Synthesis of New N-Containing Maltooligosaccharides, α-Amylase Inhibitors, and Their Biological Activities
Fifteen new N-containing maltooligosaccharides were obtained using the chemoenzymatic method. Among these compounds, maltooligosaccharides having 6-amino-6-deoxy-D-sorbitol residue, (3R, 4R, 5R, 6S)-hexahydro-3, 4, 5, 6-tetrahydroxy-1H-azepine residue, and (3R, 5R)-3, 4, 5-trihydroxypiperidine resid...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1999/02/15, Vol.47(2), pp.187-193 |
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| creator | UCHIDA, Riichiro NASU, Ayako TOKUTAKE, Shoichi KASAI, Kouichi TOBE, Koichiro YAMAJI, Nobuyuki |
| description | Fifteen new N-containing maltooligosaccharides were obtained using the chemoenzymatic method. Among these compounds, maltooligosaccharides having 6-amino-6-deoxy-D-sorbitol residue, (3R, 4R, 5R, 6S)-hexahydro-3, 4, 5, 6-tetrahydroxy-1H-azepine residue, and (3R, 5R)-3, 4, 5-trihydroxypiperidine residue at the reducing end showed strong inhibitory activities for human pancreatic α-amylase (HPA) (EC 3.2.1.1) and human salivary α-amylase (HSA). The administration of (3R, 4R, 5R, 6S)-hexahydro-3, 5, 6-trihydroxy-1H-azepine-4-yl O-α-D-glucopyranosyl-(1→4)-α-D-glucopyranoside (13, IC50=4.3×10-5M for HPA, IC50=8.2×10-5M for HSA) and (3R, 5R)-3, 5-dihydroxypiperidine-4-yl O-α-D-glucopyranosyl-(1→4)-α-D-glucopyranoside (18, IC50=3.4×10-5M for HPA, IC50=4.6×10-5M for HSA) to ICR mice suppressed postprandial hyperglycemia. |
| doi_str_mv | 10.1248/cpb.47.187 |
| format | Article |
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Among these compounds, maltooligosaccharides having 6-amino-6-deoxy-D-sorbitol residue, (3R, 4R, 5R, 6S)-hexahydro-3, 4, 5, 6-tetrahydroxy-1H-azepine residue, and (3R, 5R)-3, 4, 5-trihydroxypiperidine residue at the reducing end showed strong inhibitory activities for human pancreatic α-amylase (HPA) (EC 3.2.1.1) and human salivary α-amylase (HSA). The administration of (3R, 4R, 5R, 6S)-hexahydro-3, 5, 6-trihydroxy-1H-azepine-4-yl O-α-D-glucopyranosyl-(1→4)-α-D-glucopyranoside (13, IC50=4.3×10-5M for HPA, IC50=8.2×10-5M for HSA) and (3R, 5R)-3, 5-dihydroxypiperidine-4-yl O-α-D-glucopyranosyl-(1→4)-α-D-glucopyranoside (18, IC50=3.4×10-5M for HPA, IC50=4.6×10-5M for HSA) to ICR mice suppressed postprandial hyperglycemia.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.47.187</identifier><identifier>PMID: 10071853</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>alpha-Amylases - antagonists & inhibitors ; Animals ; Azepines - chemical synthesis ; Azepines - pharmacology ; Biological and medical sciences ; Blood Glucose - metabolism ; Carbohydrate Sequence ; chemoenzymatic synthesis ; Disaccharides - chemical synthesis ; Disaccharides - pharmacology ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - pharmacology ; General and cellular metabolism. Vitamins ; Glycoside Hydrolase Inhibitors ; Humans ; Hyperglycemia - drug therapy ; Hypoglycemic Agents - chemical synthesis ; Hypoglycemic Agents - pharmacology ; inhibitor ; Intestine, Small - enzymology ; Magnetic Resonance Spectroscopy ; Male ; Medical sciences ; Mice ; Mice, Inbred ICR ; Molecular Sequence Data ; Pancreas - enzymology ; Pharmacology. Drug treatments ; Piperidines - chemical synthesis ; Piperidines - pharmacology ; postprandial hyperglycemia ; Postprandial Period ; Rats ; Salivary Glands - enzymology ; α-amylase</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1999/02/15, Vol.47(2), pp.187-193</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1999 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c474t-5eb64145907f981d79044c75f7f82607bd653830a71e68c3eb0341ec489a91c93</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1783556$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10071853$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>UCHIDA, Riichiro</creatorcontrib><creatorcontrib>NASU, Ayako</creatorcontrib><creatorcontrib>TOKUTAKE, Shoichi</creatorcontrib><creatorcontrib>KASAI, Kouichi</creatorcontrib><creatorcontrib>TOBE, Koichiro</creatorcontrib><creatorcontrib>YAMAJI, Nobuyuki</creatorcontrib><title>Synthesis