In Vivo Expression of Genetic Information from Phosphoramidate–DNA
Chemically modified genes and genomes with customized properties will become a valuable tool in numerous fields, including synthetic biology, biotechnology, and medicine. These genetic materials are meant to store and exchange information with DNA and RNA while tuning their functionality. Herein, we...
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| Veröffentlicht in: | Chembiochem : a European journal of chemical biology 2020-01, Vol.21 (1-2), p.272-278 |
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| container_title | Chembiochem : a European journal of chemical biology |
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| creator | Nguyen, Hoai Abramov, Mikhail Eremeeva, Elena Herdewijn, Piet |
| description | Chemically modified genes and genomes with customized properties will become a valuable tool in numerous fields, including synthetic biology, biotechnology, and medicine. These genetic materials are meant to store and exchange information with DNA and RNA while tuning their functionality. Herein, we outline the development of an alternative genetic system carrying phosphoramidate linkages that successfully propagates genetic information in bacteria and at the same time is labile to acidic conditions. The P3′→N5′ phosphoramidate‐containing DNA (PN‐DNA) was enzymatically synthesized by using 5′‐amino‐2′,5′‐deoxycytidine 5′‐N‐triphosphates (NH‐dCTPs) as substrates for DNA polymerases and employed to encode antibiotic resistance in Escherichia coli. The resulting PN‐DNA can be efficiently destroyed by mild acidic conditions, whereas an unmodified counterpart remains intact. A cloning strategy was proposed for assembling modified fragments into a genome. This method can be of interest to scientists working in the field of orthogonal nucleic acid genes and genomes.
The path of more resistance: Genetic information can be stored in a chemically altered DNA carrying several acid‐labile phosphoramidate linkages. The modified gene was assembled from complementary single‐stranded DNA fragments and successfully induced resistance to the antibiotic trimethoprim in bacteria. |
| doi_str_mv | 10.1002/cbic.201900712 |
| format | Article |
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The path of more resistance: Genetic information can be stored in a chemically altered DNA carrying several acid‐labile phosphoramidate linkages. The modified gene was assembled from complementary single‐stranded DNA fragments and successfully induced resistance to the antibiotic trimethoprim in bacteria.</description><identifier>ISSN: 1439-4227</identifier><identifier>EISSN: 1439-7633</identifier><identifier>DOI: 10.1002/cbic.201900712</identifier><identifier>PMID: 31868979</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Amides - chemistry ; Antibiotic resistance ; Antibiotics ; Biotechnology ; chemically modified organisms ; Cloning ; Deoxyribonucleic acid ; DNA ; DNA - chemistry ; DNA - genetics ; DNA-directed DNA polymerase ; E coli ; Gene expression ; Gene Expression Profiling ; Genes ; Genomes ; Hydrogen-Ion Concentration ; modified genes ; Nucleic acids ; Oligonucleotides - chemistry ; Organic chemistry ; phosphoramidate bond ; Phosphoric Acids - chemistry ; Polymerase Chain Reaction ; Ribonucleic acid ; RNA ; Substrates ; synthetic biology</subject><ispartof>Chembiochem : a European journal of chemical biology, 2020-01, Vol.21 (1-2), p.272-278</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5162-e32570971b1142c78400bd2d464faf39e632882b307568f7fe2ccbf036546fc63</citedby><cites>FETCH-LOGICAL-c5162-e32570971b1142c78400bd2d464faf39e632882b307568f7fe2ccbf036546fc63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcbic.201900712$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbic.201900712$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31868979$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nguyen, Hoai</creatorcontrib><creatorcontrib>Abramov, Mikhail</creatorcontrib><creatorcontrib>Eremeeva, Elena</creatorcontrib><creatorcontrib>Herdewijn, Piet</creatorcontrib><title>In Vivo Expression of Genetic Information from Phosphoramidate–DNA</title><title>Chembiochem : a European journal of chemical biology</title><addtitle>Chembiochem</addtitle><description>Chemically modified genes and genomes with customized properties will become a valuable tool in numerous fields, including synthetic biology, biotechnology, and medicine. These genetic materials are meant to store and exchange information with DNA and RNA while tuning their functionality. Herein, we outline the development of an alternative genetic system carrying phosphoramidate linkages that successfully propagates genetic information in bacteria and at the same time is labile to acidic conditions. The P3′→N5′ phosphoramidate‐containing DNA (PN‐DNA) was enzymatically synthesized by using 5′‐amino‐2′,5′‐deoxycytidine 5′‐N‐triphosphates (NH‐dCTPs) as substrates for DNA polymerases and employed to encode antibiotic resistance in Escherichia coli. The resulting PN‐DNA can be efficiently destroyed by mild acidic conditions, whereas an unmodified counterpart remains intact. A cloning strategy was proposed for assembling modified fragments into a genome. This method can be of interest to scientists working in the field of orthogonal nucleic acid genes and genomes.
