Synthesis and polymerase activity of a fluorescent cytidine TNA triphosphate analogue
Threose nucleic acid (TNA) is an artificial genetic polymer capable of undergoing Darwinian evolution to produce aptamers with affinity to specific targets. This property, coupled with a backbone structure that is refractory to nuclease digestion, makes TNA an attractive biopolymer system for diagno...
Saved in:
Published in | Nucleic acids research Vol. 45; no. 10; pp. 5629 - 5638 |
---|---|
Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
England
Oxford University Press
02.06.2017
|
Subjects | |
Online Access | Get full text |
Cover
Loading…
Abstract | Threose nucleic acid (TNA) is an artificial genetic polymer capable of undergoing Darwinian evolution to produce aptamers with affinity to specific targets. This property, coupled with a backbone structure that is refractory to nuclease digestion, makes TNA an attractive biopolymer system for diagnostic and therapeutic applications. Expanding the chemical diversity of TNA beyond the natural bases would enable the development of functional TNA molecules with enhanced physiochemical properties. Here, we describe the synthesis and polymerase activity of a fluorescent cytidine TNA triphosphate analogue (1,3-diaza-2-oxo-phenothiazine, tCfTP) that maintains Watson-Crick base pairing with guanine. Polymerase-mediated primer-extension assays reveal that tCfTP is efficiently added to the growing end of a TNA primer. Detailed kinetic assays indicate that tCfTP and tCTP have comparable rates for the first nucleotide incorporation step (kobs1). However, addition of the second nucleotide (kobs2) is 700-fold faster for tCfTP than tCTP due the increased effects of base stacking. Last, we found that TNA replication using tCfTP in place of tCTP exhibits 98.4% overall fidelity for the combined process of TNA transcription and reverse transcription. Together, these results expand the chemical diversity of enzymatically generated TNA molecules to include a hydrophobic base analogue with strong fluorescent properties that is compatible with in vitro selection. |
---|---|
AbstractList | Threose nucleic acid (TNA) is an artificial genetic polymer capable of undergoing Darwinian evolution to produce aptamers with affinity to specific targets. This property, coupled with a backbone structure that is refractory to nuclease digestion, makes TNA an attractive biopolymer system for diagnostic and therapeutic applications. Expanding the chemical diversity of TNA beyond the natural bases would enable the development of functional TNA molecules with enhanced physiochemical properties. Here, we describe the synthesis and polymerase activity of a fluorescent cytidine TNA triphosphate analogue (1,3-diaza-2-oxo-phenothiazine, tCfTP) that maintains Watson-Crick base pairing with guanine. Polymerase-mediated primer-extension assays reveal that tCfTP is efficiently added to the growing end of a TNA primer. Detailed kinetic assays indicate that tCfTP and tCTP have comparable rates for the first nucleotide incorporation step (kobs1). However, addition of the second nucleotide (kobs2) is 700-fold faster for tCfTP than tCTP due the increased effects of base stacking. Last, we found that TNA replication using tCfTP in place of tCTP exhibits 98.4% overall fidelity for the combined process of TNA transcription and reverse transcription. Together, these results expand the chemical diversity