of New N-Containing Maltooligosaccharides, α-Amylase Inhibitors, and Their Biological Activities</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Fifteen new N-containing maltooligosaccharides were obtained using the chemoenzymatic method. Among these compounds, maltooligosaccharides having 6-amino-6-deoxy-D-sorbitol residue, (3R, 4R, 5R, 6S)-hexahydro-3, 4, 5, 6-tetrahydroxy-1H-azepine residue, and (3R, 5R)-3, 4, 5-trihydroxypiperidine residue at the reducing end showed strong inhibitory activities for human pancreatic α-amylase (HPA) (EC 3.2.1.1) and human salivary α-amylase (HSA). The administration of (3R, 4R, 5R, 6S)-hexahydro-3, 5, 6-trihydroxy-1H-azepine-4-yl O-α-D-glucopyranosyl-(1→4)-α-D-glucopyranoside (13, IC50=4.3×10-5M for HPA, IC50=8.2×10-5M for HSA) and (3R, 5R)-3, 5-dihydroxypiperidine-4-yl O-α-D-glucopyranosyl-(1→4)-α-D-glucopyranoside (18, IC50=3.4×10-5M for HPA, IC50=4.6×10-5M for HSA) to ICR mice suppressed postprandial hyperglycemia.</description><subject>alpha-Amylases - antagonists & inhibitors</subject><subject>Animals</subject><subject>Azepines - chemical synthesis</subject><subject>Azepines - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Blood Glucose - metabolism</subject><subject>Carbohydrate Sequence</subject><subject>chemoenzymatic synthesis</subject><subject>Disaccharides - chemical synthesis</subject><subject>Disaccharides - pharmacology</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>General and cellular metabolism. Vitamins</subject><subject>Glycoside Hydrolase Inhibitors</subject><subject>Humans</subject><subject>Hyperglycemia - drug therapy</subject><subject>Hypoglycemic Agents - chemical synthesis</subject><subject>Hypoglycemic Agents - pharmacology</subject><subject>inhibitor</subject><subject>Intestine, Small - enzymology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Mice, Inbred ICR</subject><subject>Molecular Sequence Data</subject><subject>Pancreas - enzymology</subject><subject>Pharmacology. Drug treatments</subject><subject>Piperidines - chemical synthesis</subject><subject>Piperidines - pharmacology</subject><subject>postprandial hyperglycemia</subject><subject>Postprandial Period</subject><subject>Rats</subject><subject>Salivary Glands - enzymology</subject><subject>α-amylase</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpNkU2OEzEQhS0EYsLAhgOgXiAWiA52227byxDxM9IwLBjWlttdnXhw7GA7oByLi3AmHHXEsKmS6n2qp3qF0HOCl6Rj8q3dD0smlkSKB2hBKBMt7zr6EC0wxqrtaE8v0JOc7zDuOBb0MbogGAsiOV2g71-PoWwhu9zEqbmBX81Nu46hGBdc2DSfjS8xereJ2Vi7NcmNkN80f363q93RmwzNVdi6wZWY6tiEsbndgkvNOxd93DhrfLOyxf10xUF-ih5Nxmd4du6X6NuH97frT-31l49X69V1a5lgpeUw9IwwrrCYlCSjUJgxK_gkJtn1WAxjz6mk2AgCvbQUBkwZAcukMopYRS_Rq3nvPsUfB8hF71y24L0JEA9Z96ongjFRwdczaFPMOcGk98ntTDpqgvUpWl2j1UzoGm2FX5y3HoYdjP-hc5YVeHkGTK6HT8kE6_I9JyTlvK_YesbucjEb-KebVJz1cLIkisuTbTeX6n6v1h9oCPQv6A-ZQg</recordid><startdate>19990201</startdate><enddate>19990201</enddate><creator>UCHIDA, Riichiro</creator><creator>NASU, Ayako</creator><creator>TOKUTAKE, Shoichi</creator><creator>KASAI, Kouichi</creator><creator>TOBE, Koichiro</creator><creator>YAMAJI, Nobuyuki</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>19990201</creationdate><title>Synthesis of New N-Containing Maltooligosaccharides, α-Amylase Inhibitors, and Their Biological Activities</title><author>UCHIDA, Riichiro ; NASU, Ayako ; TOKUTAKE, Shoichi ; KASAI, Kouichi ; TOBE, Koichiro ; YAMAJI, Nobuyuki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c474t-5eb64145907f981d79044c75f7f82607bd653830a71e68c3eb0341ec489a91c93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>alpha-Amylases - antagonists & inhibitors</topic><topic>Animals</topic><topic>Azepines - chemical synthesis</topic><topic>Azepines - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Blood Glucose - metabolism</topic><topic>Carbohydrate Sequence</topic><topic>chemoenzymatic synthesis</topic><topic>Disaccharides - chemical synthesis</topic><topic>Disaccharides - pharmacology</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>General and cellular metabolism. Vitamins</topic><topic>Glycoside Hydrolase Inhibitors</topic><topic>Humans</topic><topic>Hyperglycemia - drug therapy</topic><topic>Hypoglycemic Agents - chemical synthesis</topic><topic>Hypoglycemic Agents - pharmacology</topic><topic>inhibitor</topic><topic>Intestine, Small - enzymology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Mice, Inbred ICR</topic><topic>Molecular Sequence Data</topic><topic>Pancreas - enzymology</topic><topic>Pharmacology. Drug treatments</topic><topic>Piperidines - chemical synthesis</topic><topic>Piperidines - pharmacology</topic><topic>postprandial hyperglycemia</topic><topic>Postprandial Period</topic><topic>Rats</topic><topic>Salivary Glands - enzymology</topic><topic>α-amylase</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>UCHIDA, Riichiro</creatorcontrib><creatorcontrib>NASU, Ayako</creatorcontrib><creatorcontrib>TOKUTAKE, Shoichi</creatorcontrib><creatorcontrib>KASAI, Kouichi</creatorcontrib><creatorcontrib>TOBE, Koichiro</creatorcontrib><creatorcontrib>YAMAJI, Nobuyuki</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>UCHIDA, Riichiro</au><au>NASU, Ayako</au><au>TOKUTAKE, Shoichi</au><au>KASAI, Kouichi</au><au>TOBE, Koichiro</au><au>YAMAJI, Nobuyuki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of New N-Containing Maltooligosaccharides, α-Amylase Inhibitors, and Their Biological Activities</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1999-02-01</date><risdate>1999</risdate><volume>47</volume><issue>2</issue><spage>187</spage><epage>193</epage><pages>187-193</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>Fifteen new N-containing maltooligosaccharides were obtained using the chemoenzymatic method. Among these compounds, maltooligosaccharides having 6-amino-6-deoxy-D-sorbitol residue, (3R, 4R, 5R, 6S)-hexahydro-3, 4, 5, 6-tetrahydroxy-1H-azepine residue, and (3R, 5R)-3, 4, 5-trihydroxypiperidine residue at the reducing end showed strong inhibitory activities for human pancreatic α-amylase (HPA) (EC 3.2.1.1) and human salivary α-amylase (HSA). The administration of (3R, 4R, 5R, 6S)-hexahydro-3, 5, 6-trihydroxy-1H-azepine-4-yl O-α-D-glucopyranosyl-(1→4)-α-D-glucopyranoside (13, IC50=4.3×10-5M for HPA, IC50=8.2×10-5M for HSA) and (3R, 5R)-3, 5-dihydroxypiperidine-4-yl O-α-D-glucopyranosyl-(1→4)-α-D-glucopyranoside (18, IC50=3.4×10-5M for HPA, IC50=4.6×10-5M for HSA) to ICR mice suppressed postprandial hyperglycemia.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>10071853</pmid><doi>10.1248/cpb.47.187</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | alpha-Amylases - antagonists & inhibitors Animals Azepines - chemical synthesis Azepines - pharmacology Biological and medical sciences Blood Glucose - metabolism Carbohydrate Sequence chemoenzymatic synthesis Disaccharides - chemical synthesis Disaccharides - pharmacology Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - pharmacology General and cellular metabolism. Vitamins Glycoside Hydrolase Inhibitors Humans Hyperglycemia - drug therapy Hypoglycemic Agents - chemical synthesis Hypoglycemic Agents - pharmacology inhibitor Intestine, Small - enzymology Magnetic Resonance Spectroscopy Male Medical sciences Mice Mice, Inbred ICR Molecular Sequence Data Pancreas - enzymology Pharmacology. Drug treatments Piperidines - chemical synthesis Piperidines - pharmacology postprandial hyperglycemia Postprandial Period Rats Salivary Glands - enzymology α-amylase |
| title | Synthesis of New N-Containing Maltooligosaccharides, α-Amylase Inhibitors, and Their Biological Activities |
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