Enzymatic synthesis of novel oligosaccharides from N-acetylsucrosamine and melibiose using Aspergillus niger α-galactosidase, and properties of the products
Two kinds of oligosaccharides, N-acetylraffinosamine (RafNAc) and N-acetylplanteosamine (PlaNAc), were synthesized from N-acetylsucrosamine and melibiose using the transgalactosylation activity of Aspergillus niger α-galactosidase. RafNAc and PlaNAc are novel trisaccharides in which d-glucopyranose...
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| Veröffentlicht in: | Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2016-09, Vol.80 (9), p.1836-1842 |
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| container_title | Bioscience, biotechnology, and biochemistry |
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| creator | Sakaki, Yohei Tashiro, Mitsuru Katou, Moe Sakuma, Chiseko Hirano, Takako Hakamata, Wataru Nishio, Toshiyuki |
| description | Two kinds of oligosaccharides, N-acetylraffinosamine (RafNAc) and N-acetylplanteosamine (PlaNAc), were synthesized from N-acetylsucrosamine and melibiose using the transgalactosylation activity of Aspergillus niger α-galactosidase. RafNAc and PlaNAc are novel trisaccharides in which d-glucopyranose residues in raffinose (Raf) and planteose are replaced with N-acetyl-d-glucosamine. These trisaccharides were more stable in acidic solution than Raf. RafNAc was hydrolyzed more rapidly than Raf by α-galactosidase of green coffee bean. In contrast, RafNAc was not hydrolyzed by Saccharomyces cerevisiae invertase, although Raf was hydrolyzed well by this enzyme. These results indicate that the physicochemical properties and steric structure of RafNAc differ considerably from those of Raf.
Two kinds of novel trisaccharides were synthesized from N-acetylsucrosamine and melibiose, using transgalactosylation action of Aspergillus niger α-galactosidase. |
| doi_str_mv | 10.1080/09168451.2016.1189316 |
| format | Article |
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Two kinds of novel trisaccharides were synthesized from N-acetylsucrosamine and melibiose, using transgalactosylation action of Aspergillus niger α-galactosidase.</description><identifier>ISSN: 0916-8451</identifier><identifier>EISSN: 1347-6947</identifier><identifier>DOI: 10.1080/09168451.2016.1189316</identifier><identifier>PMID: 27254139</identifier><language>eng</language><publisher>England: Taylor & Francis</publisher><subject>alpha-Galactosidase - genetics ; alpha-Galactosidase - metabolism ; Aspergillus niger - enzymology ; beta-Fructofuranosidase - genetics ; beta-Fructofuranosidase - metabolism ; Hydrolysis ; Melibiose - chemistry ; N-acetylplateosamine ; N-acetylraffinosamine ; oligosaccharide ; Oligosaccharides - biosynthesis ; Oligosaccharides - chemistry ; Raffinose - biosynthesis ; Raffinose - chemistry ; Saccharomyces cerevisiae ; transgalactosylation ; α-galactosidase</subject><ispartof>Bioscience, biotechnology, and biochemistry, 2016-09, Vol.80 (9), p.1836-1842</ispartof><rights>2016 Japan Society for Bioscience, Biotechnology, and Agrochemistry 2016</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3286-bf140deafbfef2e4fcfa2eff2eaafe955d1632b2fbaa6ed44106793d29e1e5b03</citedby><cites>FETCH-LOGICAL-c3286-bf140deafbfef2e4fcfa2eff2eaafe955d1632b2fbaa6ed44106793d29e1e5b03</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27254139$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sakaki, Yohei</creatorcontrib><creatorcontrib>Tashiro, Mitsuru</creatorcontrib><creatorcontrib>Katou, Moe</creatorcontrib><creatorcontrib>Sakuma, Chiseko</creatorcontrib><creatorcontrib>Hirano, Takako</creatorcontrib><creatorcontrib>Hakamata, Wataru</creatorcontrib><creatorcontrib>Nishio, Toshiyuki</creatorcontrib><title>Enzymatic synthesis of novel oligosaccharides from N-acetylsucrosamine and melibiose using Aspergillus niger α-galactosidase, and properties of the products</title><title>Bioscience, biotechnology, and biochemistry</title><addtitle>Biosci Biotechnol Biochem</addtitle><description>Two kinds of oligosaccharides, N-acetylraffinosamine (RafNAc) and N-acetylplanteosamine (PlaNAc), were synthesized from N-acetylsucrosamine and melibiose using the transgalactosylation activity of Aspergillus niger α-galactosidase. RafNAc and PlaNAc are novel trisaccharides in which d-glucopyranose residues in raffinose (Raf) and planteose are replaced with N-acetyl-d-glucosamine. These trisaccharides were more stable in acidic solution than Raf. RafNAc was hydrolyzed more rapidly than Raf by α-galactosidase of green coffee bean. In contrast, RafNAc was not hydrolyzed by Saccharomyces cerevisiae invertase, although Raf was hydrolyzed well by this enzyme. These results indicate that the physicochemical properties and steric structure of RafNAc differ considerably from those of Raf.