of enzymatically generated TNA molecules to include a hydrophobic base analogue with strong fluorescent properties that is compatible with in vitro selection. Threose nucleic acid (TNA) is an artificial genetic polymer capable of undergoing Darwinian evolution to produce aptamers with affinity to specific targets. This property, coupled with a backbone structure that is refractory to nuclease digestion, makes TNA an attractive biopolymer system for diagnostic and therapeutic applications. Expanding the chemical diversity of TNA beyond the natural bases would enable the development of functional TNA molecules with enhanced physiochemical properties. Here, we describe the synthesis and polymerase activity of a fluorescent cytidine TNA triphosphate analogue (1,3-diaza-2-oxo-phenothiazine, tC f TP) that maintains Watson-Crick base pairing with guanine. Polymerase-mediated primer-extension assays reveal that tC f TP is efficiently added to the growing end of a TNA primer. Detailed kinetic assays indicate that tC f TP and tCTP have comparable rates for the first nucleotide incorporation step ( k obs1 ). However, addition of the second nucleotide ( k obs2 ) is 700-fold faster for tC f TP than tCTP due the increased effects of base stacking. Last, we found that TNA replication using tC f TP in place of tCTP exhibits 98.4% overall fidelity for the combined process of TNA transcription and reverse transcription. Together, these results expand the chemical diversity of enzymatically generated TNA molecules to include a hydrophobic base analogue with strong fluorescent properties that is compatible with in vitro selection. |
Author | Kardouh, Miramar Jimenez, Randi M Wang, Yajun Chaput, John C Shi, Changhua Mei, Hui |
AuthorAffiliation | Department of Pharmaceutical Sciences, University of California, Irvine, CA 92697-3958, USA |
AuthorAffiliation_xml | – name: Department of Pharmaceutical Sciences, University of California, Irvine, CA 92697-3958, USA |
Author_xml | – sequence: 1 givenname: Hui surname: Mei fullname: Mei, Hui organization: Department of Pharmaceutical Sciences, University of California, Irvine, CA 92697-3958, USA – sequence: 2 givenname: Changhua surname: Shi fullname: Shi, Changhua organization: Department of Pharmaceutical Sciences, University of California, Irvine, CA 92697-3958, USA – sequence: 3 givenname: Randi M surname: Jimenez fullname: Jimenez, Randi M organization: Department of Pharmaceutical Sciences, University of California, Irvine, CA 92697-3958, USA – sequence: 4 givenname: Yajun surname: Wang fullname: Wang, Yajun organization: Department of Pharmaceutical Sciences, University of California, Irvine, CA 92697-3958, USA – sequence: 5 givenname: Miramar surname: Kardouh fullname: Kardouh, Miramar organization: Department of Pharmaceutical Sciences, University of California, Irvine, CA 92697-3958, USA – sequence: 6 givenname: John C surname: Chaput fullname: Chaput, John C organization: Department of Pharmaceutical Sciences, University of California, Irvine, CA 92697-3958, USA |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28472363$$D View this record in MEDLINE/PubMed |
BookMark | eNpVkU1LxDAQhoMoun5c_AGSowjVpEm66UWQxS8QPbieQ9pOdqPdpCap2H9vZVfR0wzMM-98vPto23kHCB1Tck5JyS6cDheLt09WyC00oazIM14W-TaaEEZERgmXe2g_xldCKKeC76K9XPJpzgo2QS_Pg0tLiDZi7Rrc-XZYQdARsK6T_bBpwN5gjU3b-wCxBpdwPSTbWAd4_niFU7Dd0sduqdPY43TrFz0coh2j2whHm3iAXm6u57O77OHp9n529ZDVbCpTVolCGihqIYqSa1ZWY9rwkhNdM1NJKpoGQE4l18KUAnJWidyMFJdNVRum2QG6XOt2fbWC5nu7oFvVBbvSYVBeW_W_4uxSLfyHEpyXQopR4HQjEPx7DzGplR2PbFvtwPdRUVkWhOc5YyN6tkbr4GMMYH7HUKK-fVCjD2rtwwif_F3sF_15PPsCbTaJiQ |
