{"id":"https://openalex.org/W3005148232","doi":"https://doi.org/10.1021/jo060300k","title":"Design and Synthesis of a Photocleavable Fluorescent Nucleotide 3\u2018-O-Allyl-dGTP-PC-Bodipy-FL-510 as a Reversible Terminator for DNA Sequencing by Synthesis","display_name":"Design and Synthesis of a Photocleavable Fluorescent Nucleotide 3\u2018-O-Allyl-dGTP-PC-Bodipy-FL-510 as a Reversible Terminator for DNA Sequencing by Synthesis","publication_year":2006,"publication_date":"2006-03-24","ids":{"openalex":"https://openalex.org/W3005148232","doi":"https://doi.org/10.1021/jo060300k","mag":"3005148232","pmid":"https://pubmed.ncbi.nlm.nih.gov/16599623"},"language":"en","primary_location":{"id":"doi:10.1021/jo060300k","doi":"https://doi.org/10.1021/jo060300k","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo060300k","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of Organic Chemistry","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5100832475","display_name":"Qinglin Meng","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I78577930","display_name":"Columbia University","ror":"https://ror.org/00hj8s172","country_code":"US","type":"education","lineage":["https://openalex.org/I78577930"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Qinglin Meng","raw_affiliation_strings":["Columbia Genome Center, Columbia University College of Physicians and Surgeons, New York, New York 10032, and Departments of Chemical Engineering, Chemistry, and Biomedical Engineering, Columbia University, New York, New York 10027"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Columbia Genome Center, Columbia University College of Physicians and Surgeons, New York, New York 10032, and Departments of Chemical Engineering, Chemistry, and Biomedical Engineering, Columbia University, New York, New York 10027","institution_ids":["https://openalex.org/I78577930"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5100374585","display_name":"Dae Hyun Kim","orcid":"https://orcid.org/0000-0003-4391-5502","observed_orcids":["https://orcid.org/0000-0003-4391-5502"]},"institutions":[{"id":"https://openalex.org/I78577930","display_name":"Columbia University","ror":"https://ror.org/00hj8s172","country_code":"US","type":"education","lineage":["https://openalex.org/I78577930"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Dae Hyun Kim","raw_affiliation_strings":["Columbia Genome Center, Columbia University College of Physicians and Surgeons, New York, New York 10032, and Departments of Chemical Engineering, Chemistry, and Biomedical Engineering, Columbia University, New York, New York 10027"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Columbia Genome Center, Columbia University College of Physicians and Surgeons, New York, New York 10032, and Departments of Chemical Engineering, Chemistry, and Biomedical Engineering, Columbia University, New York, New York 10027","institution_ids":["https://openalex.org/I78577930"]}]},{"author_position":"middle","author":{"id":null,"display_name":"Xiaopeng Bai","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I78577930","display_name":"Columbia University","ror":"https://ror.org/00hj8s172","country_code":"US","type":"education","lineage":["https://openalex.org/I78577930"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Xiaopeng Bai","raw_affiliation_strings":["Columbia Genome Center, Columbia University College of Physicians and Surgeons, New York, New York 10032, and Departments of Chemical Engineering, Chemistry, and Biomedical Engineering, Columbia University, New York, New York 10027"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Columbia Genome Center, Columbia University College of Physicians and Surgeons, New York, New York 10032, and Departments of Chemical Engineering, Chemistry, and Biomedical Engineering, Columbia University, New York, New York 10027","institution_ids":["https://openalex.org/I78577930"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5055567545","display_name":"Lanrong Bi","orcid":"https://orcid.org/0000-0001-6624-8314","observed_orcids":["https://orcid.org/0000-0001-6624-8314"]},"institutions":[{"id":"https://openalex.org/I78577930","display_name":"Columbia University","ror":"https://ror.org/00hj8s172","country_code":"US","type":"education","lineage":["https://openalex.org/I78577930"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Lanrong Bi","raw_affiliation_strings":["Columbia Genome Center, Columbia University College of Physicians and Surgeons, New York, New York 10032, and Departments of Chemical Engineering, Chemistry, and Biomedical Engineering, Columbia University, New York, New York 10027"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Columbia Genome Center, Columbia University College of Physicians and Surgeons, New York, New York 10032, and Departments of Chemical Engineering, Chemistry, and Biomedical Engineering, Columbia University, New York, New York 10027","institution_ids":["https://openalex.org/I78577930"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5110885322","display_name":"Nicholas