PubMed:2524254 JSONTXT

{"project":"sentences","denotations":[{"id":"TextSentencer_T1","span":{"begin":0,"end":188},"obj":"Sentence"},{"id":"TextSentencer_T2","span":{"begin":189,"end":285},"obj":"Sentence"},{"id":"TextSentencer_T3","span":{"begin":286,"end":418},"obj":"Sentence"},{"id":"TextSentencer_T4","span":{"begin":419,"end":644},"obj":"Sentence"},{"id":"TextSentencer_T5","span":{"begin":645,"end":732},"obj":"Sentence"},{"id":"TextSentencer_T6","span":{"begin":733,"end":971},"obj":"Sentence"},{"id":"TextSentencer_T7","span":{"begin":972,"end":1269},"obj":"Sentence"},{"id":"TextSentencer_T8","span":{"begin":1270,"end":1473},"obj":"Sentence"},{"id":"TextSentencer_T9","span":{"begin":1474,"end":1640},"obj":"Sentence"},{"id":"TextSentencer_T10","span":{"begin":1641,"end":1764},"obj":"Sentence"},{"id":"TextSentencer_T11","span":{"begin":1765,"end":1936},"obj":"Sentence"},{"id":"T1","span":{"begin":0,"end":188},"obj":"Sentence"},{"id":"T2","span":{"begin":189,"end":285},"obj":"Sentence"},{"id":"T3","span":{"begin":286,"end":418},"obj":"Sentence"},{"id":"T4","span":{"begin":419,"end":644},"obj":"Sentence"},{"id":"T5","span":{"begin":645,"end":732},"obj":"Sentence"},{"id":"T6","span":{"begin":733,"end":971},"obj":"Sentence"},{"id":"T7","span":{"begin":972,"end":1269},"obj":"Sentence"},{"id":"T8","span":{"begin":1270,"end":1473},"obj":"Sentence"},{"id":"T9","span":{"begin":1474,"end":1640},"obj":"Sentence"},{"id":"T10","span":{"begin":1641,"end":1764},"obj":"Sentence"},{"id":"T11","span":{"begin":1765,"end":1936},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"Synthesis of 4,6-dideoxysucrose, and inhibition studies of Leuconostoc and Streptococcus D-glucansucrases with deoxy and chloro derivatives of sucrose modified at carbon atoms 3, 4, and 6.\nStarting from sucrose, 2,3,1',3',4',6'-hexa-O-benzoyl-6-deoxy-6-iodosucrose (1) was synthesized. Reaction of 1 with sulfuryl chloride in pyridine gave 2,3,1',3',4',6'-hexa-O-benzoyl-4-chloro-4,6-dideoxy-6-iodogalactosucr ose (2). Compound 2 was treated with tributyltin hydride in toluene in the presence of a radical initiator, alpha, alpha-azobis(isobutanonitrile) (AIBN), to remove iodine and chlorine groups and give hexa-O-benzoyl-4,6-dideoxysucrose. Benzoyl groups were removed by sodium methoxide in methanol to give 4,6-dideoxysucrose. Sucrose was modified at carbon atom 3, carbon atom 4, or carbon atoms 4 and 6, and these analogs were tested as inhibitors of the D-glucansucrases (D-glucosyltransferases) of Streptococcus mutans 6715 and Leuconostoc mesenteroides B-512F. Sucrose analogs used in this study are 4-deoxysucrose and 4-chloro-4-deoxygalactosucrose with S. mutans 6715 D-glucansucrases (GTF-S and GTF-I), and 3-deoxysucrose, 4-deoxysucrose, 4-chloro-4-deoxygalactosucrose, 6-deoxysucrose, and 4,6-dideoxysucrose with L. mesenteroides B-512F D-glucansucrase. The data indicate that 3-deoxysucrose, 4-deoxysucrose, and 4-chloro-4-deoxygalactosucrose are weak noncompetitive inhibitors for B-512F dextransucrase, with Ki values of 530, 201, and 202mM respectively. For the same enzyme, 6-deoxysucrose was a strong competitive inhibitor, with Ki of 1.60mM, and 4,6-dideoxysucrose was a good competitive inhibitor, with Ki of 20.3mM. 4-Deoxysucrose was a weak noncompetitive inhibitor for both GTF-I and GTF-S, with Ki values of 672 and 608mM, respectively. 