Complete structure of the polysaccharide from Streptococcus sanguis J22
The cell wall polysaccharides of certain oral streptococci such as Streptococcus sanguis strains 34 and J22, although immunologically distinct, act as receptors for the fimbrial lectins of Actinomyces viscosus T14V. We report the complete covalent structure of the polysaccharide from S. sanguis J22...
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| Veröffentlicht in: | Biochemistry (Easton) 1990-01, Vol.29 (1), p.234-248 |
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| creator | Abeygunawardana, Chitrananda Bush, C. Allen Cisar, John O |
| description | The cell wall polysaccharides of certain oral streptococci such as Streptococcus sanguis strains 34 and J22, although immunologically distinct, act as receptors for the fimbrial lectins of Actinomyces viscosus T14V. We report the complete covalent structure of the polysaccharide from S. sanguis J22 which is composed of a heptasaccharide subunit linked by phosphodiester bonds. The repeating subunit, which contains alpha-GalNAc, alpha-rhamnose, beta-rhamnose, beta-glucose, and beta-galactose all in the pyranoside form and beta-galactofuranose, is compared with the previously published structure of the polysaccharide from strain 34. The structure has been determined almost exclusively by high-resolution nuclear magnetic resonance methods. The 1H and 13C NMR spectra of the polysaccharides from both strains 34 and J22 have been completely assigned. The stereochemistry of pyranosides was assigned from JH-H values determined from phase-sensitive COSY spectra, and acetamido sugars were assigned by correlation of the resonances of the amide 1H with the sugar ring protons. The 13C spectra were assigned by 1H-detected multiple-quantum correlation (HMQC) spectra, and the assignments were confirmed by 1H-detected multiple-bond correlation (HMBC) spectra. The positions of the glycosidic linkages were assigned by detection of three-bond 1H-13C correlation across the glycosidic linkage in the HMBC spectra. The positions of the phosphodiester linkages were determined by splittings observed in the 13C resonances due to 31P coupling and also by 1H-detected 31P correlation spectroscopy. |
| doi_str_mv | 10.1021/bi00453a032 |
| format | Article |
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Allen ; Cisar, John O</creator><creatorcontrib>Abeygunawardana, Chitrananda ; Bush, C. Allen ; Cisar, John O</creatorcontrib><description>The cell wall polysaccharides of certain oral streptococci such as Streptococcus sanguis strains 34 and J22, although immunologically distinct, act as receptors for the fimbrial lectins of Actinomyces viscosus T14V. We report the complete covalent structure of the polysaccharide from S. sanguis J22 which is composed of a heptasaccharide subunit linked by phosphodiester bonds. The repeating subunit, which contains alpha-GalNAc, alpha-rhamnose, beta-rhamnose, beta-glucose, and beta-galactose all in the pyranoside form and beta-galactofuranose, is compared with the previously published structure of the polysaccharide from strain 34. The structure has been determined almost exclusively by high-resolution nuclear magnetic resonance methods. The 1H and 13C NMR spectra of the polysaccharides from both strains 34 and J22 have been completely assigned. The stereochemistry of pyranosides was assigned from JH-H values determined from phase-sensitive COSY spectra, and acetamido sugars were assigned by correlation of the resonances of the amide 1H with the sugar ring protons. The 13C spectra were assigned by 1H-detected multiple-quantum correlation (HMQC) spectra, and the assignments were confirmed by 1H-detected multiple-bond correlation (HMBC) spectra. The positions of the glycosidic linkages were assigned by detection of three-bond 1H-13C correlation across the glycosidic linkage in the HMBC spectra. The positions of the phosphodiester linkages were determined by splittings observed in the 13C resonances due to 31P coupling and also by 1H-detected 31P correlation spectroscopy.