Chemoenzymatic routes to enantiomerically pure 2-azatyrosine and 2-, 3- and 4-pyridylalanine derivatives
Enantiomerically pure 2-, 3- or 4-pyridylalanine (pya) and 2-azatyrosine (azatyr) are known to present various biological activities. After incorporation into appropriate peptide sequences, these heterocyclic non natural α-amino acids could behave as new substrates or inhibitors of elastase from Pse...
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| Veröffentlicht in: | Amino acids 2012-04, Vol.42 (4), p.1339-1348 |
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| container_title | Amino acids |
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| creator | Moussa, Amer Meffre, Patrick Martinez, Jean Rolland, Valérie |
| description | Enantiomerically pure 2-, 3- or 4-pyridylalanine (pya) and 2-azatyrosine (azatyr) are known to present various biological activities. After incorporation into appropriate peptide sequences, these heterocyclic non natural α-amino acids could behave as new substrates or inhibitors of elastase from
Pseudomonas aeruginosa
. This enzyme is known to be involved in nosocomial infections and infections related to the cystic fibrosis disease. New efficient chemoenzymatic preparations of those compounds using α-chymotrypsin (α-CT) are presented. |
| doi_str_mv | 10.1007/s00726-010-0829-3 |
| format | Article |
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Pseudomonas aeruginosa
. This enzyme is known to be involved in nosocomial infections and infections related to the cystic fibrosis disease. New efficient chemoenzymatic preparations of those compounds using α-chymotrypsin (α-CT) are presented.</description><identifier>ISSN: 0939-4451</identifier><identifier>EISSN: 1438-2199</identifier><identifier>DOI: 10.1007/s00726-010-0829-3</identifier><identifier>PMID: 21279396</identifier><language>eng</language><publisher>Vienna: Springer Vienna</publisher><subject>Alanine - analogs & derivatives ; Alanine - chemical synthesis ; Alanine - chemistry ; Alanine - pharmacology ; Amino acids ; Analytical Chemistry ; Biochemical Engineering ; Biochemistry ; Biomedical and Life Sciences ; Catalysis ; Chemical Sciences ; Chymotrypsin - antagonists & inhibitors ; Cystic fibrosis ; Derivatives ; Elastase ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Enzymes ; Inhibitors ; Kinetics ; Life Sciences ; Molecular Structure ; Neurobiology ; Organic chemistry ; Original Article ; Proteomics ; Pseudomonas aeruginosa ; Stereoisomerism ; Structure-Activity Relationship ; Substrate inhibition</subject><ispartof>Amino acids, 2012-04, Vol.42 (4), p.1339-1348</ispartof><rights>Springer-Verlag 2011</rights><rights>Springer-Verlag 2012</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c438t-2f58d732c5a2fa0d34d63073f2b5eec2de5a5b03bf0a21af7e11bf841e047623</citedby><cites>FETCH-LOGICAL-c438t-2f58d732c5a2fa0d34d63073f2b5eec2de5a5b03bf0a21af7e11bf841e047623</cites><orcidid>0000-0003-4503-3554 ; 0000-0002-6189-9860</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00726-010-0829-3$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00726-010-0829-3$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>230,314,780,784,885,27924,27925,41488,42557,51319</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21279396$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00616942$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Moussa, Amer</creatorcontrib><creatorcontrib>Meffre, Patrick</creatorcontrib><creatorcontrib>Martinez, Jean</creatorcontrib><creatorcontrib>Rolland, Valérie</creatorcontrib><title>Chemoenzymatic routes to enantiomerically pure 2-azatyrosine and 2-, 3- and 4-pyridylalanine derivatives</title><title>Amino acids</title><addtitle>Amino Acids</addtitle><addtitle>Amino Acids</addtitle><description>Enantiomerically pure 2-, 3- or 4-pyridylalanine (pya) and 2-azatyrosine (azatyr) are known to present various biological activities. After incorporation into appropriate peptide sequences, these heterocyclic non natural α-amino acids could behave as new substrates or inhibitors of elastase from
Pseudomonas aeruginosa
. This enzyme is known to be involved in nosocomial infections and infections related to the cystic fibrosis disease. New efficient chemoenzymatic preparations of those compounds using α-chymotrypsin (α-CT) are presented.</description><subject>Alanine - analogs & derivatives</subject><subject>Alanine - chemical synthesis</subject><subject>Alanine - chemistry</subject><subject>Alanine - pharmacology</subject><subject>Amino acids</subject><subject>Analytical Chemistry</subject><subject>Biochemical Engineering</subject><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Catalysis</subject><subject>Chemical Sciences</subject><subject>Chymotrypsin - antagonists & inhibitors</subject><subject>Cystic fibrosis</subject><subject>Derivatives</subject><subject>Elastase</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Enzymes</subject><subject>Inhibitors</subject><subject>Kinetics</subject><subject>Life Sciences</subject><subject>Molecular Structure</subject><subject>Neurobiology</subject><subject>Organic chemistry</subject><subject>Original