PubMed:3063383 JSONTXT

{"target":"https://pubannotation.org/docs/sourcedb/PubMed/sourceid/3063383","sourcedb":"PubMed","sourceid":"3063383","source_url":"http://www.ncbi.nlm.nih.gov/pubmed/3063383","text":"Synthesis and immunoreactivity of neoglycoproteins containing the trisaccharide unit of phenolic glycolipid I of Mycobacterium leprae.\nThe trisaccharide segment, O-(3,6-di-O-methyl-beta-D-glucopyranosyl)-(1----4)-O-(2,3-di-O-methyl- alpha-L-rhamnopyranosyl)-(1----2)-3-O-methyl-L-rhamnopyranose, of the Mycobacterium leprae-specific phenolic glycolipid I has been synthesized as its 8-(methoxycarbonyl)octyl glycoside and coupled to a carrier protein, to produce a leprosy-specific neoglycoprotein, the so-called natural trisaccharide-octyl-bovine serum albumin (NT-O-BSA). Special features of the synthetic strategy were the use of silver trifluoromethanesulfonate (triflate) to promote glycosylation, resulting in the rhamnobiose in high yield and absolute stereospecificity. The terminal 3,6-di-O-methyl-D-glucopyranosyl group was introduced after O-deallylation of the rhamnobiose. Removal of protecting groups yielded the trisaccharide hapten suitable for coupling to carrier protein. Poly(acrylamide)-gel electrophoresis of the neoglycoprotein demonstrated its purity, and subsequent immunoblotting with a monoclonal antibody directed to the terminal 3,6-di-O-methyl-beta-D-glucopyranosyl epitope of the native glycolipid demonstrated its antigenicity. Comparative serological testing in enzyme-linked immunosorbent assays of NT-O-BSA, the corresponding disaccharide-containing products, and another trisaccharide-containing neoglycoprotein, O-(3,6-di-O-methyl-beta-D-glucopyranosyl)-(1----4)-O-(2,3-di-O- methyl-alpha-L-rhamnopyranosyl)-(1----2)-(3-O-methyl-alpha-L-rhamnopy ran osyl)- (1----4')-oxy-(3-phenylpropanoyl)-BSA (NT-P-BSA) [Fujiwara et al., Agric. Biol. Chem., 51 (1987) 2539-2547] against sera from leprosy patients and control populations showed concordance; the presence of the innermost sugar did not contribute significantly to sensitivity or specificity. The di- and tri-saccharide-containing neoantigens, on account of ready availability and solubility, provide greater flexibility than the native glycolipid for the serodiagnosis of leprosy.","tracks":[{"project":"sentences","denotations":[{"id":"TextSentencer_T1","span":{"begin":0,"end":134},"obj":"Sentence"},{"id":"TextSentencer_T2","span":{"begin":135,"end":573},"obj":"Sentence"},{"id":"TextSentencer_T3","span":{"begin":574,"end":777},"obj":"Sentence"},{"id":"TextSentencer_T4","span":{"begin":778,"end":885},"obj":"Sentence"},{"id":"TextSentencer_T5","span":{"begin":886,"end":989},"obj":"Sentence"},{"id":"TextSentencer_T6","span":{"begin":990,"end":1258},"obj":"Sentence"},{"id":"TextSentencer_T7","span":{"begin":1259,"end":1666},"obj":"Sentence"},{"id":"TextSentencer_T8","span":{"begin":1667,"end":1672},"obj":"Sentence"},{"id":"TextSentencer_T9","span":{"begin":1673,"end":1879},"obj":"Sentence"},{"id":"TextSentencer_T10","span":{"begin":1880,"end":2068},"obj":"Sentence"},{"id":"T1","span":{"begin":0,"end":134},"obj":"Sentence"},{"id":"T2","span":{"begin":135,"end":573},"obj":"Sentence"},{"id":"T3","span":{"begin":574,"end":777},"obj":"Sentence"},{"id":"T4","span":{"begin":778,"end":885},"obj":"Sentence"},{"id":"T5","span":{"begin":886,"end":989},"obj":"Sentence"},{"id":"T6","span":{"begin":990,"end":1258},"obj":"Sentence"},{"id":"T7","span":{"begin":1259,"end":1666},"obj":