{"id":"https://openalex.org/W1978656549","doi":"https://doi.org/10.1021/ja206023e","title":"Protein Glycoengineering Enabled by the Versatile Synthesis of Aminooxy Glycans and the Genetically Encoded Aldehyde Tag","display_name":"Protein Glycoengineering Enabled by the Versatile Synthesis of Aminooxy Glycans and the Genetically Encoded Aldehyde Tag","publication_year":2011,"publication_date":"2011-08-25","ids":{"openalex":"https://openalex.org/W1978656549","doi":"https://doi.org/10.1021/ja206023e","mag":"1978656549","pmid":"https://pubmed.ncbi.nlm.nih.gov/21866965","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/3187659"},"language":"en","primary_location":{"id":"doi:10.1021/ja206023e","doi":"https://doi.org/10.1021/ja206023e","is_oa":true,"landing_page_url":"https://doi.org/10.1021/ja206023e","pdf_url":"https://pubs.acs.org/doi/pdf/10.1021/ja206023e","source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","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":"other-oa","license_id":"https://openalex.org/licenses/other-oa","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":true,"oa_status":"hybrid","oa_url":"https://pubs.acs.org/doi/pdf/10.1021/ja206023e","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5072130421","display_name":"Jason E. Hudak","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I1344073410","display_name":"Howard Hughes Medical Institute","ror":"https://ror.org/006w34k90","country_code":"US","type":"facility","lineage":["https://openalex.org/I1344073410"]},{"id":"https://openalex.org/I95457486","display_name":"University of California, Berkeley","ror":"https://ror.org/01an7q238","country_code":"US","type":"education","lineage":["https://openalex.org/I95457486"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Jason E. Hudak","raw_affiliation_strings":["Departments of Chemistry and Molecular and Cell Biology and Howard Hughes Medical Institute, University of California, Berkeley, California, 94720"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departments of Chemistry and Molecular and Cell Biology and Howard Hughes Medical Institute, University of California, Berkeley, California, 94720","institution_ids":["https://openalex.org/I1344073410","https://openalex.org/I95457486"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5030676459","display_name":"Helen H. Yu","orcid":"https://orcid.org/0000-0001-9881-8414","observed_orcids":["https://orcid.org/0000-0001-9881-8414"]},"institutions":[{"id":"https://openalex.org/I1344073410","display_name":"Howard Hughes Medical Institute","ror":"https://ror.org/006w34k90","country_code":"US","type":"facility","lineage":["https://openalex.org/I1344073410"]},{"id":"https://openalex.org/I95457486","display_name":"University of California, Berkeley","ror":"https://ror.org/01an7q238","country_code":"US","type":"education","lineage":["https://openalex.org/I95457486"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Helen H. Yu","raw_affiliation_strings":["Departments of Chemistry and Molecular and Cell Biology and Howard Hughes Medical Institute, University of California, Berkeley, California, 94720"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departments of Chemistry and Molecular and Cell Biology and Howard Hughes Medical Institute, University of California, Berkeley, California, 94720","institution_ids":["https://openalex.org/I1344073410","https://openalex.org/I95457486"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5088409133","display_name":"Carolyn Ruth Bertozzi","orcid":"https://orcid.org/0000-0003-4482-2754","observed_orcids":["https://orcid.org/0000-0003-4482-2754"]},"institutions":[{"id":"https://openalex.org/I1344073410","display_name":"Howard Hughes Medical Institute","ror":"https://ror.org/006w34k90","country_code":"US","type":"facility","lineage":["https://openalex.org/I1344073410"]},{"id":"https://openalex.org/I95457486","display_name":"University of California, Berkeley","ror":"https://ror.org/01an7q238","country_code":"US","type":"education","lineage":["https://openalex.org/I95457486"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Carolyn R. Bertozzi","raw_affiliation_strings":["Departments