Structure and conformation of 3'-O-acetyl-2'-deoxy-5-methoxymethyluridine
C13H18N2O7, Mr = 314.297, triclinic, P1, a = 6.0321 (4), b = 6.775 (5), c = 9.6699 (7) A, alpha = 76.917 (6), beta = 78.871 (6), gamma = 75.344 (6) degrees, V = 368.54 A3, Z = 1, Dm = 1.43, Dx = 1.416 g cm-3, Cu K alpha radiation (Ni filtered), lambda = 1.5418 A, F(000) = 166, T = 287 K, final conve...
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| Veröffentlicht in: | Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 1988-01, Vol.44 (1), p.150-154 |
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| container_title | Acta crystallographica. Section C, Crystal structure communications |
| container_volume | 44 |
| creator | Quail, J. W. Tourigny, G. Delbaere, L. T. J. El-Kabbani, O. A. L. Stuart, A. L. Gupta, S. V. |
| description | C13H18N2O7, Mr = 314.297, triclinic, P1, a = 6.0321 (4), b = 6.775 (5), c = 9.6699 (7) A, alpha = 76.917 (6), beta = 78.871 (6), gamma = 75.344 (6) degrees, V = 368.54 A3, Z = 1, Dm = 1.43, Dx = 1.416 g cm-3, Cu K alpha radiation (Ni filtered), lambda = 1.5418 A, F(000) = 166, T = 287 K, final conventional R factor = 0.034, wR = 0.044 for 1359 reflections and 268 variables. The structure was solved using the XTAL system. The conformation of the furanose ring is best described as intermediate between 2E and 2(1)T: the pseudorotational parameters are P = 148.9 degrees and tau m = 33.4 degrees. The CH2OH, C(5'), side chain has the g+ conformation, the carbonyl bond of the 3'-acetoxy group is syn to the C(3')-O(3',1) bond on the sugar ring and the glycosidic bond conformation is anti [chi = -137.6 (3) degrees]. The methoxy group of the 5-methoxymethyl substituent is on the same side of the pyrimidine plane as O(4') of the furanose ring. Comparison with 2'-deoxy-5-methoxymethyluridine shows that intermolecular attraction have little effect on the internal conformations of the molecule in the solid state. |
| doi_str_mv | 10.1107/S0108270187008850 |
| format | Article |
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W. ; Tourigny, G. ; Delbaere, L. T. J. ; El-Kabbani, O. A. L. ; Stuart, A. L. ; Gupta, S. V.</creator><creatorcontrib>Quail, J. W. ; Tourigny, G. ; Delbaere, L. T. J. ; El-Kabbani, O. A. L. ; Stuart, A. L. ; Gupta, S. V.</creatorcontrib><description>C13H18N2O7, Mr = 314.297, triclinic, P1, a = 6.0321 (4), b = 6.775 (5), c = 9.6699 (7) A, alpha = 76.917 (6), beta = 78.871 (6), gamma = 75.344 (6) degrees, V = 368.54 A3, Z = 1, Dm = 1.43, Dx = 1.416 g cm-3, Cu K alpha radiation (Ni filtered), lambda = 1.5418 A, F(000) = 166, T = 287 K, final conventional R factor = 0.034, wR = 0.044 for 1359 reflections and 268 variables. The structure was solved using the XTAL system. The conformation of the furanose ring is best described as intermediate between 2E and 2(1)T: the pseudorotational parameters are P = 148.9 degrees and tau m = 33.4 degrees. The CH2OH, C(5'), side chain has the g+ conformation, the carbonyl bond of the 3'-acetoxy group is syn to the C(3')-O(3',1) bond on the sugar ring and the glycosidic bond conformation is anti [chi = -137.6 (3) degrees]. The methoxy group of the 5-methoxymethyl substituent is on the same side of the pyrimidine plane as O(4') of the furanose ring. Comparison with 2'-deoxy-5-methoxymethyluridine shows that intermolecular attraction have little effect on the internal conformations of the molecule in the solid state.