CitedBy_id | crossref_primary_10_1016_j_ymeth_2019_03_018 crossref_primary_10_1101_cshperspect_a032490 crossref_primary_10_1038_s41570_017_0076 crossref_primary_10_1038_s41598_020_64541_z crossref_primary_10_1261_rna_077008_120 crossref_primary_10_1016_j_addr_2018_04_007 crossref_primary_10_1093_nar_gkad502 crossref_primary_10_3390_bios12020093 crossref_primary_10_1186_s12915_020_00803_6 crossref_primary_10_3390_genes10010017 crossref_primary_10_1016_j_bmcl_2021_128242 crossref_primary_10_1007_s40242_021_2186_7 crossref_primary_10_1039_D0CB00078G crossref_primary_10_1007_s40242_022_2186_7 crossref_primary_10_1002_bip_23388 crossref_primary_10_1002_chem_201801976 crossref_primary_10_1093_nar_gkz513 crossref_primary_10_1039_C7CC09130C crossref_primary_10_1039_D0CS01430C crossref_primary_10_1039_C9OB01515A crossref_primary_10_1016_j_bioorg_2023_107049 crossref_primary_10_1021_acs_accounts_0c00886 crossref_primary_10_1021_jacs_7b13031 crossref_primary_10_1038_s42003_019_0458_7 |
ContentType | Journal Article |
Copyright | The Author(s) 2017. Published by Oxford University Press on behalf of Nucleic Acids Research. The Author(s) 2017. Published by Oxford University Press on behalf of Nucleic Acids Research. 2017 |
Copyright_xml | – notice: The Author(s) 2017. Published by Oxford University Press on behalf of Nucleic Acids Research. – notice: The Author(s) 2017. Published by Oxford University Press on behalf of Nucleic Acids Research. 2017 |
DBID | CGR CUY CVF ECM EIF NPM AAYXX CITATION 7X8 5PM |
DOI | 10.1093/nar/gkx368 |
DatabaseName | Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed CrossRef MEDLINE - Academic PubMed Central (Full Participant titles) |
DatabaseTitle | MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) CrossRef MEDLINE - Academic |
DatabaseTitleList | MEDLINE - Academic MEDLINE |
Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: EIF name: MEDLINE url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/medline/basic-search sourceTypes: Index Database |
DeliveryMethod | fulltext_linktorsrc |
Discipline | Anatomy & Physiology Chemistry |
EISSN | 1362-4962 |
EndPage | 5638 |
ExternalDocumentID | 10_1093_nar_gkx368 28472363 |
Genre | Journal Article |
GroupedDBID | --- -DZ -~X .I3 0R~ 123 18M 1TH 29N 2WC 4.4 482 53G 5VS 5WA 70E 85S A8Z AAFWJ AAHBH AAMVS AAOGV AAPPN AAPXW AAUQX AAVAP ABPTD ABQLI ABXVV ACGFO ACGFS ACIWK ACNCT ACPRK ADBBV ADHZD AEGXH AENEX AENZO AFFNX AFRAH AFULF AHMBA AIAGR ALMA_UNASSIGNED_HOLDINGS ALUQC AOIJS BAWUL BAYMD BCNDV BTTYL CAG CGR CIDKT CS3 CUY CVF CZ4 DIK DU5 D~K E3Z EBD EBS ECM EIF EJD EMOBN ESTFP F5P GROUPED_DOAJ GX1 H13 HH5 HYE HZ~ IH2 KAQDR KQ8 KSI M49 M~E NPM NU- OAWHX OBC OBS OEB OES OJQWA P2P PEELM PQQKQ R44 RD5 RNS ROL ROX ROZ RPM RXO SV3 TN5 TOX TR2 WG7 WOQ X7H XSB YSK ZKX ~91 ~D7 ~KM AAYXX AFPKN CITATION 7X8 5PM |
ID | FETCH-LOGICAL-c378t-b568fe6c55694a39b6c5d4940ac3fb815ddee8784a5f95e23b52f9b648dbcf3a3 |
IEDL.DBID | RPM |
ISSN | 0305-1048 |
IngestDate | Tue Sep 17 21:26:08 EDT 2024 Sat Aug 17 03:40:34 EDT 2024 Fri Aug 23 03:39:05 EDT 2024 Wed Oct 16 00:00:26 EDT 2024 |
IsDoiOpenAccess | true |
IsOpenAccess | true |
IsPeerReviewed | true |
IsScholarly | true |
Issue | 10 |
Language | English |