</description><identifier>ISSN: 0006-2960</identifier><identifier>EISSN: 1520-4995</identifier><identifier>DOI: 10.1021/bi00453a032</identifier><identifier>PMID: 2157479</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>550601 - Medicine- Unsealed Radionuclides in Diagnostics ; BACTERIA ; BARYONS ; Biological and medical sciences ; Carbohydrate Conformation ; CARBOHYDRATES ; CARBON 13 ; CARBON ISOTOPES ; CELL CONSTITUENTS ; Cell receptors ; Cell structures and functions ; CELL WALL ; Cell Wall - ultrastructure ; CHEMICAL BONDS ; ELEMENTARY PARTICLES ; EVEN-ODD NUCLEI ; FERMIONS ; Fundamental and applied biological sciences. Psychology ; HADRONS ; ISOTOPES ; LIGHT NUCLEI ; MAGNETIC RESONANCE ; Magnetic Resonance Spectroscopy - methods ; MEMBRANE PROTEINS ; MICROORGANISMS ; Molecular and cellular biology ; MOLECULAR STRUCTURE ; NUCLEAR MAGNETIC RESONANCE ; NUCLEI ; NUCLEONS ; ODD-EVEN NUCLEI ; ORGANIC COMPOUNDS ; Phosphorus ; PHOSPHORUS 31 ; PHOSPHORUS ISOTOPES ; POLYSACCHARIDES ; Polysaccharides, Bacterial ; PROTEINS ; PROTONS ; RADIOLOGY AND NUCLEAR MEDICINE ; RECEPTORS ; RESONANCE ; SACCHARIDES ; STABLE ISOTOPES ; STEREOCHEMISTRY ; STREPTOCOCCUS ; Streptococcus sanguis</subject><ispartof>Biochemistry (Easton), 1990-01, Vol.29 (1), p.234-248</ispartof><rights>1990 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a410t-54fa55ec434bc6c72cd1ef0f158692b21884e3fb2a20861b481b81cc587d77c83</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/bi00453a032$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/bi00453a032$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,776,780,881,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=6694453$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/2157479$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/7009273$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Abeygunawardana, Chitrananda</creatorcontrib><creatorcontrib>Bush, C. Allen</creatorcontrib><creatorcontrib>Cisar, John O</creatorcontrib><title>Complete structure of the polysaccharide from Streptococcus sanguis J22</title><title>Biochemistry (Easton)</title><addtitle>Biochemistry</addtitle><description>The cell wall polysaccharides of certain oral streptococci such as Streptococcus sanguis strains 34 and J22, although immunologically distinct, act as receptors for the fimbrial lectins of Actinomyces viscosus T14V. We report the complete covalent structure of the polysaccharide from S. sanguis J22 which is composed of a heptasaccharide subunit linked by phosphodiester bonds. The repeating subunit, which contains alpha-GalNAc, alpha-rhamnose, beta-rhamnose, beta-glucose, and beta-galactose all in the pyranoside form and beta-galactofuranose, is compared with the previously published structure of the polysaccharide from strain 34. The structure has been determined almost exclusively by high-resolution nuclear magnetic resonance methods. The 1H and 13C NMR spectra of the polysaccharides from both strains 34 and J22 have been completely assigned. The stereochemistry of pyranosides was assigned from JH-H values determined from phase-sensitive COSY spectra, and acetamido sugars were assigned by correlation of the resonances of the amide 1H with the sugar ring protons. The 13C spectra were assigned by 1H-detected multiple-quantum correlation (HMQC) spectra, and the assignments were confirmed by 1H-detected multiple-bond correlation (HMBC) spectra. The positions of the glycosidic linkages were assigned by detection of three-bond 1H-13C correlation across the glycosidic linkage in the HMBC spectra. The positions of the phosphodiester linkages were determined by splittings observed in the 13C resonances due to 31P coupling and also by 1H-detected 31P correlation spectroscopy.