Article</subject><subject>Proteomics</subject><subject>Pseudomonas aeruginosa</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><subject>Substrate inhibition</subject><issn>0939-4451</issn><issn>1438-2199</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNp9kU9v1DAQxS1ERZfCB-CCInEAJFxmbMeOj9UKKNJKvfRuOcmETZU_i52slH56vE2pEBJcbGveb57Hfoy9QbhEAPM5pkVoDggcCmG5fMY2qGTBBVr7nG3ASsuVyvGcvYzxDgBFgfoFOxcoTNL0hu23e-pHGu6X3k9tlYVxnihm05jR4IepHXsKbeW7bskOc6BMcH_vpyWMsR0o80OdKp8yyR-Oih-W0NZL5zs_nPQ6NR-T75HiK3bW-C7S68f9gt1-_XK7vea7m2_ft1c7XqXBJy6avKiNFFXuReOhlqrWEoxsRJkTVaKm3OclyLIBL9A3hhDLplBIoIwW8oJ9XG33vnOH0PY-LG70rbu-2rlTDUCjtkocMbHvV_YQxp8zxcn1bayoS8PTOEdnhS5MIbVJ5If_kghotTLGQELf_YXejXMY0pMTZbXWUFiVKFypKv1kDNQ8zYrgTtm6NVuXsnWnbJ1MPW8fneeyp_qp43eYCRArEJM0_KDw59X_cv0FdQatWg</recordid><startdate>20120401</startdate><enddate>20120401</enddate><creator>Moussa, Amer</creator><creator>Meffre, Patrick</creator><creator>Martinez, Jean</creator><creator>Rolland, Valérie</creator><general>Springer Vienna</general><general>Springer Nature B.V</general><general>Springer Verlag</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7TK</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8AO</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>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M7P</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0003-4503-3554</orcidid><orcidid>https://orcid.org/0000-0002-6189-9860</orcidid></search><sort><creationdate>20120401</creationdate><title>Chemoenzymatic routes to enantiomerically pure 2-azatyrosine and 2-, 3- and 4-pyridylalanine derivatives</title><author>Moussa, Amer ; Meffre, Patrick ; Martinez, Jean ; Rolland, Valérie</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c438t-2f58d732c5a2fa0d34d63073f2b5eec2de5a5b03bf0a21af7e11bf841e047623</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Alanine - analogs & derivatives</topic><topic>Alanine - chemical synthesis</topic><topic>Alanine - chemistry</topic><topic>Alanine - pharmacology</topic><topic>Amino acids</topic><topic>Analytical Chemistry</topic><topic>Biochemical Engineering</topic><topic>Biochemistry</topic><topic>Biomedical and Life Sciences</topic><topic>Catalysis</topic><topic>Chemical Sciences</topic><topic>Chymotrypsin - antagonists & inhibitors</topic><topic>Cystic fibrosis</topic><topic>Derivatives</topic><topic>Elastase</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Enzymes</topic><topic>Inhibitors</topic><topic>Kinetics</topic><topic>Life Sciences</topic><topic>Molecular Structure</topic><topic>Neurobiology</topic><topic>Organic chemistry</topic><topic>Original Article</topic><topic>Proteomics</topic><topic>Pseudomonas aeruginosa</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><topic>Substrate inhibition</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Moussa, Amer</creatorcontrib><creatorcontrib>Meffre, Patrick</creatorcontrib><creatorcontrib>Martinez, Jean</creatorcontrib><creatorcontrib>Rolland, Valérie</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Neurosciences Abstracts</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</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 Edition)</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>Natural Science Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</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>Materials Science Database</collection><collection>ProQuest Biological Science Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Biological Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - 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After incorporation into appropriate peptide sequences, these heterocyclic non natural α-amino acids could behave as new substrates or inhibitors of elastase from
Pseudomonas aeruginosa
. This enzyme is known to be involved in nosocomial infections and infections related to the cystic fibrosis disease. New efficient chemoenzymatic preparations of those compounds using α-chymotrypsin (α-CT) are presented.</abstract><cop>Vienna</cop><pub>Springer Vienna</pub><pmid>21279396</pmid><doi>10.1007/s00726-010-0829-3</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0003-4503-3554</orcidid><orcidid>https://orcid.org/0000-0002-6189-9860</orcidid><oa>free_for_read</oa></addata></record> |
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| ispartof | Amino acids, 2012-04, Vol.42 (4), p.1339-1348 |
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| subjects | Alanine - analogs & derivatives Alanine - chemical synthesis Alanine - chemistry Alanine - pharmacology Amino acids Analytical Chemistry Biochemical Engineering Biochemistry Biomedical and Life Sciences Catalysis Chemical Sciences Chymotrypsin - antagonists & inhibitors Cystic fibrosis Derivatives Elastase Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Enzymes Inhibitors Kinetics Life Sciences Molecular Structure Neurobiology Organic chemistry Original Article Proteomics Pseudomonas aeruginosa Stereoisomerism Structure-Activity Relationship Substrate inhibition |
| title | Chemoenzymatic routes to enantiomerically pure 2-azatyrosine and 2-, 3- and 4-pyridylalanine derivatives |
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