J. Turro","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I78577930","display_name":"Columbia University","ror":"https://ror.org/00hj8s172","country_code":"US","type":"education","lineage":["https://openalex.org/I78577930"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Nicholas J. Turro","raw_affiliation_strings":["Columbia Genome Center, Columbia University College of Physicians and Surgeons, New York, New York 10032, and Departments of Chemical Engineering, Chemistry, and Biomedical Engineering, Columbia University, New York, New York 10027"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Columbia Genome Center, Columbia University College of Physicians and Surgeons, New York, New York 10032, and Departments of Chemical Engineering, Chemistry, and Biomedical Engineering, Columbia University, New York, New York 10027","institution_ids":["https://openalex.org/I78577930"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5084552494","display_name":"Jingyue Ju","orcid":"https://orcid.org/0000-0002-4974-4241","observed_orcids":["https://orcid.org/0000-0002-4974-4241"]},"institutions":[{"id":"https://openalex.org/I78577930","display_name":"Columbia University","ror":"https://ror.org/00hj8s172","country_code":"US","type":"education","lineage":["https://openalex.org/I78577930"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Jingyue Ju","raw_affiliation_strings":["Columbia Genome Center, Columbia University College of Physicians and Surgeons, New York, New York 10032, and Departments of Chemical Engineering, Chemistry, and Biomedical Engineering, Columbia University, New York, New York 10027"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Columbia Genome Center, Columbia University College of Physicians and Surgeons, New York, New York 10032, and Departments of Chemical Engineering, Chemistry, and Biomedical Engineering, Columbia University, New York, New York 10027","institution_ids":["https://openalex.org/I78577930"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I78577930"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":2.3093,"has_fulltext":false,"cited_by_count":51,"citation_normalized_percentile":{"value":0.87801124,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":99},"biblio":{"volume":"71","issue":"8","first_page":"3248","last_page":"3252"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10432","display_name":"DNA and Nucleic Acid Chemistry","score":0.9843999743461609,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},"topics":[{"id":"https://openalex.org/T10432","display_name":"DNA and Nucleic Acid Chemistry","score":0.9843999743461609,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T10207","display_name":"Advanced biosensing and bioanalysis techniques","score":0.003700000001117587,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T11708","display_name":"Photochromic and Fluorescence Chemistry","score":0.002300000051036477,"subfield":{"id":"https://openalex.org/subfields/2505","display_name":"Materials Chemistry"},"field":{"id":"https://openalex.org/fields/25","display_name":"Materials Science"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/photocleavage","display_name":"photocleavage","score":0.6990000009536743},{"id":"https://openalex.org/keywords/next-generation-sequencing","display_name":"next-generation sequencing","score":0.8289999961853027}],"concepts":[{"id":"https://openalex.org/C178046730","wikidata":"https://www.wikidata.org/wiki/Q331824","display_name":"Terminator (solar)","level":3,"score":0.7615256905555725},{"id":"https://openalex.org/C2781374752","wikidata":"https://www.wikidata.org/wiki/Q679174","display_name":"BODIPY","level":3,"score":0.6442360281944275},{"id":"https://openalex.org/C552990157","wikidata":"https://www.wikidata.org/wiki/Q7430","display_name":"DNA","level":2,"score":0.5697266459465027},{"id":"https://openalex.org/C512185932","wikidata":"https://www.wikidata.org/wiki/Q28745","display_name":"Nucleotide","level":3,"score":0.5648180246353149},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.5264778137207031},{"id":"https://openalex.org/C91881484","wikidata":"https://www.wikidata.org/wiki/Q191807","display_name":"Fluorescence","level":2,"score":0.45351922512054443},{"id":"https://openalex.org/C64241487","wikidata":"https://www.wikidata.org/wiki/Q5205774","display_name":"DNA synthesis","level":3,"score":0.4381873607635498},{"id":"https://openalex.org/C51679486","wikidata":"https://www.wikidata.org/wiki/Q380546","display_name":"DNA sequencing","level":3,"score":0.4307999014854431},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.42936816811561584},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.3689468801021576},{"id":"https://openalex.org/C12554922","wikidata":"https://www.wikidata.org/wiki/Q7100","display_name":"Biophysics","level":1,"score":0.3219580054283142},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.23832401633262634},{"id":"https://openalex.org/C86803240","wikidata":"https://www.wikidata.org/wiki/Q420","display_name":"Biology","level":0,"score":0.23353800177574158},{"id":"https://openalex.org/C104317684","wikidata":"https://www.wikidata.org/wiki/Q7187","display_name":"Gene","level":2,"score":0.1343955099582672},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.11650204658508301},{"id":"https://openalex.org/C116403925","wikidata":"https://www.wikidata.org/wiki/Q162219","display_name":"Ionosphere","level":2,"score":0.0},{"id":"https://openalex.org/C1276947","wikidata":"https://www.wikidata.org/wiki/Q333","display_name":"Astronomy","level":1,"score":0.0},{"id":"https://openalex.org/C62520636","wikidata":"https://www.wikidata.org/wiki/Q944","display_name":"Quantum