</description><subject>550601 - Medicine- Unsealed Radionuclides in Diagnostics</subject><subject>BACTERIA</subject><subject>BARYONS</subject><subject>Biological and medical sciences</subject><subject>Carbohydrate Conformation</subject><subject>CARBOHYDRATES</subject><subject>CARBON 13</subject><subject>CARBON ISOTOPES</subject><subject>CELL CONSTITUENTS</subject><subject>Cell receptors</subject><subject>Cell structures and functions</subject><subject>CELL WALL</subject><subject>Cell Wall - ultrastructure</subject><subject>CHEMICAL BONDS</subject><subject>ELEMENTARY PARTICLES</subject><subject>EVEN-ODD NUCLEI</subject><subject>FERMIONS</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>HADRONS</subject><subject>ISOTOPES</subject><subject>LIGHT NUCLEI</subject><subject>MAGNETIC RESONANCE</subject><subject>Magnetic Resonance Spectroscopy - methods</subject><subject>MEMBRANE PROTEINS</subject><subject>MICROORGANISMS</subject><subject>Molecular and cellular biology</subject><subject>MOLECULAR STRUCTURE</subject><subject>NUCLEAR MAGNETIC RESONANCE</subject><subject>NUCLEI</subject><subject>NUCLEONS</subject><subject>ODD-EVEN NUCLEI</subject><subject>ORGANIC COMPOUNDS</subject><subject>Phosphorus</subject><subject>PHOSPHORUS 31</subject><subject>PHOSPHORUS ISOTOPES</subject><subject>POLYSACCHARIDES</subject><subject>Polysaccharides, Bacterial</subject><subject>PROTEINS</subject><subject>PROTONS</subject><subject>RADIOLOGY AND NUCLEAR MEDICINE</subject><subject>RECEPTORS</subject><subject>RESONANCE</subject><subject>SACCHARIDES</subject><subject>STABLE ISOTOPES</subject><subject>STEREOCHEMISTRY</subject><subject>STREPTOCOCCUS</subject><subject>Streptococcus sanguis</subject><issn>0006-2960</issn><issn>1520-4995</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1990</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0N9r1TAUB_AgyrybPvksFBF9GNWTNGmaR3eZm2Pgj03ZW0jPTb2dbVNzUnD__Tp6ufiwp3D4fvgSvoy94vCBg-Af6xZAqsJBIZ6wFVcCcmmMespWAFDmwpTwnB0S3c6nBC0P2IHgSkttVuxsHfqx88lnlOKEaYo-C02Wtj4bQ3dHDnHrYrvxWRNDn12l6McUMCBOlJEbfk8tZRdCvGDPGteRf7l7j9jPz6fX6_P88uvZl_Wny9xJDilXsnFKeZSFrLFELXDDfQMNV1VpRC14VUlfNLVwAqqS17LidcURVaU3WmNVHLE3S2-g1FrCNnncYhgGj8lqACN0MaN3Cxpj-Dt5SrZvCX3XucGHiaw2GkwBD23HC8QYiKJv7Bjb3sU7y8E-bGv_23bWr3e1U937zd7uxpzzt7vcEbquiW7AlvasLI2cq2aWL6yl5P_tYxf_2FIXWtnrb1f21_mPk5vvN8qezP794h2SvQ1THOaBH_3gPRTwmzs</recordid><startdate>19900109</startdate><enddate>19900109</enddate><creator>Abeygunawardana, Chitrananda</creator><creator>Bush, C. Allen</creator><creator>Cisar, John O</creator><general>American Chemical Society</general><scope>BSCLL</scope><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><scope>OTOTI</scope></search><sort><creationdate>19900109</creationdate><title>Complete structure of the polysaccharide from Streptococcus sanguis J22</title><author>Abeygunawardana, Chitrananda ; Bush, C. Allen ; Cisar, John O</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a410t-54fa55ec434bc6c72cd1ef0f158692b21884e3fb2a20861b481b81cc587d77c83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1990</creationdate><topic>550601 - Medicine- Unsealed Radionuclides in Diagnostics</topic><topic>BACTERIA</topic><topic>BARYONS</topic><topic>Biological and medical sciences</topic><topic>Carbohydrate Conformation</topic><topic>CARBOHYDRATES</topic><topic>CARBON 13</topic><topic>CARBON ISOTOPES</topic><topic>CELL CONSTITUENTS</topic><topic>Cell receptors</topic><topic>Cell structures and functions</topic><topic>CELL WALL</topic><topic>Cell Wall - ultrastructure</topic><topic>CHEMICAL BONDS</topic><topic>ELEMENTARY PARTICLES</topic><topic>EVEN-ODD NUCLEI</topic><topic>FERMIONS</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>HADRONS</topic><topic>ISOTOPES</topic><topic>LIGHT NUCLEI</topic><topic>MAGNETIC RESONANCE</topic><topic>Magnetic Resonance Spectroscopy - methods</topic><topic>MEMBRANE PROTEINS</topic><topic>MICROORGANISMS</topic><topic>Molecular and cellular biology</topic><topic>MOLECULAR STRUCTURE</topic><topic>NUCLEAR MAGNETIC RESONANCE</topic><topic>NUCLEI</topic><topic>NUCLEONS</topic><topic>ODD-EVEN NUCLEI</topic><topic>ORGANIC COMPOUNDS</topic><topic>Phosphorus</topic><topic>PHOSPHORUS 31</topic><topic>PHOSPHORUS ISOTOPES</topic><topic>POLYSACCHARIDES</topic><topic>Polysaccharides, Bacterial</topic><topic>PROTEINS</topic><topic>PROTONS</topic><topic>RADIOLOGY AND NUCLEAR