</description><identifier>ISSN: 0108-2701</identifier><identifier>EISSN: 1600-5759</identifier><identifier>DOI: 10.1107/S0108270187008850</identifier><identifier>PMID: 2856040</identifier><identifier>CODEN: ACSCEE</identifier><language>eng</language><publisher>5 Abbey Square, Chester, Cheshire CH1 2HU, England: International Union of Crystallography</publisher><subject>Antiviral Agents ; Chemical Phenomena ; Chemistry, Physical ; Condensed matter: structure, mechanical and thermal properties ; Crystallization ; Deoxyuridine - analogs & derivatives ; Deoxyuridine - chemical synthesis ; Exact sciences and technology ; Heterocyclic compounds ; Molecular Conformation ; Molecular Structure ; Organic compounds ; Physics ; Prodrugs ; Simplexvirus ; Structure of solids and liquids; crystallography ; Structure of specific crystalline solids ; X-Ray Diffraction</subject><ispartof>Acta crystallographica. 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V.</creatorcontrib><title>Structure and conformation of 3'-O-acetyl-2'-deoxy-5-methoxymethyluridine</title><title>Acta crystallographica. Section C, Crystal structure communications</title><addtitle>Acta Cryst. C</addtitle><description>C13H18N2O7, Mr = 314.297, triclinic, P1, a = 6.0321 (4), b = 6.775 (5), c = 9.6699 (7) A, alpha = 76.917 (6), beta = 78.871 (6), gamma = 75.344 (6) degrees, V = 368.54 A3, Z = 1, Dm = 1.43, Dx = 1.416 g cm-3, Cu K alpha radiation (Ni filtered), lambda = 1.5418 A, F(000) = 166, T = 287 K, final conventional R factor = 0.034, wR = 0.044 for 1359 reflections and 268 variables. The structure was solved using the XTAL system. The conformation of the furanose ring is best described as intermediate between 2E and 2(1)T: the pseudorotational parameters are P = 148.9 degrees and tau m = 33.4 degrees. The CH2OH, C(5'), side chain has the g+ conformation, the carbonyl bond of the 3'-acetoxy group is syn to the C(3')-O(3',1) bond on the sugar ring and the glycosidic bond conformation is anti [chi = -137.6 (3) degrees]. The methoxy group of the 5-methoxymethyl substituent is on the same side of the pyrimidine plane as O(4') of the furanose ring. Comparison with 2'-deoxy-5-methoxymethyluridine shows that intermolecular attraction have little effect on the internal conformations of the molecule in the solid state.</description><subject>Antiviral Agents</subject><subject>Chemical Phenomena</subject><subject>Chemistry, Physical</subject><subject>Condensed matter: structure, mechanical and thermal properties</subject><subject>Crystallization</subject><subject>Deoxyuridine - analogs & derivatives</subject><subject>Deoxyuridine - chemical synthesis</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>Organic compounds</subject><subject>Physics</subject><subject>Prodrugs</subject><subject>Simplexvirus</subject><subject>Structure of solids and liquids; crystallography</subject><subject>Structure of specific crystalline solids</subject><subject>X-Ray Diffraction</subject><issn>0108-2701</issn><issn>1600-5759</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1988</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMtKw0AUhgdRar08gAuhC7Gr0TOTzCVLqVcQC7YiroZxcoLRXHQmQfP2JrR048LVOfB_3znwE3LE4IwxUOcLYKC5AqYVgNYCtsiYSQAqlEi2yXiI6ZDvkr0Q3gGAcx6NyIhrISGGMblbNL51TetxYqt04uoqq31pm7yuJnU2iaZ0Tq3Dpison9IU65-OClpi89Zvw-iK1udpXuEB2clsEfBwPffJ0_XVcnZL7-c3d7OLe-oiGQsqk1eJAiXjWaIxwSxmkVSJspBKB4rFgFZKnsSMOxthAtKJLGWILmYQSxntk9PV3U9ff7UYGlPmwWFR2ArrNhilNQghBpCtQOfrEDxm5tPnpfWdYWCG-syf-nrneH28fS0x3Rjrvvr8ZJ3b4GyReVu5PGwwpSSLheoxvcK-8wK7__-ai5fZ8hGYEr1KV2oeGvzZqNZ_GKkiJczzw42Rs-RyodXS8OgXQmaUSQ</recordid><startdate>19880115</startdate><enddate>19880115</enddate><creator>Quail, J. W.</creator><creator>Tourigny, G.</creator><creator>Delbaere, L. T. J.</creator><creator>El-Kabbani, O. A. L.</creator><creator>Stuart, A. L.</creator><creator>Gupta, S. V.