Structure of a novel cofactor containing N-(7-mercaptoheptanoyl)-O-3-phosphothreonine
The cofactor required in the methylcoenzyme M methylreductase reaction was shown to be a large molecule with an Mr of 1149.21 in the free acid form. The cofactor, named MRF for methyl reducing factor, was identified from analyses by fast atom bombardment mass spectrometry and 1H, 13C, and 31P NMR sp...
Gespeichert in:
| Veröffentlicht in: | Biochemistry (Easton) 1990-08, Vol.29 (33), p.7593-7600 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 7600 |
|---|---|
| container_issue | 33 |
| container_start_page | 7593 |
| container_title | Biochemistry (Easton) |
| container_volume | 29 |
| creator | Sauer, Frank D Blackwell, Barbara A Kramer, John K. G Marsden, Brian J |
| description | The cofactor required in the methylcoenzyme M methylreductase reaction was shown to be a large molecule with an Mr of 1149.21 in the free acid form. The cofactor, named MRF for methyl reducing factor, was identified from analyses by fast atom bombardment mass spectrometry and 1H, 13C, and 31P NMR spectroscopy as uridine 5'-[N-(7-mercaptoheptanoyl)-O-3-phosphothreonine-P-yl(2-acetamido- 2-deoxy- beta-mannopyranuronosyl)(acid anhydride)]-(1---4)-O-2-acetamido-2-deoxy- alpha-glucopyranosyl diphosphate. MRF contains N-(7-mercaptoheptanoyl)threonine O-3-phosphate (HS-HTP) [No11, K. M., Rinehart, K. L., Tanner, R. S., & Wolfe, R. S. (1986) Proc. Natl. Acad. Sci. U.S.A. 83, 4238-4242] and is linked to C-6 of 2-acetamido-2-deoxymannopyranuronic acid of the UDP-disaccharide through a carboxylic-phosphoric anhydride linkage. It is postulated that this bond is responsible for the instability of the molecule and its hydrolysis during isolation. Analyses of Eadie and Hofstee plots of the methylcoenzyme M methylreductase reaction indicate that MRF has a 6-fold lower Km(app) than HS-HTP and a 50% greater Vmax. This suggests that the UDP-disaccharide moiety may be of importance in the binding of MRF to the enzyme active site. |
| doi_str_mv | 10.1021/bi00485a008 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_osti_</sourceid><recordid>TN_cdi_osti_scitechconnect_5935237</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>80212189</sourcerecordid><originalsourceid>FETCH-LOGICAL-a411t-352298ab0ef9daff65729e5f0108b1dd7e99405a0169ff787220625c787516383</originalsourceid><addsrcrecordid>eNptkM2LFDEQxYMo67h68iw0wvqBRCvpTic5yuB-wOIKMyveQiaTOFl7kjZJi_vfm6WH1YOHoqp4Px5VD6HnBN4ToOTDxgN0gmkA8QAtCKOAOynZQ7QAgB5T2cNj9CTnm7p2wLsjdEQpJ4zIBbpelTSZMiXbRNfoJsRfdmhMdNqUmOoQivbBh-_NZ_yG471NRo8l7uxYdIi3w1t8hVs87mKuVXbJxgrbp-iR00O2zw79GF2fflovz_Hl1dnF8uMl1h0hBbeMUin0BqyTW-1czziVljkgIDZku-VWyg7qY6SXznHBKYWeMlMnRvpWtMfo5ewbc_EqG1-s2dWbgzVFMVn9W16hVzM0pvhzsrmovc_GDoMONk5ZiZohJUJW8N0MmhRzTtapMfm9TreKgLpLWv2TdKVfHGynzd5u79lDtFU_Oeg6Gz24pIPx-a-lZJ2oH1UOz5zPxf6-13X6oXrecqbWX1bq23K94vCVqNPKv555bbK6iVMKNeH_XvgHFlKfOg</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>80212189</pqid></control><display><type>article</type><title>Structure of a novel cofactor containing N-(7-mercaptoheptanoyl)-O-3-phosphothreonine</title><source>MEDLINE</source><source>ACS Publications</source><creator>Sauer, Frank D ; Blackwell, Barbara A ; Kramer, John K. G ; Marsden, Brian J</creator><creatorcontrib>Sauer, Frank D ; Blackwell, Barbara A ; Kramer, John K. G ; Marsden, Brian J</creatorcontrib><description>The cofactor required in