PubMed:16098956 JSONTXT

{"target":"https://pubannotation.org/docs/sourcedb/PubMed/sourceid/16098956","sourcedb":"PubMed","sourceid":"16098956","source_url":"http://www.ncbi.nlm.nih.gov/pubmed/16098956","text":"Synthesis of some derivatives of C-(1-deoxy-1-N-substituted-D-glucopyranosyl)formic acid (D-gluco-hept-2-ulopyranosonic acid) as potential inhibitors of glycogen phosphorylase.\nPer-O-benzoylated derivatives (amide, methyl ester and glycinamide) of C-(1-azido-1-deoxy-alpha-D-glucopyranosyl)formic acid obtained by azide substitution in the corresponding C-(1-bromo-1-deoxy-beta-D-glucopyranosyl)formic acid derivatives were debenzoylated by the Zemplén-protocol. Per-O-benzoylated C-(1-azido-1-deoxy-alpha-D-glucopyranosyl)formamide was dehydrated by oxalyl chloride-DMF to give the corresponding nitrile, while from its reduction mixture obtained by Raney-nickel or sodium hydrogentelluride C-(1-amino-1-deoxy-beta-D-glucopyranosyl)formamide could be isolated. Acetylation of this amino-amide by Ac2O/Py and subsequent debenzoylation gave C-(1-acetamido-1-deoxy-beta-D-glucopyranosyl)formamide. Applying the same conditions to the crude reduction mixture allowed the alpha-anomer to be isolated as a minor component. An alternative pathway to produce the above beta-anomer appeared in the reaction of C-(1-bromo-1-deoxy-beta-D-glucopyranosyl)formamide with CH3CN in the presence of Ag2CO3 to yield 1-acetamido-2,3,4,6,-tetra-O-benzoyl-1-deoxy-beta-D-glucopyranosyl cyanide, which was hydrated, in the presence of TiCl4, to the formamide. Some of the new compounds were shown to be weak inhibitors of muscle glycogen phosphorylase b.","tracks":[{"project":"Glycosmos6-MAT","denotations":[{"id":"T1","span":{"begin":1401,"end":1407},"obj":"http://purl.obolibrary.org/obo/MAT_0000025"}],"attributes":[{"subj":"T1","pred":"source","obj":"Glycosmos6-MAT"}]},{"project":"sentences","denotations":[{"id":"TextSentencer_T1","span":{"begin":0,"end":176},"obj":"Sentence"},{"id":"TextSentencer_T2","span":{"begin":177,"end":462},"obj":"Sentence"},{"id":"TextSentencer_T3","span":{"begin":463,"end":761},"obj":"Sentence"},{"id":"TextSentencer_T4","span":{"begin":762,"end":895},"obj":"Sentence"},{"id":"TextSentencer_T5","span":{"begin":896,"end":1017},"obj":"Sentence"},{"id":"TextSentencer_T6","span":{"begin":1018,"end":1338},"obj":"Sentence"},{"id":"TextSentencer_T7","span":{"begin":1339,"end":1433},"obj":"Sentence"},{"id":"T1","span":{"begin":0,"end":176},"obj":"Sentence"},{"id":"T2","span":{"begin":177,"end":462},"obj":"Sentence"},{"id":"T3","span":{"begin":463,"end":761},"obj":"Sentence"},{"id":"T4","span":{"begin":762,"end":895},"obj":"Sentence"},{"id":"T5","span":{"begin":896,"end":1017},"obj":"Sentence"},{"id":"T6","span":{"begin":1018,"end":1338},"obj":"Sentence"},{"id":"T7","span":{"begin":1339,"end":1433},"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":"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"}]},{"project":"Anatomy-MAT","denotations":[{"id":"T1","span":{"begin":1401,"end":1407},"obj":"Body_part"}],"attributes":[{"id":"A1","pred":"mat_id","subj":"T1","obj":"http://purl.obolibrary.org/obo/MAT_0000025"},{"subj":"T1","pred":"source","obj":"Anatomy-MAT"}]},{"project":"NCBITAXON","denotations":[{"id":"T1","span":{"begin":177,"end":182},"obj":"OrganismTaxon"},{"id":"T2","span":{"begin":463,"end":468},"obj":"OrganismTaxon"},{"id":"T3","span":{"begin":1220,"end":1227},"obj":"OrganismTaxon"}],"attributes":[{"id":"A1","pred":"db_id","subj":"T1","obj":"214303"},{"id":"A2","pred":"db_id","subj":"T2","obj":"214303"},{"id":"A3","pred":"db_id","subj":"T3","obj":"100829"},{"subj":"T1","pred":"source","obj":"NCBITAXON"},{"subj":"T2","pred":"source","obj":"NCBITAXON"},{"subj":"T3","pred":"source","obj":"NCBITAXON"}]},{"project":"Anatomy-UBERON","denotations":[{"id":"T1","span":{"begin":1401,"end":1407},"obj":"Body_part"}],"attributes":[{"id":"A1","pred":"uberon_id","subj":"T1","obj":"http://purl.obolibrary.org/obo/UBERON_0001630"},{"id":"A2","pred":"uberon_id","subj":"T1","obj":"http://purl.obolibrary.org/obo/UBERON_0005090"},{"subj":"T1","pred":"source","obj":"Anatomy-UBERON"}]}],"config":{"attribute types":[{"pred":"source","value type":"selection","values":[{"id":"Glycosmos6-MAT","color":"#93ecb1","default":true},{"id":"sentences","color":"#ec9793"},{"id":"Anatomy-MAT","color":"#93a8ec"},{"id":"NCBITAXON","color":"#c2ec93"},{"id":"Anatomy-UBERON","color":"#ec93dd"}]}]}}