Two kinds of novel trisaccharides were synthesized from N-acetylsucrosamine and melibiose, using transgalactosylation action of Aspergillus niger α-galactosidase.</description><subject>alpha-Galactosidase - genetics</subject><subject>alpha-Galactosidase - metabolism</subject><subject>Aspergillus niger - enzymology</subject><subject>beta-Fructofuranosidase - genetics</subject><subject>beta-Fructofuranosidase - metabolism</subject><subject>Hydrolysis</subject><subject>Melibiose - chemistry</subject><subject>N-acetylplateosamine</subject><subject>N-acetylraffinosamine</subject><subject>oligosaccharide</subject><subject>Oligosaccharides - biosynthesis</subject><subject>Oligosaccharides - chemistry</subject><subject>Raffinose - biosynthesis</subject><subject>Raffinose - chemistry</subject><subject>Saccharomyces cerevisiae</subject><subject>transgalactosylation</subject><subject>α-galactosidase</subject><issn>0916-8451</issn><issn>1347-6947</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kUFu1DAUhi0EokPhCCAvWZDBjpNMsqOqSkGqYANr68V-nho59uCXgMJdOAQX4UxNOlOWrGw9f79_Wx9jL6XYStGKt6KTTVvVclsK2WylbDslm0dsI1W1K5qu2j1mm5UpVuiMPSP6JsQyqOVTdlbuyrqSqtuw31fx1zzA6A2nOY63SJ54cjymHxh4Cn6fCIy5hewtEnc5DfxTAQbHOdBk8nI6-IgcouUDBt_7RMgn8nHPL-iAee9DmIhHv8fM__4p9hDAjIm8BcI397lDTgs4erxvXt6wTuxkRnrOnjgIhC9O6zn7-v7qy-WH4ubz9cfLi5vCqLJtit7JSlgE1zt0JVbOOCjRLVsAh11dW9mosi9dD9CgrSopml2nbNmhxLoX6py9Pt67FH-fkEY9eDIYAkRME2nZiq4RlWrVgtZHdP07ZXT6kP0AedZS6NWMfjCjVzP6ZGbJvTpVTP2A9l_qQcUCvDsCPrqUB_iZcrB6hDmk7DJE40mr_3fcAZmBpAc</recordid><startdate>201609</startdate><enddate>201609</enddate><creator>Sakaki, Yohei</creator><creator>Tashiro, Mitsuru</creator><creator>Katou, Moe</creator><creator>Sakuma, Chiseko</creator><creator>Hirano, Takako</creator><creator>Hakamata, Wataru</creator><creator>Nishio, Toshiyuki</creator><general>Taylor & Francis</general><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>201609</creationdate><title>Enzymatic synthesis of novel oligosaccharides from N-acetylsucrosamine and melibiose using Aspergillus niger α-galactosidase, and properties of the products</title><author>Sakaki, Yohei ; Tashiro, Mitsuru ; Katou, Moe ; Sakuma, Chiseko ; Hirano, Takako ; Hakamata, Wataru ; Nishio, Toshiyuki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3286-bf140deafbfef2e4fcfa2eff2eaafe955d1632b2fbaa6ed44106793d29e1e5b03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>alpha-Galactosidase - genetics</topic><topic>alpha-Galactosidase - metabolism</topic><topic>Aspergillus niger - enzymology</topic><topic>beta-Fructofuranosidase - genetics</topic><topic>beta-Fructofuranosidase - metabolism</topic><topic>Hydrolysis</topic><topic>Melibiose - chemistry</topic><topic>N-acetylplateosamine</topic><topic>N-acetylraffinosamine</topic><topic>oligosaccharide</topic><topic>Oligosaccharides - biosynthesis</topic><topic>Oligosaccharides - chemistry</topic><topic>Raffinose - biosynthesis</topic><topic>Raffinose - chemistry</topic><topic>Saccharomyces