The path of more resistance: Genetic information can be stored in a chemically altered DNA carrying several acid‐labile phosphoramidate linkages. The modified gene was assembled from complementary single‐stranded DNA fragments and successfully induced resistance to the antibiotic trimethoprim in bacteria.</description><subject>Amides - chemistry</subject><subject>Antibiotic resistance</subject><subject>Antibiotics</subject><subject>Biotechnology</subject><subject>chemically modified organisms</subject><subject>Cloning</subject><subject>Deoxyribonucleic acid</subject><subject>DNA</subject><subject>DNA - chemistry</subject><subject>DNA - genetics</subject><subject>DNA-directed DNA polymerase</subject><subject>E coli</subject><subject>Gene expression</subject><subject>Gene Expression Profiling</subject><subject>Genes</subject><subject>Genomes</subject><subject>Hydrogen-Ion Concentration</subject><subject>modified genes</subject><subject>Nucleic acids</subject><subject>Oligonucleotides - chemistry</subject><subject>Organic chemistry</subject><subject>phosphoramidate bond</subject><subject>Phosphoric Acids - chemistry</subject><subject>Polymerase Chain Reaction</subject><subject>Ribonucleic acid</subject><subject>RNA</subject><subject>Substrates</subject><subject>synthetic biology</subject><issn>1439-4227</issn><issn>1439-7633</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkL9OwzAQhy0EoqWwMqJILCwt5z-x47G0pUSqgAFYo8Sx1VRNXOwE6MY78IY8CalaQGJhutPpu9-dPoROMQwwALlUWaEGBLAEEJjsoS5mVPYFp3R_1zNCRAcdeb8AAMkpPkQdiiMeSSG7aBxXwVPxYoPJ28pp7wtbBdYEU13pulBBXBnryrTejI2zZXA_t341ty4tizyt9ef7x_h2eIwOTLr0-mRXe-jxevIwuunP7qbxaDjrqxBz0teUhAKkwBnGjCgRMYAsJznjzKSGSs0piSKSURAhj4wwmiiVGaA8ZNwoTnvoYpu7cva50b5OysIrvVymlbaNTwilAByHHLfo-R90YRtXtd-1FGvPR5JtqMGWUs5677RJVq4oU7dOMCQbv8nGb_Ljt10428U2WanzH_xbaAvILfBaLPX6n7hkdBWPfsO_ALhYhU4</recordid><startdate>20200115</startdate><enddate>20200115</enddate><creator>Nguyen, Hoai</creator><creator>Abramov, Mikhail</creator><creator>Eremeeva, Elena</creator><creator>Herdewijn, Piet</creator><general>Wiley Subscription Services, Inc</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>7QL</scope><scope>7QO</scope><scope>7TM</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>K9.</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20200115</creationdate><title>In Vivo Expression of Genetic Information from Phosphoramidate–DNA</title><author>Nguyen, Hoai ; Abramov, Mikhail ; Eremeeva, Elena ; Herdewijn, Piet</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5162-e32570971b1142c78400bd2d464faf39e632882b307568f7fe2ccbf036546fc63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Amides - chemistry</topic><topic>Antibiotic resistance</topic><topic>Antibiotics</topic><topic>Biotechnology</topic><topic>chemically modified organisms</topic><topic>Cloning</topic><topic>Deoxyribonucleic acid</topic><topic>DNA</topic><topic>DNA - chemistry</topic><topic>DNA - genetics</topic><topic>DNA-directed DNA polymerase</topic><topic>E coli</topic><topic>Gene expression</topic><topic>Gene Expression Profiling</topic><topic>Genes</topic><topic>Genomes</topic><topic>Hydrogen-Ion Concentration</topic><topic>modified genes</topic><topic>Nucleic acids</topic><topic>Oligonucleotides - chemistry</topic><topic>Organic