License | The Author(s) 2017. Published by Oxford University Press on behalf of Nucleic Acids Research. This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by-nc/4.0/), which permits non-commercial re-use, distribution, and reproduction in any medium, provided the original work is properly cited. For commercial re-use, please contact journals.permissions@oup.com |
LinkModel | DirectLink |
MergedId | FETCHMERGED-LOGICAL-c378t-b568fe6c55694a39b6c5d4940ac3fb815ddee8784a5f95e23b52f9b648dbcf3a3 |
Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
OpenAccessLink | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5449585/ |
PMID | 28472363 |
PQID | 1896042233 |
PQPubID | 23479 |
PageCount | 10 |
ParticipantIDs | pubmedcentral_primary_oai_pubmedcentral_nih_gov_5449585 proquest_miscellaneous_1896042233 crossref_primary_10_1093_nar_gkx368 pubmed_primary_28472363 |
PublicationCentury | 2000 |
PublicationDate | 2017-06-02 |
PublicationDateYYYYMMDD | 2017-06-02 |
PublicationDate_xml | – month: 06 year: 2017 text: 2017-06-02 day: 02 |
PublicationDecade | 2010 |
PublicationPlace | England |
PublicationPlace_xml | – name: England |
PublicationTitle | Nucleic acids research |
PublicationTitleAlternate | Nucleic Acids Res |
PublicationYear | 2017 |
Publisher | Oxford University Press |
Publisher_xml | – name: Oxford University Press |
References | 16157867 - Nucleic Acids Res. 2005 Sep 12;33(16):5219-25 8430089 - Proc Natl Acad Sci U S A. 1993 Feb 1;90(3):804-8 27422338 - Bioorg Med Chem Lett. 2016 Aug 15;26(16):3958-62 21477595 - J Mol Biol. 2011 Jun 3;409(2):89-100 11082060 - Science. 2000 Nov 17;290(5495):1347-51 26860781 - ACS Chem Biol. 2016 May 20;11(5):1210-9 15898792 - J Am Chem Soc. 2005 May 25;127(20):7427-34 14576309 - Nucleic Acids Res. 2003 Nov 1;31(21):6221-6 25684598 - Chemistry. 2015 Mar 23;21(13):5009-22 15740086 - J Am Chem Soc. 2005 Mar 9;127(9):2802-3 12537469 - J Am Chem Soc. 2003 Jan 29;125(4):856-7 20201573 - J Am Chem Soc. 2010 Mar 31;132(12):4141-51 26304162 - Angew Chem Int Ed Engl. 2015 Oct 5;54(41):11930-44 23177191 - Chem Biol. 2012 Nov 21;19(11):1360-71 27044725 - Nat Commun. 2016 Apr 05;7:11235 17406622 - Nat Protoc. 2007;2(3):615-23 12889939 - J Am Chem Soc. 2003 Aug 6;125(31):9274-5 27383648 - Chembiochem. 2016 Oct 4;17 (19):1804-1808 26895480 - J Org Chem. 2016 Mar 18;81(6):2302-7 20067253 - Anal Chem. 2010 Feb 1;82(3):1082-9 19401439 - Nucleic Acids Res. 2009 Jul;37(12):3924-33 27246616 - Bioorg Med Chem Lett. 2016 Jul 15;26(14):3271-3 15452275 - Nucleic Acids Res. 2004 Sep 27;32(17):5087-95 22517858 - Science. 2012 Apr 20;336(6079):341-4 27080186 - Bioorg Med Chem Lett. 2016 May 15;26(10):2418-21 11749283 - Chem Rev. 2000 Jun 14;100(6):2047-60 22354431 - Nat Chem. 2012 Jan 10;4(3):183-7 17828568 - J Mol Evol. 2007 Sep;65(3):289-95 27347671 - Chembiochem. 2016 Sep 15;17 (18):1705-8 26389865 - Molecules. 2015 Sep 14;20(9):16643-71 19580325 - Biochemistry. 2009 Aug 11;48(31):7547-55 18928287 - J Am Chem Soc. 2008 Nov 12;130(45):15105-15 17915941 - Biochemistry. 