the methylcoenzyme M methylreductase reaction was shown to be a large molecule with an Mr of 1149.21 in the free acid form. The cofactor, named MRF for methyl reducing factor, was identified from analyses by fast atom bombardment mass spectrometry and 1H, 13C, and 31P NMR spectroscopy as uridine 5'-[N-(7-mercaptoheptanoyl)-O-3-phosphothreonine-P-yl(2-acetamido- 2-deoxy- beta-mannopyranuronosyl)(acid anhydride)]-(1---4)-O-2-acetamido-2-deoxy- alpha-glucopyranosyl diphosphate. MRF contains N-(7-mercaptoheptanoyl)threonine O-3-phosphate (HS-HTP) [No11, K. M., Rinehart, K. L., Tanner, R. S., & Wolfe, R. S. (1986) Proc. Natl. Acad. Sci. U.S.A. 83, 4238-4242] and is linked to C-6 of 2-acetamido-2-deoxymannopyranuronic acid of the UDP-disaccharide through a carboxylic-phosphoric anhydride linkage. It is postulated that this bond is responsible for the instability of the molecule and its hydrolysis during isolation. Analyses of Eadie and Hofstee plots of the methylcoenzyme M methylreductase reaction indicate that MRF has a 6-fold lower Km(app) than HS-HTP and a 50% greater Vmax. This suggests that the UDP-disaccharide moiety may be of importance in the binding of MRF to the enzyme active site.</description><identifier>ISSN: 0006-2960</identifier><identifier>EISSN: 1520-4995</identifier><identifier>DOI: 10.1021/bi00485a008</identifier><identifier>PMID: 2271519</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>550601 - Medicine- Unsealed Radionuclides in Diagnostics ; AMINO ACIDS ; Analytical, structural and metabolic biochemistry ; BACTERIA ; BARYONS ; Binding Sites ; BIOCHEMICAL REACTION KINETICS ; Biological and medical sciences ; Carbohydrate Sequence ; CARBOHYDRATES ; CARBOXYLIC ACIDS ; CHEMICAL SHIFT ; COENZYMES ; DISACCHARIDES ; ELEMENTARY PARTICLES ; ENZYMES ; Enzymes and enzyme inhibitors ; FERMIONS ; Fundamental and applied biological sciences. Psychology ; HADRONS ; HYDROXY ACIDS ; KINETICS ; MAGNETIC RESONANCE ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; MASS SPECTROSCOPY ; METHANOGENIC BACTERIA ; Methylation ; MICROORGANISMS ; Molecular Sequence Data ; MOLECULAR WEIGHT ; NUCLEAR MAGNETIC RESONANCE ; NUCLEONS ; OLIGOSACCHARIDES ; ORGANIC ACIDS ; ORGANIC COMPOUNDS ; OXIDOREDUCTASES ; Oxidoreductases - chemistry ; Phosphothreonine - analogs & derivatives ; Phosphothreonine - chemistry ; PROTONS ; RADIOLOGY AND NUCLEAR MEDICINE ; REACTION KINETICS ; RESONANCE ; SACCHARIDES ; SPECTROSCOPY ; THREONINE ; Uridine Diphosphate - analogs & derivatives ; Uridine Diphosphate - chemistry</subject><ispartof>Biochemistry (Easton), 1990-08, Vol.29 (33), p.7593-7600</ispartof><rights>1991 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a411t-352298ab0ef9daff65729e5f0108b1dd7e99405a0169ff787220625c787516383</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/bi00485a008$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/bi00485a008$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,777,781,882,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=19548872$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/2271519$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/5935237$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Sauer, Frank D</creatorcontrib><creatorcontrib>Blackwell, Barbara A</creatorcontrib><creatorcontrib>Kramer, John K. G</creatorcontrib><creatorcontrib>Marsden, Brian J</creatorcontrib><title>Structure of a novel