chemistry</topic><topic>phosphoramidate bond</topic><topic>Phosphoric Acids - chemistry</topic><topic>Polymerase Chain Reaction</topic><topic>Ribonucleic acid</topic><topic>RNA</topic><topic>Substrates</topic><topic>synthetic biology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nguyen, Hoai</creatorcontrib><creatorcontrib>Abramov, Mikhail</creatorcontrib><creatorcontrib>Eremeeva, Elena</creatorcontrib><creatorcontrib>Herdewijn, Piet</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chembiochem : a European journal of chemical biology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nguyen, Hoai</au><au>Abramov, Mikhail</au><au>Eremeeva, Elena</au><au>Herdewijn, Piet</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>In Vivo Expression of Genetic Information from Phosphoramidate–DNA</atitle><jtitle>Chembiochem : a European journal of chemical biology</jtitle><addtitle>Chembiochem</addtitle><date>2020-01-15</date><risdate>2020</risdate><volume>21</volume><issue>1-2</issue><spage>272</spage><epage>278</epage><pages>272-278</pages><issn>1439-4227</issn><eissn>1439-7633</eissn><abstract>Chemically modified genes and genomes with customized properties will become a valuable tool in numerous fields, including synthetic biology, biotechnology, and medicine. These genetic materials are meant to store and exchange information with DNA and RNA while tuning their functionality. Herein, we outline the development of an alternative genetic system carrying phosphoramidate linkages that successfully propagates genetic information in bacteria and at the same time is labile to acidic conditions. The P3′→N5′ phosphoramidate‐containing DNA (PN‐DNA) was enzymatically synthesized by using 5′‐amino‐2′,5′‐deoxycytidine 5′‐N‐triphosphates (NH‐dCTPs) as substrates for DNA polymerases and employed to encode antibiotic resistance in Escherichia coli. The resulting PN‐DNA can be efficiently destroyed by mild acidic conditions, whereas an unmodified counterpart remains intact. A cloning strategy was proposed for assembling modified fragments into a genome. This method can be of interest to scientists working in the field of orthogonal nucleic acid genes and genomes.
The path of more resistance: Genetic information can be stored in a chemically altered DNA carrying several acid‐labile phosphoramidate linkages. The modified gene was assembled from complementary single‐stranded DNA fragments and successfully induced resistance to the antibiotic trimethoprim in bacteria.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>31868979</pmid><doi>10.1002/cbic.201900712</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Amides - chemistry Antibiotic resistance Antibiotics Biotechnology chemically modified organisms Cloning Deoxyribonucleic acid DNA DNA - chemistry DNA - genetics DNA-directed DNA polymerase E coli Gene expression Gene Expression Profiling Genes Genomes Hydrogen-Ion Concentration modified genes Nucleic acids Oligonucleotides - chemistry Organic chemistry phosphoramidate bond Phosphoric Acids - chemistry Polymerase Chain Reaction Ribonucleic acid RNA Substrates synthetic biology |
| title | In Vivo Expression of Genetic Information from Phosphoramidate–DNA |
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