2007 Oct 30;46(43):12289-97 24409991 - J Am Chem Soc. 2014 Feb 5;136(5):2033-9 Kempeneers ( key 20180801083947_B10) 2003; 31 Larsen ( key 20180801083947_B16) 2016; 7 Culbertson ( key 20180801083947_B7) 2016; 26 Malyshev ( key 20180801083947_B34) 2015; 54 Anosova ( key 20180801083947_B5) 2016; 17 Stengel ( key 20180801083947_B24) 2007; 46 Chaput ( key 20180801083947_B8) 2003; 125 Dunn ( key 20180801083947_B17) 2016; 11 Diafa ( key 20180801083947_B36) 2015; 20 Sandin ( key 20180801083947_B23) 2009; 37 Schöning ( key 20180801083947_B2) 2000; 290 Yang ( key 20180801083947_B4) 2007; 65 Sau ( key 20180801083947_B30) 2016; 26 Chaput ( key 20180801083947_B9) 2003; 125 Dunn ( key 20180801083947_B33) 2016; 17 Horhota ( key 20180801083947_B11) 2005; 127 Stengel ( key 20180801083947_B26) 2010; 82 Ebert ( key 20180801083947_B6) 2008; 130 Chen ( key 20180801083947_B32) 2016; 26 Schöning ( key 20180801083947_B3) 2002; 85 Engman ( key 20180801083947_B21) 2004; 32 Walsh ( key 20180801083947_B25) 2011; 409 Sau ( key 20180801083947_B27) 2016; 81 Bande ( key 20180801083947_B37) 2015; 21 Chaput ( key 20180801083947_B1) 2012; 19 Sandin ( key 20180801083947_B20) 2007; 2 Burgess ( key 20180801083947_B31) 2000; 100 Skelly ( key 20180801083947_B18) 1993; 90 Stengel ( key 20180801083947_B22) 2009; 48 Bain ( key 20180801083947_B28) 2014; 136 Ichida ( key 20180801083947_B13) 2005; 127 Yu ( key 20180801083947_B14) 2012; 4 Lin ( key 20180801083947_B19) 1995; 117 Wilhelmsson ( key 20180801083947_B29) 2003; 107 Vaught ( key 20180801083947_B35) 2010; 132 Ichida ( key 20180801083947_B12) 2005; 33 Pinheiro ( key 20180801083947_B15) 2012; 336 |
References_xml | – volume: 48 start-page: 7547 year: 2009 ident: key 20180801083947_B22 article-title: Ambivalent incorporation of the fluorescent cytosine analogues tC and tCo by human DNA polymerase a and Klenow fragment publication-title: Biochemistry contributor: fullname: Stengel – volume: 409 start-page: 89 year: 2011 ident: key 20180801083947_B25 article-title: Discrimination against the cytosine analog tC by Escherichia coli DNA polymerase IV DinB publication-title: J Mol Biol contributor: fullname: Walsh – volume: 130 start-page: 15105 year: 2008 ident: key 20180801083947_B6 article-title: The structure of a TNA-TNA complex in solution: NMR study of the octamer duplex derived from a-(L)-threofuranosyl-(3΄-2΄)-CGAATTCG publication-title: J. Am. Chem. Soc. contributor: fullname: Ebert – volume: 26 start-page: 3958 year: 2016 ident: key 20180801083947_B32 article-title: Synthesis and polymerase incorporation of b,g-modified a-L-threofuranosyl thymine triphosphate mimics publication-title: Bioorg. Med. Chem. Lett. contributor: fullname: Chen – volume: 107 start-page: 9094 year: 2003 ident: key 20180801083947_B29 article-title: Photophysical characterization of fluorescent DNA base analogue, tC publication-title: J. Phys. Chem. B contributor: fullname: Wilhelmsson – volume: 26 start-page: 2418 year: 2016 ident: key 20180801083947_B7 article-title: Evaluating TNA stability under simulated physiological conditions publication-title: Bioorg. Med. Chem. Lett. contributor: fullname: Culbertson – volume: 17 start-page: 1705 year: 2016 ident: key 20180801083947_B5 article-title: Structural insights into conformational differences betweeen DNA/TNA and RNA/TNA chimeric duplexes publication-title: ChemBioChem contributor: fullname: Anosova – volume: 32 start-page: 5087 year: 2004 ident: key 20180801083947_B21 article-title: DNA adopts normal B-form upon incorporation of highly fluorescent DNA base analogue tC: NMR structure and UV-vis spectroscopy characterization publication-title: Nucleic Acids Res contributor: fullname: Engman – volume: 125 start-page: 856 year: 2003 ident: key 20180801083947_B8 article-title: DNA polymerase-mediated DNA synthesis on a TNA template publication-title: J. Am. Chem. Soc. contributor: fullname: Chaput – volume: 19 start-page: 1360 year: 2012 ident: key 20180801083947_B1 article-title: The emerging world of synthetic genetics publication-title: Chem. Biol. contributor: fullname: Chaput – volume: 46 start-page: 12289 year: 2007 ident: key 20180801083947_B24 article-title: Conformational dynamics of DNA polymerase probed with a novel fluorescent DNA base analogue publication-title: Biochemistry contributor: fullname: Stengel – volume: 132 start-page: 4141 year: 2010 ident: key 20180801083947_B35 article-title: Expanding the chemistry of DNA for in vitro selection publication-title: J. Am. Chem. Soc. contributor: fullname: Vaught – volume: 17 start-page: 1804 year: 2016 ident: key 20180801083947_B33 article-title: Reverse transcription of threose nucleic acid by a naturally occurring DNA polymerase publication-title: ChemBioChem contributor: fullname: Dunn – volume: 20 start-page: 16643 year: 2015 ident: key 20180801083947_B36 article-title: Generation of aptamers with an expanded chemical repertoire publication-title: Molecules contributor: fullname: Diafa – volume: 11 start-page: 1210 year: 2016 ident: key 20180801083947_B17 article-title: Improving polymerase activity with unnatural substrates by sampling mutations in homologous protein architectures publication-title: ACS Chem. Biol. contributor: fullname: Dunn – volume: 54 start-page: 11930 year: 2015 ident: key 20180801083947_B34 article-title: The expanded genetic alphabet publication-title: Angew. Chem. Int. Ed. Engl. contributor: fullname: Malyshev – volume: 21 start-page: 5009 year: 2015 ident: key 20180801083947_B37 article-title: Isoguanine and 5-methyl-isocytosine bases, in vitro and in vivo publication-title: Chem. A Eur. J. contributor: fullname: Bande – volume: 4 start-page: 183 year: 2012 ident: key 20180801083947_B14 article-title: Darwinian evolution of an alternative genetic system provides support for TNA as an RNA progenitor publication-title: Nat. Chem. contributor: fullname: Yu – volume: 81 start-page: 2302 year: 2016 ident: key 20180801083947_B27 article-title: A scalable synthesis of α-L-threose nucleic acid monomers publication-title: J. Org. Chem. contributor: fullname: Sau – volume: 26 start-page: 3271 year: 2016 ident: key 20180801083947_B30 article-title: A one-pot synthesis of a-L-threofuranosyl nucleoside triphosphates publication-title: Bioorg. Med. Chem. Lett. contributor: fullname: Sau – volume: 127 start-page: 2802 year: 2005 ident: key 20180801083947_B13 article-title: An in vitro selection system for TNA publication-title: J. Am. Chem. Soc. contributor: fullname: Ichida – volume: 136 start-page: 2033 year: 2014 ident: key 20180801083947_B28 article-title: Synthesis and nonenzymatic template-directed polymerization of 2΄-amino-2΄-deoxythreose nucleotides publication-title: J. Am. Chem. Soc. contributor: fullname: Bain – volume: 82 start-page: 1082 year: 2010 ident: key 20180801083947_B26 article-title: Incorporation of the fluorescent ribonucleotide analogue tCTP by T7 RNA polymerase publication-title: Anal Chem contributor: fullname: Stengel – volume: 90 start-page: 804 year: 1993 ident: key 20180801083947_B18 article-title: Crystal structure of an oligonucleotide duplex containing GG base pairs: influence of mispairing on DNA backbone conformation publication-title: Proc. Natl. Acad. Sci. USA contributor: fullname: Skelly – volume: 7 start-page: 11235 year: 2016 ident: key 20180801083947_B16 