cofactor containing N-(7-mercaptoheptanoyl)-O-3-phosphothreonine</title><title>Biochemistry (Easton)</title><addtitle>Biochemistry</addtitle><description>The cofactor required in the methylcoenzyme M methylreductase reaction was shown to be a large molecule with an Mr of 1149.21 in the free acid form. The cofactor, named MRF for methyl reducing factor, was identified from analyses by fast atom bombardment mass spectrometry and 1H, 13C, and 31P NMR spectroscopy as uridine 5'-[N-(7-mercaptoheptanoyl)-O-3-phosphothreonine-P-yl(2-acetamido- 2-deoxy- beta-mannopyranuronosyl)(acid anhydride)]-(1---4)-O-2-acetamido-2-deoxy- alpha-glucopyranosyl diphosphate. MRF contains N-(7-mercaptoheptanoyl)threonine O-3-phosphate (HS-HTP) [No11, K. M., Rinehart, K. L., Tanner, R. S., & Wolfe, R. S. (1986) Proc. Natl. Acad. Sci. U.S.A. 83, 4238-4242] and is linked to C-6 of 2-acetamido-2-deoxymannopyranuronic acid of the UDP-disaccharide through a carboxylic-phosphoric anhydride linkage. It is postulated that this bond is responsible for the instability of the molecule and its hydrolysis during isolation. Analyses of Eadie and Hofstee plots of the methylcoenzyme M methylreductase reaction indicate that MRF has a 6-fold lower Km(app) than HS-HTP and a 50% greater Vmax. This suggests that the UDP-disaccharide moiety may be of importance in the binding of MRF to the enzyme active site.</description><subject>550601 - Medicine- Unsealed Radionuclides in Diagnostics</subject><subject>AMINO ACIDS</subject><subject>Analytical, structural and metabolic biochemistry</subject><subject>BACTERIA</subject><subject>BARYONS</subject><subject>Binding Sites</subject><subject>BIOCHEMICAL REACTION KINETICS</subject><subject>Biological and medical sciences</subject><subject>Carbohydrate Sequence</subject><subject>CARBOHYDRATES</subject><subject>CARBOXYLIC ACIDS</subject><subject>CHEMICAL SHIFT</subject><subject>COENZYMES</subject><subject>DISACCHARIDES</subject><subject>ELEMENTARY PARTICLES</subject><subject>ENZYMES</subject><subject>Enzymes and enzyme inhibitors</subject><subject>FERMIONS</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>HADRONS</subject><subject>HYDROXY ACIDS</subject><subject>KINETICS</subject><subject>MAGNETIC RESONANCE</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>MASS SPECTROSCOPY</subject><subject>METHANOGENIC BACTERIA</subject><subject>Methylation</subject><subject>MICROORGANISMS</subject><subject>Molecular Sequence Data</subject><subject>MOLECULAR WEIGHT</subject><subject>NUCLEAR MAGNETIC RESONANCE</subject><subject>NUCLEONS</subject><subject>OLIGOSACCHARIDES</subject><subject>ORGANIC ACIDS</subject><subject>ORGANIC COMPOUNDS</subject><subject>OXIDOREDUCTASES</subject><subject>Oxidoreductases - chemistry</subject><subject>Phosphothreonine - analogs & derivatives</subject><subject>Phosphothreonine - chemistry</subject><subject>PROTONS</subject><subject>RADIOLOGY AND NUCLEAR MEDICINE</subject><subject>REACTION KINETICS</subject><subject>RESONANCE</subject><subject>SACCHARIDES</subject><subject>SPECTROSCOPY</subject><subject>THREONINE</subject><subject>Uridine Diphosphate - analogs & derivatives</subject><subject>Uridine Diphosphate - chemistry</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>eNptkM2LFDEQxYMo67h68iw0wvqBRCvpTic5yuB-wOIKMyveQiaTOFl7kjZJi_vfm6WH1YOHoqp4Px5VD6HnBN4ToOTDxgN0gmkA8QAtCKOAOynZQ7QAgB5T2cNj9CTnm7p2wLsjdEQpJ4zIBbpelTSZMiXbRNfoJsRfdmhMdNqUmOoQivbBh-_NZ_yG471NRo8l7uxYdIi3w1t8hVs87mKuVXbJxgrbp-iR00O2zw79GF2fflovz_Hl1dnF8uMl1h0hBbeMUin0BqyTW-1czziVljkgIDZku-VWyg7qY6SXznHBKYWeMlMnRvpWtMfo5ewbc_EqG1-s2dWbgzVFMVn9W16hVzM0pvhzsrmovc_GDoMONk5ZiZohJUJW8N0MmhRzTtapMfm9TreKgLpLWv2TdKVfHGynzd5u79lDtFU_Oeg6Gz24pIPx-a-lZJ2oH1UOz5zPxf6-13X6oXrecqbWX1bq23K94vCVqNPKv555bbK6iVMKNeH_XvgHFlKfOg</recordid><startdate>19900821</startdate><enddate>19900821</enddate><creator>Sauer, Frank D</creator><creator>Blackwell, Barbara A</creator><creator>Kramer, John K. G</creator><creator>Marsden, Brian J</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>19900821</creationdate><title>Structure of a novel cofactor containing N-(7-mercaptoheptanoyl)-O-3-phosphothreonine</title><author>Sauer, Frank D ; Blackwell, Barbara A ; Kramer, John K. G ; Marsden, Brian J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a411t-352298ab0ef9daff65729e5f0108b1dd7e99405a0169ff787220625c787516383</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1990</creationdate><topic>550601 - Medicine- Unsealed Radionuclides in Diagnostics</topic><topic>AMINO ACIDS</topic><topic>Analytical, structural and metabolic biochemistry</topic><topic>BACTERIA</topic><topic>BARYONS</topic><topic>Binding Sites</topic><topic>BIOCHEMICAL REACTION KINETICS</topic><topic>Biological and medical sciences</topic><topic>Carbohydrate Sequence</topic><topic>CARBOHYDRATES</topic><topic>CARBOXYLIC ACIDS</topic><topic>CHEMICAL SHIFT</topic><topic>COENZYMES</topic><topic>DISACCHARIDES</topic><topic>ELEMENTARY PARTICLES</topic><topic>ENZYMES</topic><topic>Enzymes and enzyme inhibitors</topic><topic>FERMIONS</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>HADRONS</topic><topic>HYDROXY ACIDS</topic><topic>KINETICS</topic><topic>MAGNETIC RESONANCE</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>MASS SPECTROSCOPY</topic><topic>METHANOGENIC BACTERIA</topic><topic>Methylation</topic><topic>MICROORGANISMS</topic><topic>Molecular Sequence Data</topic><topic>MOLECULAR WEIGHT</topic><topic>NUCLEAR MAGNETIC RESONANCE</topic><topic>NUCLEONS</topic><topic>OLIGOSACCHARIDES</topic><topic>ORGANIC ACIDS</topic><topic>ORGANIC COMPOUNDS</topic><topic>OXIDOREDUCTASES</topic><topic>Oxidoreductases - chemistry</topic><topic>Phosphothreonine - analogs & derivatives</topic><topic>Phosphothreonine - chemistry</topic><topic>PROTONS</topic><topic>RADIOLOGY AND NUCLEAR MEDICINE</topic><topic>REACTION KINETICS</topic><topic>RESONANCE</topic><topic>SACCHARIDES</topic><topic>SPECTROSCOPY</topic><topic>THREONINE</topic><topic>Uridine Diphosphate - analogs & derivatives</topic><topic>Uridine Diphosphate - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sauer, Frank D</creatorcontrib><creatorcontrib>Blackwell, Barbara A</creatorcontrib><creatorcontrib>Kramer, John K. G</creatorcontrib><creatorcontrib>Marsden, Brian J</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>Sauer, Frank D</au><au>Blackwell, Barbara A</au><au>Kramer, John K. G</au><au>Marsden, Brian J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structure of a novel cofactor containing N-(7-mercaptoheptanoyl)-O-3-phosphothreonine</atitle><jtitle>Biochemistry (Easton)</jtitle><addtitle>Biochemistry</addtitle><date>1990-08-21</date><risdate>1990</risdate><volume>29</volume><issue>33</issue><spage>7593</spage><epage>7600</epage><pages>7593-7600</pages><issn>0006-2960</issn><eissn>1520-4995</eissn><abstract>The