of Chemistry and Molecular and Cell Biology and Howard Hughes Medical Institute, University of California, Berkeley, California, 94720"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departments of Chemistry and Molecular and Cell Biology and Howard Hughes Medical Institute, University of California, Berkeley, California, 94720","institution_ids":["https://openalex.org/I1344073410","https://openalex.org/I95457486"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":["https://openalex.org/A5088409133"],"corresponding_institution_ids":["https://openalex.org/I1344073410","https://openalex.org/I95457486"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":{"value":4500,"currency":"USD","value_usd":4500},"fwci":5.4138,"has_fulltext":false,"cited_by_count":93,"citation_normalized_percentile":{"value":0.96590192,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":93,"max":100},"biblio":{"volume":"133","issue":"40","first_page":"16127","last_page":"16135"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10835","display_name":"Carbohydrate Chemistry and Synthesis","score":0.5522000193595886,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T10835","display_name":"Carbohydrate Chemistry and Synthesis","score":0.5522000193595886,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T10602","display_name":"Glycosylation and Glycoproteins Research","score":0.3400999903678894,"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/T11440","display_name":"Click Chemistry and Applications","score":0.0714000016450882,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/oxime-linkage","display_name":"oxime linkage","score":0.7080000042915344},{"id":"https://openalex.org/keywords/formylglycine","display_name":"formylglycine","score":0.9330000281333923},{"id":"https://openalex.org/keywords/site-specific-glycosylation","display_name":"site-specific glycosylation","score":0.7820000052452087},{"id":"https://openalex.org/keywords/human-growth-hormone","display_name":"human growth hormone","score":0.8379999995231628},{"id":"https://openalex.org/keywords/glycan-synthesis","display_name":"glycan synthesis","score":0.6359999775886536}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9355848431587219},{"id":"https://openalex.org/C206212055","wikidata":"https://www.wikidata.org/wiki/Q2553138","display_name":"Glycan","level":3,"score":0.679083526134491},{"id":"https://openalex.org/C2779825165","wikidata":"https://www.wikidata.org/wiki/Q101497","display_name":"Aldehyde","level":3,"score":0.6017007827758789},{"id":"https://openalex.org/C51456166","wikidata":"https://www.wikidata.org/wiki/Q182726","display_name":"Genetically modified organism","level":3,"score":0.45036906003952026},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.400179922580719},{"id":"https://openalex.org/C70721500","wikidata":"https://www.wikidata.org/wiki/Q177005","display_name":"Computational biology","level":1,"score":0.3406415581703186},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.3405113220214844},{"id":"https://openalex.org/C108625454","wikidata":"https://www.wikidata.org/wiki/Q187126","display_name":"Glycoprotein","level":2,"score":0.282227098941803},{"id":"https://openalex.org/C104317684","wikidata":"https://www.wikidata.org/wiki/Q7187","display_name":"Gene","level":2,"score":0.27872610092163086},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.07529005408287048},{"id":"https://openalex.org/C86803240","wikidata":"https://www.wikidata.org/wiki/Q420","display_name":"Biology","level":0,"score":0.0}],"mesh":[{"descriptor_ui":"D000447","descriptor_name":"Aldehydes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D000606","descriptor_name":"Amino Sugars","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D000606","descriptor_name":"Amino Sugars","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D006023","descriptor_name":"Glycoproteins","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D006031","descriptor_name":"Glycosylation","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D006801","descriptor_name":"Humans","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008958","descriptor_name":"Models, Molecular","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D010091","descriptor_name":"Oximes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D011994","descriptor_name":"Recombinant