MEDICINE</topic><topic>RECEPTORS</topic><topic>RESONANCE</topic><topic>SACCHARIDES</topic><topic>STABLE ISOTOPES</topic><topic>STEREOCHEMISTRY</topic><topic>STREPTOCOCCUS</topic><topic>Streptococcus sanguis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Abeygunawardana, Chitrananda</creatorcontrib><creatorcontrib>Bush, C. Allen</creatorcontrib><creatorcontrib>Cisar, John O</creatorcontrib><collection>Istex</collection><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><collection>OSTI.GOV</collection><jtitle>Biochemistry (Easton)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Abeygunawardana, Chitrananda</au><au>Bush, C. Allen</au><au>Cisar, John O</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Complete structure of the polysaccharide from Streptococcus sanguis J22</atitle><jtitle>Biochemistry (Easton)</jtitle><addtitle>Biochemistry</addtitle><date>1990-01-09</date><risdate>1990</risdate><volume>29</volume><issue>1</issue><spage>234</spage><epage>248</epage><pages>234-248</pages><issn>0006-2960</issn><eissn>1520-4995</eissn><abstract>The cell wall polysaccharides of certain oral streptococci such as Streptococcus sanguis strains 34 and J22, although immunologically distinct, act as receptors for the fimbrial lectins of Actinomyces viscosus T14V. We report the complete covalent structure of the polysaccharide from S. sanguis J22 which is composed of a heptasaccharide subunit linked by phosphodiester bonds. The repeating subunit, which contains alpha-GalNAc, alpha-rhamnose, beta-rhamnose, beta-glucose, and beta-galactose all in the pyranoside form and beta-galactofuranose, is compared with the previously published structure of the polysaccharide from strain 34. The structure has been determined almost exclusively by high-resolution nuclear magnetic resonance methods. The 1H and 13C NMR spectra of the polysaccharides from both strains 34 and J22 have been completely assigned. The stereochemistry of pyranosides was assigned from JH-H values determined from phase-sensitive COSY spectra, and acetamido sugars were assigned by correlation of the resonances of the amide 1H with the sugar ring protons. The 13C spectra were assigned by 1H-detected multiple-quantum correlation (HMQC) spectra, and the assignments were confirmed by 1H-detected multiple-bond correlation (HMBC) spectra. The positions of the glycosidic linkages were assigned by detection of three-bond 1H-13C correlation across the glycosidic linkage in the HMBC spectra. The positions of the phosphodiester linkages were determined by splittings observed in the 13C resonances due to 31P coupling and also by 1H-detected 31P correlation spectroscopy.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>2157479</pmid><doi>10.1021/bi00453a032</doi><tpages>15</tpages></addata></record> |
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| ispartof | Biochemistry (Easton), 1990-01, Vol.29 (1), p.234-248 |
| issn | 0006-2960 1520-4995 |
| language | eng |
| recordid | cdi_osti_scitechconnect_7009273 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | 550601 - Medicine- Unsealed Radionuclides in Diagnostics BACTERIA BARYONS Biological and medical sciences Carbohydrate Conformation CARBOHYDRATES CARBON 13 CARBON ISOTOPES CELL CONSTITUENTS Cell receptors Cell structures and functions CELL WALL Cell Wall - ultrastructure CHEMICAL BONDS ELEMENTARY PARTICLES EVEN-ODD NUCLEI FERMIONS Fundamental and applied biological sciences. Psychology HADRONS ISOTOPES LIGHT NUCLEI MAGNETIC RESONANCE Magnetic Resonance Spectroscopy - methods MEMBRANE PROTEINS MICROORGANISMS Molecular and cellular biology MOLECULAR STRUCTURE NUCLEAR MAGNETIC RESONANCE NUCLEI NUCLEONS ODD-EVEN NUCLEI ORGANIC COMPOUNDS Phosphorus PHOSPHORUS 31 PHOSPHORUS ISOTOPES POLYSACCHARIDES Polysaccharides, Bacterial PROTEINS PROTONS RADIOLOGY AND NUCLEAR MEDICINE RECEPTORS RESONANCE SACCHARIDES STABLE ISOTOPES STEREOCHEMISTRY STREPTOCOCCUS Streptococcus sanguis |
| title | Complete structure of the polysaccharide from Streptococcus sanguis J22 |
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