cofactor required in the methylcoenzyme M methylreductase reaction was shown to be a large molecule with an Mr of 1149.21 in the free acid form. The cofactor, named MRF for methyl reducing factor, was identified from analyses by fast atom bombardment mass spectrometry and 1H, 13C, and 31P NMR spectroscopy as uridine 5'-[N-(7-mercaptoheptanoyl)-O-3-phosphothreonine-P-yl(2-acetamido- 2-deoxy- beta-mannopyranuronosyl)(acid anhydride)]-(1---4)-O-2-acetamido-2-deoxy- alpha-glucopyranosyl diphosphate. MRF contains N-(7-mercaptoheptanoyl)threonine O-3-phosphate (HS-HTP) [No11, K. M., Rinehart, K. L., Tanner, R. S., & Wolfe, R. S. (1986) Proc. Natl. Acad. Sci. U.S.A. 83, 4238-4242] and is linked to C-6 of 2-acetamido-2-deoxymannopyranuronic acid of the UDP-disaccharide through a carboxylic-phosphoric anhydride linkage. It is postulated that this bond is responsible for the instability of the molecule and its hydrolysis during isolation. Analyses of Eadie and Hofstee plots of the methylcoenzyme M methylreductase reaction indicate that MRF has a 6-fold lower Km(app) than HS-HTP and a 50% greater Vmax. This suggests that the UDP-disaccharide moiety may be of importance in the binding of MRF to the enzyme active site.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>2271519</pmid><doi>10.1021/bi00485a008</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0006-2960 |
| ispartof | Biochemistry (Easton), 1990-08, Vol.29 (33), p.7593-7600 |
| issn | 0006-2960 1520-4995 |
| language | eng |
| recordid | cdi_osti_scitechconnect_5935237 |
| source | MEDLINE; ACS Publications |
| subjects | 550601 - Medicine- Unsealed Radionuclides in Diagnostics AMINO ACIDS Analytical, structural and metabolic biochemistry BACTERIA BARYONS Binding Sites BIOCHEMICAL REACTION KINETICS Biological and medical sciences Carbohydrate Sequence CARBOHYDRATES CARBOXYLIC ACIDS CHEMICAL SHIFT COENZYMES DISACCHARIDES ELEMENTARY PARTICLES ENZYMES Enzymes and enzyme inhibitors FERMIONS Fundamental and applied biological sciences. Psychology HADRONS HYDROXY ACIDS KINETICS MAGNETIC RESONANCE Magnetic Resonance Spectroscopy Mass Spectrometry MASS SPECTROSCOPY METHANOGENIC BACTERIA Methylation MICROORGANISMS Molecular Sequence Data MOLECULAR WEIGHT NUCLEAR MAGNETIC RESONANCE NUCLEONS OLIGOSACCHARIDES ORGANIC ACIDS ORGANIC COMPOUNDS OXIDOREDUCTASES Oxidoreductases - chemistry Phosphothreonine - analogs & derivatives Phosphothreonine - chemistry PROTONS RADIOLOGY AND NUCLEAR MEDICINE REACTION KINETICS RESONANCE SACCHARIDES SPECTROSCOPY THREONINE Uridine Diphosphate - analogs & derivatives Uridine Diphosphate - chemistry |
| title | Structure of a novel cofactor containing N-(7-mercaptoheptanoyl)-O-3-phosphothreonine |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-20T01%3A56%3A31IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_osti_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Structure%20of%20a%20novel%20cofactor%20containing%20N-(7-mercaptoheptanoyl)-O-3-phosphothreonine&rft.jtitle=Biochemistry%20(Easton)&rft.au=Sauer,%20Frank%20D&rft.date=1990-08-21&rft.volume=29&rft.issue=33&rft.spage=7593&rft.epage=7600&rft.pages=7593-7600&rft.issn=0006-2960&rft.eissn=1520-4995&rft_id=info:doi/10.1021/bi00485a008&rft_dat=%3Cproquest_osti_%3E80212189%3C/proquest_osti_%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=80212189&rft_id=info:pmid/2271519&rfr_iscdi=true |