cerevisiae</topic><topic>transgalactosylation</topic><topic>α-galactosidase</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sakaki, Yohei</creatorcontrib><creatorcontrib>Tashiro, Mitsuru</creatorcontrib><creatorcontrib>Katou, Moe</creatorcontrib><creatorcontrib>Sakuma, Chiseko</creatorcontrib><creatorcontrib>Hirano, Takako</creatorcontrib><creatorcontrib>Hakamata, Wataru</creatorcontrib><creatorcontrib>Nishio, Toshiyuki</creatorcontrib><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>Bioscience, biotechnology, and biochemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sakaki, Yohei</au><au>Tashiro, Mitsuru</au><au>Katou, Moe</au><au>Sakuma, Chiseko</au><au>Hirano, Takako</au><au>Hakamata, Wataru</au><au>Nishio, Toshiyuki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enzymatic synthesis of novel oligosaccharides from N-acetylsucrosamine and melibiose using Aspergillus niger α-galactosidase, and properties of the products</atitle><jtitle>Bioscience, biotechnology, and biochemistry</jtitle><addtitle>Biosci Biotechnol Biochem</addtitle><date>2016-09</date><risdate>2016</risdate><volume>80</volume><issue>9</issue><spage>1836</spage><epage>1842</epage><pages>1836-1842</pages><issn>0916-8451</issn><eissn>1347-6947</eissn><abstract>Two kinds of oligosaccharides, N-acetylraffinosamine (RafNAc) and N-acetylplanteosamine (PlaNAc), were synthesized from N-acetylsucrosamine and melibiose using the transgalactosylation activity of Aspergillus niger α-galactosidase. RafNAc and PlaNAc are novel trisaccharides in which d-glucopyranose residues in raffinose (Raf) and planteose are replaced with N-acetyl-d-glucosamine. These trisaccharides were more stable in acidic solution than Raf. RafNAc was hydrolyzed more rapidly than Raf by α-galactosidase of green coffee bean. In contrast, RafNAc was not hydrolyzed by Saccharomyces cerevisiae invertase, although Raf was hydrolyzed well by this enzyme. These results indicate that the physicochemical properties and steric structure of RafNAc differ considerably from those of Raf.
Two kinds of novel trisaccharides were synthesized from N-acetylsucrosamine and melibiose, using transgalactosylation action of Aspergillus niger α-galactosidase.</abstract><cop>England</cop><pub>Taylor & Francis</pub><pmid>27254139</pmid><doi>10.1080/09168451.2016.1189316</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Bioscience, biotechnology, and biochemistry, 2016-09, Vol.80 (9), p.1836-1842 |
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| source | MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Oxford University Press Journals All Titles (1996-Current); Freely Accessible Japanese Titles |
| subjects | alpha-Galactosidase - genetics alpha-Galactosidase - metabolism Aspergillus niger - enzymology beta-Fructofuranosidase - genetics beta-Fructofuranosidase - metabolism Hydrolysis Melibiose - chemistry N-acetylplateosamine N-acetylraffinosamine oligosaccharide Oligosaccharides - biosynthesis Oligosaccharides - chemistry Raffinose - biosynthesis Raffinose - chemistry Saccharomyces cerevisiae transgalactosylation α-galactosidase |
| title | Enzymatic synthesis of novel oligosaccharides from N-acetylsucrosamine and melibiose using Aspergillus niger α-galactosidase, and properties of the products |
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