{"corpus_id":90151186,"paper_sha":"6226870e7f864ee6acebe398be2ad8029e177672","doi":"10.5458/jag.jag.JAG-2017_010","arxiv_id":null,"pmid":34354501,"pmcid":"8056936","mag_id":2751153055,"dblp_id":null,"acl_id":null,"title":"Enzymatic Synthesis of 1,5-Anhydro-4-O-β-D-glucopyranosyl-D-fructose Using Cellobiose Phosphorylase and Its Spontaneous Decomposition via β-Elimination","year":2017,"publication_date":"2017-11-20","venue":"Journal of Applied Glycoscience","journal":{"name":"Journal of Applied Glycoscience","pages":"91 - 97","volume":"64"},"journal_issn":null,"journal_title":null,"publication_types":["JournalArticle"],"pubmed_pub_types":["Journal Article"],"s2_fields_of_study":["Medicine","Chemistry"],"reference_count":25,"citation_count":5,"influential_citation_count":0,"is_open_access":true,"arxiv_categories":null,"arxiv_license":null,"arxiv_journal_ref":null,"mesh_headings":null,"chemicals":null,"comments_corrections":null,"source_flags":5,"s2_open_access_pdf_url":"https://www.jstage.jst.go.jp/article/jag/64/4/64_jag.JAG-2017_010/_pdf","s2_open_access_landing_url":"https://www.semanticscholar.org/paper/6226870e7f864ee6acebe398be2ad8029e177672","s2_open_access_license":"CCBYNC","s2_open_access_status":"GOLD","pmc_open_access_pdf_url":null,"pmc_open_access_landing_url":null,"pmc_open_access_license":null,"pmc_open_access_status":null,"unpaywall_open_access_pdf_url":null,"unpaywall_open_access_landing_url":null,"unpaywall_open_access_license":null,"unpaywall_open_access_status":null,"abstract":"Cellobiose phosphorylase from Cellvibrio gilvus was used to prepare 1,5-anhydro-4-O-β-D-glucopyranosyl-D-fructose [βGlc(1→4)AF] from 1,5-anhydro-D-fructose and α-D-glucose 1-phosphate. βGlc(1→4)AF decomposed into D-glucose and ascopyrone T via β-elimination. Higher pH and temperature caused faster decomposition. However, decomposition proceeded significantly even under mild conditions. For instance, the half-life of βGlc(1→4)AF was 17 h at 30 °C and pH 7.0. Because βGlc(1→4)AF is a mimic of cellulose, in which the C2 hydroxyl group is oxidized, such decomposition may occur in oxidized cellulose in nature. Here we propose a possible oxidizing pathway by which this occurs.","claims":[{"public_id":"cl_a22f35678011ed4ed2738e576f9fab32","status":"active","text":"Cellobiose phosphorylase from Cellvibrio gilvus was used to prepare 1,5-anhydro-4-O-β-D-glucopyranosyl-D-fructose (βGlc(1→4)AF) from 1,5-anhydro-D-fructose and α-D-glucose 1-phosphate.","confidence":0.95,"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["review"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/claims/cl_a22f35678011ed4ed2738e576f9fab32"},{"public_id":"cl_eb8651ac5e7988c162be8a5f3fe66bd6","status":"active","text":"Higher pH and temperature caused faster decomposition of βGlc(1→4)AF.","confidence":0.9,"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["review"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/claims/cl_eb8651ac5e7988c162be8a5f3fe66bd6"},{"public_id":"cl_60681bbba9734936ba1858bbe2f205eb","status":"active","text":"The half-life of βGlc(1→4)AF was 17 h at 30 °C and pH 7.0.","confidence":0.95,"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["review"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/claims/cl_60681bbba9734936ba1858bbe2f205eb"},{"public_id":"cl_19a6fcbb0f284cb7eaff5a4e830133c6","status":"active","text":"βGlc(1→4)AF decomposed into D-glucose and ascopyrone T via β-elimination.","confidence":0.95,"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["review"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/claims/cl_19a6fcbb0f284cb7eaff5a4e830133c6"},{"public_id":"cl_657cdf6c68035206f05e13dc8ad84c82","status":"active","text":"βGlc(1→4)AF is a mimic of cellulose in which the C2 hydroxyl group is oxidized, and such decomposition may occur in oxidized cellulose in nature.","confidence":0.85,"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["review"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/claims/cl_657cdf6c68035206f05e13dc8ad84c82"}],"concepts":[{"public_id":"co_1980b84ee122aadbd6f30a971b95bd91","status":"active","name":"ascopyrone T","description":"The other decomposition product of βGlc(1→4)AF via β-elimination.","types":["product"],"aliases":[],"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["review"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_1980b84ee122aadbd6f30a971b95bd91"},{"public_id":"co_67f0ea8555838ce2d2562806411967c6","status":"active","name":"cellobiose phosphorylase","description":"An enzyme from Cellvibrio gilvus used to catalyze the synthesis of βGlc(1→4)AF.","types":["enzyme"],"aliases":[],"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["review"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_67f0ea8555838ce2d2562806411967c6"},{"public_id":"co_808312bdc0b39ff1cb4f75dc7911c8d1","status":"active","name":"1,5-anhydro-D-fructose","description":"One of the substrates used in the enzymatic synthesis of βGlc(1→4)AF.","types":["substrate"],"aliases":[],"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["review"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_808312bdc0b39ff1cb4f75dc7911c8d1"},{"public_id":"co_848db69a4d2b94886480b9aafb77cdbc","status":"active","name":"half-life","description":"The time required for half of βGlc(1→4)AF to decompose under given