mechanics","level":1,"score":0.0}],"mesh":[{"descriptor_ui":"D001483","descriptor_name":"Base Sequence","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D003848","descriptor_name":"Deoxyguanine Nucleotides","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D003848","descriptor_name":"Deoxyguanine Nucleotides","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D003848","descriptor_name":"Deoxyguanine Nucleotides","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D004259","descriptor_name":"DNA-Directed DNA Polymerase","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D005456","descriptor_name":"Fluorescent Dyes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D005456","descriptor_name":"Fluorescent Dyes","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D005456","descriptor_name":"Fluorescent Dyes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D010777","descriptor_name":"Photochemistry","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/jo060300k","doi":"https://doi.org/10.1021/jo060300k","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo060300k","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of Organic Chemistry","raw_type":"journal-article"},{"id":"pmid:16599623","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/16599623","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of organic chemistry","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G5579858698","display_name":"Genomic Approaches to Neuronal Diversity and Plasticity","funder_award_id":"P50HG002806","funder_id":"https://openalex.org/F4320337348","funder_display_name":"National Human Genome Research Institute"},{"id":"https://openalex.org/G6960622525","display_name":"An Integrated System for DNA Sequencing by Synthesis","funder_award_id":"R01HG003582","funder_id":"https://openalex.org/F4320337348","funder_display_name":"National Human Genome Research Institute"}],"funders":[{"id":"https://openalex.org/F4320337348","display_name":"National Human Genome Research Institute","ror":"https://ror.org/00baak391"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":4,"referenced_works":["https://openalex.org/W1984603555","https://openalex.org/W2014020458","https://openalex.org/W2022628495","https://openalex.org/W2075155566"],"related_works":["https://openalex.org/W2075155566","https://openalex.org/W1977332303","https://openalex.org/W4254945764","https://openalex.org/W2126057141","https://openalex.org/W2788809525","https://openalex.org/W2943300533","https://openalex.org/W2121517408","https://openalex.org/W2082631942","https://openalex.org/W2888913328","https://openalex.org/W2137348240"],"abstract_inverted_index":{"DNA":[0,21,51,56,118,131],"sequencing":[1,22],"by":[2,50,70,84],"synthesis":[3,30],"(SBS)":[4],"using":[5,85],"reversible":[6,41],"fluorescent":[7,35],"nucleotide":[8,36,46],"terminators":[9],"is":[10,47,67,79],"potentially":[11],"an":[12],"efficient":[13],"approach":[14,128],"to":[15,58,92,98,111],"address":[16],"the":[17,27,60,65,76,100,121],"limitations":[18],"of":[19,31,105,116,123],"current":[20],"techniques.":[23],"Here,":[24],"we":[25],"report":[26],"design":[28],"and":[29,75,81],"a":[32,40,54,86,94,113,117,126],"3'-O-allyl":[33],"photocleavable":[34],"analogue,":[37],"3'-O-allyl-dGTP-PC-Bodipy-FL-510,":[38],"as":[39,125],"terminator":[42],"for":[43,129],"SBS.":[44],"The":[45],"efficiently":[48,82],"incorporated":[49],"polymerase":[52,61,101],"into":[53],"growing":[55],"strand":[57],"terminate":[59],"reaction.":[62,102],"After":[63],"that,":[64],"fluorophore":[66],"photocleaved":[68],"quantitatively":[69],"irradiation":[71],"at":[72],"355":[73],"nm,":[74],"allyl":[77],"group":[78,97],"rapidly":[80],"removed":[83],"Pd-catalyzed":[87],"reaction":[88],"under":[89],"DNA-compatible":[90],"conditions":[91],"regenerate":[93],"free":[95],"3'-OH":[96],"reinitiate":[99],"Two":[103],"cycles":[104],"such":[106],"steps":[107],"were":[108],"successfully":[109],"demonstrated":[110],"sequence":[112],"homopolymeric":[114],"region":[115],"template,":[119],"facilitating":[120],"development":[122],"SBS":[124],"viable":[127],"high-throughput":[130],"sequencing.":[132]},"counts_by_year":[{"year":2025,"cited_by_count":2},{"year":2024,"cited_by_count":3},{"year":2021,"cited_by_count":1},{"year":2019,"cited_by_count":1},{"year":2017,"cited_by_count":1},{"year":2015,"cited_by_count":6},{"year":2014,"cited_by_count":1},{"year":2013,"cited_by_count":5},{"year":2012,"cited_by_count":6}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2020-02-14T00:00:00"}