4-Chloro-4-deoxygalactosucrose was also a weak noncompetitive inhibitor for GTF-I and GTF-S with Ki values of 391 and 308mM, respectively.(ABSTRACT TRUNCATED AT 250 WORDS)"}

{"project":"NCBITAXON","denotations":[{"id":"T1","span":{"begin":59,"end":70},"obj":"OrganismTaxon"},{"id":"T2","span":{"begin":75,"end":88},"obj":"OrganismTaxon"},{"id":"T3","span":{"begin":908,"end":928},"obj":"OrganismTaxon"},{"id":"T4","span":{"begin":938,"end":963},"obj":"OrganismTaxon"}],"attributes":[{"id":"A1","pred":"db_id","subj":"T1","obj":"1243"},{"id":"A2","pred":"db_id","subj":"T2","obj":"1301"},{"id":"A3","pred":"db_id","subj":"T3","obj":"1309"},{"id":"A4","pred":"db_id","subj":"T4","obj":"1245"}],"text":"Synthesis of 4,6-dideoxysucrose, and inhibition studies of Leuconostoc and Streptococcus D-glucansucrases with deoxy and chloro derivatives of sucrose modified at carbon atoms 3, 4, and 6.\nStarting from sucrose, 2,3,1',3',4',6'-hexa-O-benzoyl-6-deoxy-6-iodosucrose (1) was synthesized. Reaction of 1 with sulfuryl chloride in pyridine gave 2,3,1',3',4',6'-hexa-O-benzoyl-4-chloro-4,6-dideoxy-6-iodogalactosucr ose (2). Compound 2 was treated with tributyltin hydride in toluene in the presence of a radical initiator, alpha, alpha-azobis(isobutanonitrile) (AIBN), to remove iodine and chlorine groups and give hexa-O-benzoyl-4,6-dideoxysucrose. Benzoyl groups were removed by sodium methoxide in methanol to give 4,6-dideoxysucrose. Sucrose was modified at carbon atom 3, carbon atom 4, or carbon atoms 4 and 6, and these analogs were tested as inhibitors of the D-glucansucrases (D-glucosyltransferases) of Streptococcus mutans 6715 and Leuconostoc mesenteroides B-512F. Sucrose analogs used in this study are 4-deoxysucrose and 4-chloro-4-deoxygalactosucrose with S. mutans 6715 D-glucansucrases (GTF-S and GTF-I), and 3-deoxysucrose, 4-deoxysucrose, 4-chloro-4-deoxygalactosucrose, 6-deoxysucrose, and 4,6-dideoxysucrose with L. mesenteroides B-512F D-glucansucrase. The data indicate that 3-deoxysucrose, 4-deoxysucrose, and 4-chloro-4-deoxygalactosucrose are weak noncompetitive inhibitors for B-512F dextransucrase, with Ki values of 530, 201, and 202mM respectively. For the same enzyme, 6-deoxysucrose was a strong competitive inhibitor, with Ki of 1.60mM, and 4,6-dideoxysucrose was a good competitive inhibitor, with Ki of 20.3mM. 4-Deoxysucrose was a weak noncompetitive inhibitor for both GTF-I and GTF-S, with Ki values of 672 and 608mM, respectively. 4-Chloro-4-deoxygalactosucrose was also a weak noncompetitive inhibitor for GTF-I and GTF-S with Ki values of 391 and 308mM, respectively.(ABSTRACT TRUNCATED AT 250 WORDS)"}