Proteins","qualifier_ui":"Q000235","qualifier_name":"genetics","is_major_topic":false},{"descriptor_ui":"D011994","descriptor_name":"Recombinant Proteins","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D019382","descriptor_name":"Human Growth Hormone","qualifier_ui":"Q000235","qualifier_name":"genetics","is_major_topic":false},{"descriptor_ui":"D019382","descriptor_name":"Human Growth Hormone","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true}],"locations_count":4,"locations":[{"id":"doi:10.1021/ja206023e","doi":"https://doi.org/10.1021/ja206023e","is_oa":true,"landing_page_url":"https://doi.org/10.1021/ja206023e","pdf_url":"https://pubs.acs.org/doi/pdf/10.1021/ja206023e","source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","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":"other-oa","license_id":"https://openalex.org/licenses/other-oa","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"journal-article"},{"id":"pmh:oai:europepmc.org:2192132","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/3187659","pdf_url":null,"source":{"id":"https://openalex.org/S4306400806","display_name":"Europe PMC (PubMed Central)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1303153112","host_organization_name":"European Bioinformatics Institute","host_organization_lineage":["https://openalex.org/I1303153112"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":null,"raw_type":"Text"},{"id":"pmh:oai:pubmedcentral.nih.gov:3187659","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/3187659","pdf_url":null,"source":{"id":"https://openalex.org/S2764455111","display_name":"PubMed Central","issn_l":null,"issn":null,"is_oa":true,"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":"J Am Chem Soc","raw_type":"Text"},{"id":"pmid:21866965","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/21866965","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":"Journal of the American Chemical Society","raw_type":"Journal Article"}],"best_oa_location":{"id":"doi:10.1021/ja206023e","doi":"https://doi.org/10.1021/ja206023e","is_oa":true,"landing_page_url":"https://doi.org/10.1021/ja206023e","pdf_url":"https://pubs.acs.org/doi/pdf/10.1021/ja206023e","source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","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":"other-oa","license_id":"https://openalex.org/licenses/other-oa","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"journal-article"},"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G7689501090","display_name":"Chemical Cell Surface Engineering","funder_award_id":"R01GM059907","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"}],"funders":[{"id":"https://openalex.org/F4320306076","display_name":"National Science Foundation","ror":"https://ror.org/021nxhr62"},{"id":"https://openalex.org/F4320306082","display_name":"Howard Hughes Medical Institute","ror":"https://ror.org/006w34k90"},{"id":"https://openalex.org/F4320332161","display_name":"National Institutes of Health","ror":"https://ror.org/01cwqze88"},{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"}],"has_content":{"grobid_xml":false,"pdf":true},"content_urls":{"pdf":"https://content.openalex.org/works/W1978656549.pdf"},"referenced_works_count":68,"referenced_works":["https://openalex.org/W1918364069","https://openalex.org/W1966202144","https://openalex.org/W1966992916","https://openalex.org/W1974060054","https://openalex.org/W1975251855","https://openalex.org/W1976652206","https://openalex.org/W1979108979","https://openalex.org/W1982143526","https://openalex.org/W1983639577","https://openalex.org/W1987081782","https://openalex.org/W1989730031","https://openalex.org/W1993771099","https://openalex.org/W1997674330","https://openalex.org/W1997919302","https://openalex.org/W1998393627","https://openalex.org/W2000891397","https://openalex.org/W2001035270","https://openalex.org/W2003560074","https://openalex.org/W2007058937","https://