article-title: A general strategy for expanding polymerase function by droplet microfluidics publication-title: Nat. Commun. contributor: fullname: Larsen – volume: 290 start-page: 1347 year: 2000 ident: key 20180801083947_B2 article-title: Chemical etiology of nucleic acid structure: the alpha-threofuranosyl-(3΄–>2΄) oligonucleotide system publication-title: Science contributor: fullname: Schöning – volume: 31 start-page: 6221 year: 2003 ident: key 20180801083947_B10 article-title: Recognition of threosyl nucleotides by DNA and RNA polymerases publication-title: Nucleic Acids Res contributor: fullname: Kempeneers – volume: 65 start-page: 289 year: 2007 ident: key 20180801083947_B4 article-title: Experimental evidence that GNA and TNA were not sequential polymers in the prebiotic evolution of RNA publication-title: J. Mol. Evol. contributor: fullname: Yang – volume: 100 start-page: 2047 year: 2000 ident: key 20180801083947_B31 article-title: Syntheses of Nucleoside Triphosphates publication-title: Chem. Rev. contributor: fullname: Burgess – volume: 127 start-page: 7427 year: 2005 ident: key 20180801083947_B11 article-title: Kinetic analysis of an efficient DNA-dependent TNA polymerase publication-title: J. Am. Chem. Soc. contributor: fullname: Horhota – volume: 85 start-page: 4111 year: 2002 ident: key 20180801083947_B3 article-title: The a-L-Threofurnaosyl-(3΄-2΄)-oligonucleotide system ('TNA'): synthesis and pairing properties publication-title: Helv. Chim. Acta contributor: fullname: Schöning – volume: 33 start-page: 5219 year: 2005 ident: key 20180801083947_B12 article-title: High fidelity TNA synthesis by therminator polymerase publication-title: Nucleic Acids Res contributor: fullname: Ichida – volume: 37 start-page: 3924 year: 2009 ident: key 20180801083947_B23 article-title: Highly efficient incorporation of the fluorescent nucleotide analogs tC and tCo by Kenow fragment publication-title: Nucleic Acids Res contributor: fullname: Sandin – volume: 125 start-page: 9274 year: 2003 ident: key 20180801083947_B9 article-title: TNA synthesis by DNA polymerases publication-title: J. Am. Chem. Soc. contributor: fullname: Chaput – volume: 2 start-page: 615 year: 2007 ident: key 20180801083947_B20 article-title: Synthesis and oligonucleotide incorporation of fluorescent cytosine analogue tC: a promising nucleic acid probe publication-title: Nat. Protoc. contributor: fullname: Sandin – volume: 336 start-page: 341 year: 2012 ident: key 20180801083947_B15 article-title: Synthetic genetic polymers capable of heredity and evolution publication-title: Science contributor: fullname: Pinheiro – volume: 117 start-page: 3873 year: 1995 ident: key 20180801083947_B19 article-title: Tricyclic 2-deoxycytidine analogs: syntheses and incorporation into oligodeoxynucleotides which have enhanced binding to complementary RNA publication-title: J. Am. Chem. Soc. contributor: fullname: Lin |
SSID | ssj0014154 |
Score | 2.41234 |
Snippet | Threose nucleic acid (TNA) is an artificial genetic polymer capable of undergoing Darwinian evolution to produce aptamers with affinity to specific targets.... |
SourceID | pubmedcentral proquest crossref pubmed |
SourceType | Open Access Repository Aggregation Database Index Database |
StartPage | 5629 |
