxxc5GAdlwEjJ1sgIpOal0lqtkxEFAaUUhm2R7ZReKaVGU71JtoBVFZNajIg9eTwtHz6G6PvOB0yutNhjGJKrizTEfuaST0XbFHbmOwxF8sHbNpa5evTRx5cCg1_MsPe2-HK9ub6N2TJgbGdD3fmYdslGgyG5vVXukOfrq6fL2_L-4ebucnxfWi6gL-u8AJdy2ggxNc6irZxRzIASRqJSNjeIUuC0kZRWskbqXMMbAEBXS8X4Djn-9i669n3pUj-Z-2RdCBhdu0wTzfOgAvEvCJUGw4zO4OEf8LVddjEvkWWiqrgRPEMHK2g5nbt6suj8HLth8nPkDBytAEwWQ9NhtD79ciK_izLgn25ziyc</recordid><startdate>20030201</startdate><enddate>20030201</enddate><creator>NING LI</creator><creator>ZONG, Min-Hua</creator><creator>CHEN LIU</creator><creator>PENG, Hua-Song</creator><creator>WU, Hua-Chang</creator><general>Springer</general><general>Springer Nature B.V</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>3V.</scope><scope>7QL</scope><scope>7QR</scope><scope>7T7</scope><scope>7TB</scope><scope>7U5</scope><scope>7X7</scope><scope>7XB</scope><scope>88A</scope><scope>88E</scope><scope>88I</scope><scope>8AO</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>L6V</scope><scope>L7M</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7N</scope><scope>M7P</scope><scope>M7S</scope><scope>P64</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PTHSS</scope><scope>Q9U</scope><scope>7QO</scope><scope>7X8</scope></search><sort><creationdate>20030201</creationdate><title>(R)-Oxynitrilase-catalysed synthesis of chiral silicon-containing aliphatic (R)-ketone-cyanohydrins</title><author>NING LI ; ZONG, Min-Hua ; CHEN LIU ; PENG, Hua-Song ; WU, Hua-Chang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c341t-d552355bf44b9ecac8e962916495a66c164aa54abf50085da0eef3f111aed5623</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Aldehyde-Lyases - chemistry</topic><topic>Biological and medical sciences</topic><topic>Catalysis</topic><topic>Chemical synthesis</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Hydrogen-Ion Concentration</topic><topic>Ketones - chemistry</topic><topic>Malus - chemistry</topic><topic>Malus - enzymology</topic><topic>Nitriles - chemical synthesis</topic><topic>Nitriles - chemistry</topic><topic>Seeds - chemistry</topic><topic>Seeds - enzymology</topic><topic>Silicon</topic><topic>Silicon - chemistry</topic><topic>Stereoisomerism</topic><topic>Substrate Specificity</topic><topic>Temperature</topic><topic>Trimethylsilyl Compounds - chemical synthesis</topic><topic>Trimethylsilyl Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>NING LI</creatorcontrib><creatorcontrib>ZONG, Min-Hua</creatorcontrib><creatorcontrib>CHEN LIU</creatorcontrib><creatorcontrib>PENG, Hua-Song</creatorcontrib><creatorcontrib>WU, Hua-Chang</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>ProQuest Central (Corporate)</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Chemoreception Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Biology Database (Alumni Edition)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central</collection><collection>Engineering Research Database</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>ProQuest Engineering Collection</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>ProQuest Biological Science Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Science Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>ProQuest Biological Science Journals</collection><collection>Engineering Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>Engineering collection</collection><collection>ProQuest Central Basic</collection><collection>Biotechnology Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Biotechnology letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>NING LI</au><au>ZONG, Min-Hua</au><au>CHEN LIU</au><au>PENG, Hua-Song</au><au>WU, Hua-Chang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>(R)-Oxynitrilase-catalysed synthesis of chiral silicon-containing aliphatic (R)-ketone-cyanohydrins</atitle><jtitle>Biotechnology letters</jtitle><addtitle>Biotechnol Lett</addtitle><date>2003-02-01</date><risdate>2003</risdate><volume>25</volume><issue>3</issue><spage>219</spage><epage>222</epage><pages>219-222</pages><issn>0141-5492</issn><eissn>1573-6776</eissn><coden>BILED3</coden><abstract>Optically active 2-trimethylsilyl-2-hydroxyl-ethylcyanide was prepared by enzymatic enantioselective transcyanation of acetyltrimethylsilane with acetone cyanohydrin in a biphasic system at 35 degrees C and pH 5. (R)-Oxynitrilase from apple seed meal was the best among all the enzymes explored and diisopropyl ether was the most suitable organic phase. Acetyltrimethylsilane was a better substrate of the enzyme than its carbon analogue. The substrate conversion and product enantiomeric excess of 2-trimethylsilyl-2-hydroxyl-ethylcyanide were >99% and >99%, respectively.</abstract><cop>Dordrecht</cop><pub>Springer</pub><pmid>12882574</pmid><doi>10.1023/A:1022316919552</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0141-5492 |
| ispartof | Biotechnology letters, 2003-02, Vol.25 (3), p.219-222 |
| issn | 0141-5492 1573-6776 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_73500614 |
| source | Springer Nature |
| subjects | Aldehyde-Lyases - chemistry Biological and medical sciences Catalysis Chemical synthesis Fundamental and applied biological sciences. Psychology Hydrogen-Ion Concentration Ketones - chemistry Malus - chemistry Malus - enzymology Nitriles - chemical synthesis Nitriles - chemistry Seeds - chemistry Seeds - enzymology Silicon Silicon - chemistry Stereoisomerism Substrate Specificity Temperature Trimethylsilyl Compounds - chemical synthesis Trimethylsilyl Compounds - chemistry |
| title | (R)-Oxynitrilase-catalysed synthesis of chiral silicon-containing aliphatic (R)-ketone-cyanohydrins |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T14%3A50%3A38IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=(R)-Oxynitrilase-catalysed%20synthesis%20of%20chiral%20silicon-containing%20aliphatic%20(R)-ketone-cyanohydrins&rft.jtitle=Biotechnology%20letters&rft.au=NING%20LI&rft.date=2003-02-01&rft.volume=25&rft.issue=3&rft.spage=219&rft.epage=222&rft.pages=219-222&rft.issn=0141-5492&rft.eissn=1573-6776&rft.coden=BILED3&rft_id=info:doi/10.1023/A:1022316919552&rft_dat=%3Cproquest_pubme%3E18719297%3C/proquest_pubme%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c341t-d552355bf44b9ecac8e962916495a66c164aa54abf50085da0eef3f111aed5623%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=734883943&rft_id=info:pmid/12882574&rfr_iscdi=true |