openalex.org/W2010621614","https://openalex.org/W2013209387","https://openalex.org/W2016330877","https://openalex.org/W2018211219","https://openalex.org/W2018885419","https://openalex.org/W2027170262","https://openalex.org/W2030625213","https://openalex.org/W2031249985","https://openalex.org/W2035618963","https://openalex.org/W2036493629","https://openalex.org/W2043399212","https://openalex.org/W2047401334","https://openalex.org/W2050626445","https://openalex.org/W2052061962","https://openalex.org/W2055712556","https://openalex.org/W2060270009","https://openalex.org/W2062204886","https://openalex.org/W2063568398","https://openalex.org/W2064881812","https://openalex.org/W2070888873","https://openalex.org/W2073036218","https://openalex.org/W2073627889","https://openalex.org/W2076709027","https://openalex.org/W2080944921","https://openalex.org/W2084735047","https://openalex.org/W2087779058","https://openalex.org/W2088600448","https://openalex.org/W2089392594","https://openalex.org/W2090371323","https://openalex.org/W2092014932","https://openalex.org/W2093217904","https://openalex.org/W2100773900","https://openalex.org/W2102076364","https://openalex.org/W2105132980","https://openalex.org/W2117398821","https://openalex.org/W2118292315","https://openalex.org/W2120013398","https://openalex.org/W2121017466","https://openalex.org/W2131032705","https://openalex.org/W2135044072","https://openalex.org/W2140433352","https://openalex.org/W2149640957","https://openalex.org/W2151709132","https://openalex.org/W2155715825","https://openalex.org/W2156117820","https://openalex.org/W2165262749","https://openalex.org/W2949422872","https://openalex.org/W2950168366","https://openalex.org/W4297851190"],"related_works":["https://openalex.org/W7099983719","https://openalex.org/W2170357664","https://openalex.org/W2965281762","https://openalex.org/W6931659420","https://openalex.org/W4307179948","https://openalex.org/W1983639577","https://openalex.org/W2125272176","https://openalex.org/W3119256538","https://openalex.org/W2144508700","https://openalex.org/W4283367158"],"abstract_inverted_index":{"Homogeneously":[0],"glycosylated":[1,41,110],"proteins":[2,42,53],"are":[3],"important":[4],"targets":[5],"for":[6,10],"fundamental":[7],"research":[8],"and":[9,101],"biopharmaceutical":[11],"development.":[12],"The":[13],"use":[14],"of":[15,30,47,112],"unnatural":[16],"protein-glycan":[17],"linkages":[18],"bearing":[19],"structural":[20],"similarity":[21],"to":[22,50,65],"their":[23],"native":[24],"counterparts":[25],"can":[26,96],"accelerate":[27],"the":[28,59,71,105,113],"synthesis":[29],"glycoengineered":[31],"proteins.":[32],"Here":[33],"we":[34],"report":[35],"an":[36],"approach":[37],"toward":[38],"generating":[39],"homogeneously":[40],"that":[43,88,95],"involves":[44],"chemical":[45],"attachment":[46],"aminooxy":[48,80],"glycans":[49,81],"recombinantly":[51],"produced":[52],"via":[54],"oxime":[55],"linkages.":[56],"We":[57,103],"employed":[58],"recently":[60],"introduced":[61],"aldehyde":[62],"tag":[63],"method":[64,106],"obtain":[66],"a":[67,76,85],"recombinant":[68],"protein":[69],"with":[70],"aldehyde-bearing":[72],"formylglycine":[73],"residue":[74],"at":[75],"specific":[77],"site.":[78],"Complex":[79],"were":[82],"synthesized":[83],"using":[84],"new":[86],"route":[87],"features":[89],"N-pentenoyl":[90],"hydroxamates":[91],"as":[92],"key":[93],"intermediates":[94],"be":[97],"readily":[98],"elaborated":[99],"chemically":[100],"enzymatically.":[102],"demonstrated":[104],"by":[107],"constructing":[108],"site-specifically":[109],"variants":[111],"human":[114],"growth":[115],"hormone.":[116]},"counts_by_year":[{"year":2025,"cited_by_count":5},{"year":2024,"cited_by_count":4},{"year":2023,"cited_by_count":2},{"year":2022,"cited_by_count":2},{"year":2021,"cited_by_count":3},{"year":2020,"cited_by_count":5},{"year":2019,"cited_by_count":2},{"year":2018,"cited_by_count":5},{"year":2017,"cited_by_count":7},{"year":2016,"cited_by_count":8},{"year":2015,"cited_by_count":11},{"year":2014,"cited_by_count":16},{"year":2013,"cited_by_count":10},{"year":2012,"cited_by_count":11}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}