"Sentence"},{"id":"T8","span":{"begin":1667,"end":1672},"obj":"Sentence"},{"id":"T9","span":{"begin":1673,"end":1879},"obj":"Sentence"},{"id":"T10","span":{"begin":1880,"end":2068},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"attributes":[{"subj":"TextSentencer_T1","pred":"source","obj":"sentences"},{"subj":"TextSentencer_T2","pred":"source","obj":"sentences"},{"subj":"TextSentencer_T3","pred":"source","obj":"sentences"},{"subj":"TextSentencer_T4","pred":"source","obj":"sentences"},{"subj":"TextSentencer_T5","pred":"source","obj":"sentences"},{"subj":"TextSentencer_T6","pred":"source","obj":"sentences"},{"subj":"TextSentencer_T7","pred":"source","obj":"sentences"},{"subj":"TextSentencer_T8","pred":"source","obj":"sentences"},{"subj":"TextSentencer_T9","pred":"source","obj":"sentences"},{"subj":"TextSentencer_T10","pred":"source","obj":"sentences"},{"subj":"T1","pred":"source","obj":"sentences"},{"subj":"T2","pred":"source","obj":"sentences"},{"subj":"T3","pred":"source","obj":"sentences"},{"subj":"T4","pred":"source","obj":"sentences"},{"subj":"T5","pred":"source","obj":"sentences"},{"subj":"T6","pred":"source","obj":"sentences"},{"subj":"T7","pred":"source","obj":"sentences"},{"subj":"T8","pred":"source","obj":"sentences"},{"subj":"T9","pred":"source","obj":"sentences"},{"subj":"T10","pred":"source","obj":"sentences"}]},{"project":"NCBITAXON","denotations":[{"id":"T1","span":{"begin":113,"end":133},"obj":"OrganismTaxon"},{"id":"T2","span":{"begin":303,"end":323},"obj":"OrganismTaxon"},{"id":"T3","span":{"begin":541,"end":547},"obj":"OrganismTaxon"}],"attributes":[{"id":"A1","pred":"db_id","subj":"T1","obj":"1769"},{"id":"A2","pred":"db_id","subj":"T2","obj":"1769"},{"id":"A3","pred":"db_id","subj":"T3","obj":"9913"},{"subj":"T1","pred":"source","obj":"NCBITAXON"},{"subj":"T2","pred":"source","obj":"NCBITAXON"},{"subj":"T3","pred":"source","obj":"NCBITAXON"}]},{"project":"mondo_disease","denotations":[{"id":"T1","span":{"begin":465,"end":472},"obj":"Disease"},{"id":"T2","span":{"begin":1719,"end":1726},"obj":"Disease"},{"id":"T3","span":{"begin":2060,"end":2067},"obj":"Disease"}],"attributes":[{"id":"A1","pred":"mondo_id","subj":"T1","obj":"http://purl.obolibrary.org/obo/MONDO_0005124"},{"id":"A2","pred":"mondo_id","subj":"T2","obj":"http://purl.obolibrary.org/obo/MONDO_0005124"},{"id":"A3","pred":"mondo_id","subj":"T3","obj":"http://purl.obolibrary.org/obo/MONDO_0005124"},{"subj":"T1","pred":"source","obj":"mondo_disease"},{"subj":"T2","pred":"source","obj":"mondo_disease"},{"subj":"T3","pred":"source","obj":"mondo_disease"}]},{"project":"Anatomy-UBERON","denotations":[{"id":"T1","span":{"begin":153,"end":160},"obj":"Body_part"}],"attributes":[{"id":"A1","pred":"uberon_id","subj":"T1","obj":"http://purl.obolibrary.org/obo/UBERON_0000914"},{"subj":"T1","pred":"source","obj":"Anatomy-UBERON"}]},{"project":"CL-cell","denotations":[{"id":"T1","span":{"begin":990,"end":994},"obj":"Cell"}],"attributes":[{"id":"A1","pred":"cl_id","subj":"T1","obj":"http://purl.obolibrary.org/obo/CL:0000096"},{"id":"A2","pred":"cl_id","subj":"T1","obj":"http://purl.obolibrary.org/obo/CL:0000775"},{"subj":"T1","pred":"source","obj":"CL-cell"}]}],"config":{"attribute types":[{"pred":"source","value type":"selection","values":[{"id":"sentences","color":"#93ece3","default":true},{"id":"NCBITAXON","color":"#ecc993"},{"id":"mondo_disease","color":"#af93ec"},{"id":"Anatomy-UBERON","color":"#93ec95"},{"id":"CL-cell","color":"#ec93aa"}]}]}}