SubjectTerms | Base Pairing Biomimetic Materials - chemistry Chemical Biology and Nucleic Acid Chemistry Fluorescence Guanine - chemistry Hydrophobic and Hydrophilic Interactions Kinetics Nucleic Acids - chemistry Nucleic Acids - genetics Phenothiazines - chemistry Polyphosphates - chemistry Tetroses - chemistry Time Factors Transcription, Genetic |
Title | Synthesis and polymerase activity of a fluorescent cytidine TNA triphosphate analogue |
URI | https://www.ncbi.nlm.nih.gov/pubmed/28472363 https://search.proquest.com/docview/1896042233 https://pubmed.ncbi.nlm.nih.gov/PMC5449585 |
Volume | 45 |
hasFullText | 1 |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3da9swED_avmwvo1_bsn6gsdE31631YekxhJZSaDdYAnkzkiwvYYkcYgea_74nOy5L-9YXY2xZmLvj7qfT6XcAP43Mba6EjRjPWcRoYSIlrY6Es9rZ8NCFw8kPj-JuxO7HfLwDvDsL0xTtWzO99LP5pZ9OmtrKxdzGXZ1Y_PthwBnCesnjXdhNKe2W6JutA4xILWdUQ7HJZMdJqmjs9TL----JitClL_jlhAq6HZDeoMzXxZL_RZ_bffi0gY2k3_7eAew4fwhHfY9L5vmaXJCmkLPJkB_Ch0HXxO0IRn_WHiFeNa2I9jlZlLN1yEJVjoQDDaFvBCkLokkxW5XLltmJ2HU9xYjmyPCxT2p0KpOyWkwQk-IUbarnGEa3N8PBXbTppBBZmso6MlzIwgnLuVBMU2XwNmeKXWmL2pHXHJ2ck6lkmheKu4QanhQ4isnc2IJq-hn2fOndVyA00blFD8olAoMrlRrLEse40hqBQyFYD3504swWLWFG1m500wzln7Xy78H3TtIZSiRsUmjvylWVXctAF4OghfbgSyv5l3k6lfUg3dLJy4DAlb39Bk2o4czemMy3d395Ah-TENFDAiY5hb16uXJniEdqc96s488bK8Tr8Nf4GcXG5q4 |
link.rule.ids | 230,315,733,786,790,870,891,27955,27956,53825,53827 |
linkProvider | National Library of Medicine |
linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1bb9MwFD4a42G8MNi4dNyMQLyl2eJLnceqYiqwVki0aG-R7Ti0WutUTSpRfj3HcTPR8QRvUeJYST7nnM_Hx98BeK9lbvJUmIjxnEWMFjpKpVGRsEZZ409avzl5NBbDKft8za8PgLd7YZqkfaPnXbdYdt181uRWrpYmbvPE4q-jAWdI6yWP78F9_F8T3k7Sd4sH6JOCalQjsslkq0qa0tipdfzj5icVvk6ft8wJFXTfJf3FM--mS_7hfy6P4Xv75CHt5Ka7qXXX_Loj6vjPr_YIHu4YKemHy4_hwLoTOO07nI0vt-QDaXJEm-D7CRwN2vpwpzD9tnXIHqt5RZTLyapcbH2Aq7LE75XwJSlIWRBFisWmXAfRKGK29RydpSWTcZ_UaK9mZbWaId3FLkIU6QlMLz9OBsNoV6QhMrQn60hzIQsrDOciZYqmGg9zlrJzZRB4ecHRflrZk0zxIuU2oZonBbZiMtemoIo-hUNXOvscCE1UbtA4c4mc4zztacMSy3iqFHKSQrAOvGtxylZBiyMLa-g0Q2CzAGwH3rYQZvhF_PqHcrbcVNmF9Eo0yIdoB54FSG_7acdCB3p7YN828DLc-1cQwkaOewfZ2X_f-QaOhpPRVXb1afzlBTxIPHHwcZ7kJRzW6419hbSn1q-bQf4bJ4IGqg |
linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3fb9MwED7BkIAXBhuDwgAjEG9ptvhHnMeqWzV-rJrEKk28RLbj0GqtEzWpRPnrOSfNtI63vUWJYyX5nLvP5_N3AJ-1zEyWCBMwnrGA0VwHiTQqENYoa_xJ6zcnn4_F2YR9u-JXt0p9NUn7Rs_6br7ou9m0ya0sFybs8sTCi_MhZ0jrJQ_LLA8fwiP8Z6O4m6hvFhDQL7XKUY3QJpOdMmlCQ6eW4e_rP1T4Wn3eOkdU0G239B_XvJsyecsHjXbhV_f0berJdX9V6775e0fY8V6v9xyebZgpGbRNXsAD6_Zgf-BwVr5Yky-kyRVtgvB78GTY1Ynbh8nPtUMWWc0qolxGymK-9oGuyhK_Z8KXpiBFThTJ56ti2YpHEbOuZ-g0LbkcD0iNdmtaVOUUaS920UaTXsJkdHo5PAs2xRoCQ2NZB5oLmVthOBcJUzTReJixhB0pgwNAHnO0o1bGkimeJ9xGVPMox1ZMZtrkVNED2HGFs6-B0EhlBo00l8g9jpJYGxZZxhOlkJvkgvXgU4dVWraaHGm7lk5TBDdtwe3Bxw7GFL-IXwdRzharKj2WXpEGeRHtwasW1pt-uvHQg3gL8JsGXo57-wrC2Mhyb2B7c-87P8Dji5NR-uPr-PtbeBp5_uDDPdEh7NTLlX2H7KfW75tx_g9Nygkq |
openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Synthesis+and+polymerase+activity+of+a+fluorescent+cytidine+TNA+triphosphate+analogue&rft.jtitle=Nucleic+acids+research&rft.au=Mei%2C+Hui&rft.au=Shi%2C+Changhua&rft.au=Jimenez%2C+Randi+M.&rft.au=Wang%2C+Yajun&rft.date=2017-06-02&rft.issn=0305-1048&rft.eissn=1362-4962&rft.volume=45&rft.issue=10&rft.spage=5629&rft.epage=5638&rft_id=info:doi/10.1093%2Fnar%2Fgkx368&rft.externalDBID=n%2Fa&rft.externalDocID=10_1093_nar_gkx368 |
thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0305-1048&client=summon |
thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0305-1048&client=summon |
thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0305-1048&client=summon |