conditions; measured as 17 h at 30 °C and pH 7.0.","types":["measurement"],"aliases":[],"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["review"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_848db69a4d2b94886480b9aafb77cdbc"},{"public_id":"co_9507b8f9741bb9a165ebbdb4338e4aff","status":"active","name":"D-glucose","description":"One of the decomposition products of βGlc(1→4)AF via β-elimination.","types":["product"],"aliases":[],"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["review"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_9507b8f9741bb9a165ebbdb4338e4aff"},{"public_id":"co_a1203fca29c9542d8452f7cac3fcb0f4","status":"active","name":"β-elimination","description":"The reaction mechanism by which βGlc(1→4)AF decomposes into D-glucose and ascopyrone T.","types":["reaction"],"aliases":[],"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["review"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_a1203fca29c9542d8452f7cac3fcb0f4"},{"public_id":"co_a12c5f4200f763ef4f9fad6cf9514e42","status":"active","name":"pH","description":"A factor that influences the decomposition rate of βGlc(1→4)AF; higher pH accelerates decomposition.","types":["parameter"],"aliases":[],"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["review"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_a12c5f4200f763ef4f9fad6cf9514e42"},{"public_id":"co_c8ab6652dc81b033e1ef113fd5ffb2a6","status":"active","name":"1,5-anhydro-4-O-β-D-glucopyranosyl-D-fructose","description":"The disaccharide product synthesized from 1,5-anhydro-D-fructose and α-D-glucose 1-phosphate by cellobiose phosphorylase.","types":["compound"],"aliases":["βGlc(1→4)AF"],"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["review"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_c8ab6652dc81b033e1ef113fd5ffb2a6"},{"public_id":"co_ca81e654090308c9d02144b47540c60a","status":"active","name":"βGlc(1→4)AF","description":"The shorthand notation for 1,5-anhydro-4-O-β-D-glucopyranosyl-D-fructose, the synthesized disaccharide that undergoes β-elimination.","types":["compound"],"aliases":["1,5-anhydro-4-O-β-D-glucopyranosyl-D-fructose"],"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["review"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_ca81e654090308c9d02144b47540c60a"},{"public_id":"co_cb5a1dcb8fe051ed29407fec23c305bb","status":"active","name":"α-D-glucose 1-phosphate","description":"The second substrate used in the enzymatic synthesis of βGlc(1→4)AF.","types":["substrate"],"aliases":[],"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["review"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_cb5a1dcb8fe051ed29407fec23c305bb"},{"public_id":"co_d1f8638b664e7cea6c7583a45cccd214","status":"active","name":"oxidized cellulose","description":"Cellulose in which the C2 hydroxyl group is oxidized; βGlc(1→4)AF is a mimic of such oxidized cellulose and may undergo analogous decomposition in nature.","types":["compound"],"aliases":[],"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["review"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_d1f8638b664e7cea6c7583a45cccd214"},{"public_id":"co_d39d8a2b6ccda3e6bf9787efb4ecd082","status":"active","name":"temperature","description":"A factor that influences the decomposition rate of βGlc(1→4)AF; higher temperature accelerates decomposition.","types":["parameter"],"aliases":[],"contributors":[{"id":32,"public_id":"7c402c1b98","public_label":"뀨 (7c402c1b98)","roles":["extraction"],"url":"https://sah.borca.ai/u/7c402c1b98"},{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["review"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_d39d8a2b6ccda3e6bf9787efb4ecd082"}],"external_ids":{"DOI":"10.5458/jag.jag.JAG-2017_010","ArXiv":null,"PubMed":34354501,"PubMedCentral":"8056936","MAG":2751153055,"DBLP":null,"ACL":null},"open_access":{"is_open_access":true,"pdf_url":"https://www.jstage.jst.go.jp/article/jag/64/4/64_jag.JAG-2017_010/_pdf","landing_url":"https://www.semanticscholar.org/paper/6226870e7f864ee6acebe398be2ad8029e177672","source":"semantic_scholar","pdf_url_source":"semantic_scholar_open_access_pdf","license":"CCBYNC","status":"GOLD","reason":null},"reference_availability":{"status":"available","references_indexed":true,"full_text_available":false,"full_text_source":null,"count_basis":"semantic_scholar_metadata","extraction_status":"not_applicable","reason":null},"source":{"provider":"episteme2","base_corpus":"semantic_scholar_dump","freshness_mode":"unknown","basis":["semantic_scholar_metadata","postgres_metadata"],"limits":["paper metadata is based on indexed upstream scholarly datasets","claims and concepts are available only for extracted papers","absence of claims or concepts means no extracted graph data is available in this response"],"status":"available","degraded":false,"degraded_reasons":[],"diagnostics":{"status":"available","degraded":false,"degraded_reasons":[],"metadata_status":"available","graph_status":"available","abstract_status":"available"},"source_flags":5},"paper_id":639055,"paper_uid":"bfaf5edf-9897-4dc5-b5a5-4c2a164778e5","canonical_identity":{"paper_id":639055,"paper_uid":"bfaf5edf-9897-4dc5-b5a5-4c2a164778e5","identity_status":"available","lookup_basis":"semantic_scholar_external_id","compatibility_path":"corpus_id"},"url":"https://sah.borca.ai/papers/90151186"}