PubMed:12007470 JSONTXT

{"target":"https://pubannotation.org/docs/sourcedb/PubMed/sourceid/12007470","sourcedb":"PubMed","sourceid":"12007470","source_url":"http://www.ncbi.nlm.nih.gov/pubmed/12007470","text":"1,5-Anhydro-D-fructose; a versatile chiral building block: biochemistry and chemistry.\nThere is a steadily increasing need to expand sustainable resources, and carbohydrates are anticipated to play an important role in this respect, both for bulk and fine chemical preparation. The enzyme alpha-(1--\u003e4)-glucan lyase degrades starch to 1,5-anhydro-D-fructose. This compound, which has three different functional properties, a prochiral center together with a permanent pyran ring, renders it a potential chiral building block for the synthesis of valuable and potentially biologically active compounds. 1,5-Anhydro-D-fructose is found in natural materials as a degradation product of alpha-(1--\u003e4)-glucans. The occurrence of lyases and the metabolism of 1,5-anhydro-D-fructose are reviewed in the biological part of this article. In the chemical part, the elucidated structure of 1,5-anhydro-D-fructose will be presented together with simple stereoselective conversions into hydroxy/amino 1,5-anhydro hexitols and a nojirimycin analogue. Synthesis of 6-O-acylated derivatives of 1,5-anhydro-D-fructose substituted with long fatty acid residues is carried out using commercially available enzymes. Those reactions lead to compounds with potential emulsifying properties. The use of protected derivatives of 1,5-anhydro-D-fructose for the synthesis of natural products is likewise reviewed. The potential utilization of this chemical building block is far from being exhausted. Since 1,5-anhydro-D-fructose now is accessible in larger amounts through a simple-enzyme catalyzed degradation of starch by alpha-(1--\u003e4)-glucan lyase, the application of 1,5-anhydro-D-fructose may be considered a valuable contribution to the utilization of carbohydrates as the most abundant resource of sustainable raw materials.","tracks":[{"project":"sentences","denotations":[{"id":"TextSentencer_T1","span":{"begin":0,"end":86},"obj":"Sentence"},{"id":"TextSentencer_T2","span":{"begin":87,"end":277},"obj":"Sentence"},{"id":"TextSentencer_T3","span":{"begin":278,"end":358},"obj":"Sentence"},{"id":"TextSentencer_T4","span":{"begin":359,"end":601},"obj":"Sentence"},{"id":"TextSentencer_T5","span":{"begin":602,"end":705},"obj":"Sentence"},{"id":"TextSentencer_T6","span":{"begin":706,"end":828},"obj":"Sentence"},{"id":"TextSentencer_T7","span":{"begin":829,"end":1036},"obj":"Sentence"},{"id":"TextSentencer_T8","span":{"begin":1037,"end":1195},"obj":"Sentence"},{"id":"TextSentencer_T9","span":{"begin":1196,"end":1268},"obj":"Sentence"},{"id":"TextSentencer_T10","span":{"begin":1269,"end":1387},"obj":"Sentence"},{"id":"TextSentencer_T11","span":{"begin":1388,"end":1474},"obj":"Sentence"},{"id":"TextSentencer_T12","span":{"begin":1475,"end":1806},"obj":"Sentence"},{"id":"T1","span":{"begin":0,"end":86},"obj":"Sentence"},{"id":"T2","span":{"begin":87,"end":277},"obj":"Sentence"},{"id":"T3","span":{"begin":278,"end":358},"obj":"Sentence"},{"id":"T4","span":{"begin":359,"end":601},"obj":"Sentence"},{"id":"T5","span":{"begin":602,"end":705},"obj":"Sentence"},{"id":"T6","span":{"begin":706,"end":828},"obj":"Sentence"},{"id":"T7","span":{"begin":829,"end":1036},"obj":"Sentence"},{"id":"T8","span":{"begin":1037,"end":1195},"obj":"Sentence"},{"id":"T9","span":{"begin":1196,"end":1268},"obj":"Sentence"},{"id":"T10","span":{"begin":1269,"end":1387},"obj":"Sentence"},{"id":"T11","span":{"begin":1388,"end":1474},"obj":"Sentence"},{"id":"T12","span":{"begin":1475,"end":1806},"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":"TextSentencer_T11","pred":"source","obj":"sentences"},{"subj":"TextSentencer_T12","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"},{"subj":"T11","pred":"source","obj":"sentences"},{"subj":"T12","pred":"source","obj":"sentences"}]}],"config":{"attribute types":[{"pred":"source","value type":"selection","values":[{"id":"sentences","color":"#ecd393","default":true}]}]}}