</creator><general>International Union of Crystallography</general><general>Blackwell</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></search><sort><creationdate>19880115</creationdate><title>Structure and conformation of 3'-O-acetyl-2'-deoxy-5-methoxymethyluridine</title><author>Quail, J. W. ; Tourigny, G. ; Delbaere, L. T. J. ; El-Kabbani, O. A. L. ; Stuart, A. L. ; Gupta, S. V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3645-69b6e5e612f98e9ef4136797a0d6c07140ea6629412ca3e906c5fd1eec4104663</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1988</creationdate><topic>Antiviral Agents</topic><topic>Chemical Phenomena</topic><topic>Chemistry, Physical</topic><topic>Condensed matter: structure, mechanical and thermal properties</topic><topic>Crystallization</topic><topic>Deoxyuridine - analogs & derivatives</topic><topic>Deoxyuridine - chemical synthesis</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>Organic compounds</topic><topic>Physics</topic><topic>Prodrugs</topic><topic>Simplexvirus</topic><topic>Structure of solids and liquids; crystallography</topic><topic>Structure of specific crystalline solids</topic><topic>X-Ray Diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Quail, J. W.</creatorcontrib><creatorcontrib>Tourigny, G.</creatorcontrib><creatorcontrib>Delbaere, L. T. J.</creatorcontrib><creatorcontrib>El-Kabbani, O. A. L.</creatorcontrib><creatorcontrib>Stuart, A. L.</creatorcontrib><creatorcontrib>Gupta, S. V.</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><jtitle>Acta crystallographica. Section C, Crystal structure communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Quail, J. W.</au><au>Tourigny, G.</au><au>Delbaere, L. T. J.</au><au>El-Kabbani, O. A. L.</au><au>Stuart, A. L.</au><au>Gupta, S. V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structure and conformation of 3'-O-acetyl-2'-deoxy-5-methoxymethyluridine</atitle><jtitle>Acta crystallographica. Section C, Crystal structure communications</jtitle><addtitle>Acta Cryst. C</addtitle><date>1988-01-15</date><risdate>1988</risdate><volume>44</volume><issue>1</issue><spage>150</spage><epage>154</epage><pages>150-154</pages><issn>0108-2701</issn><eissn>1600-5759</eissn><coden>ACSCEE</coden><abstract>C13H18N2O7, Mr = 314.297, triclinic, P1, a = 6.0321 (4), b = 6.775 (5), c = 9.6699 (7) A, alpha = 76.917 (6), beta = 78.871 (6), gamma = 75.344 (6) degrees, V = 368.54 A3, Z = 1, Dm = 1.43, Dx = 1.416 g cm-3, Cu K alpha radiation (Ni filtered), lambda = 1.5418 A, F(000) = 166, T = 287 K, final conventional R factor = 0.034, wR = 0.044 for 1359 reflections and 268 variables. The structure was solved using the XTAL system. The conformation of the furanose ring is best described as intermediate between 2E and 2(1)T: the pseudorotational parameters are P = 148.9 degrees and tau m = 33.4 degrees. The CH2OH, C(5'), side chain has the g+ conformation, the carbonyl bond of the 3'-acetoxy group is syn to the C(3')-O(3',1) bond on the sugar ring and the glycosidic bond conformation is anti [chi = -137.6 (3) degrees]. The methoxy group of the 5-methoxymethyl substituent is on the same side of the pyrimidine plane as O(4') of the furanose ring. Comparison with 2'-deoxy-5-methoxymethyluridine shows that intermolecular attraction have little effect on the internal conformations of the molecule in the solid state.</abstract><cop>5 Abbey Square, Chester, Cheshire CH1 2HU, England</cop><pub>International Union of Crystallography</pub><pmid>2856040</pmid><doi>10.1107/S0108270187008850</doi><tpages>5</tpages></addata></record> |
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| ispartof | Acta crystallographica. Section C, Crystal structure communications, 1988-01, Vol.44 (1), p.150-154 |
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| source | MEDLINE; Crystallography Journals Online |
| subjects | Antiviral Agents Chemical Phenomena Chemistry, Physical Condensed matter: structure, mechanical and thermal properties Crystallization Deoxyuridine - analogs & derivatives Deoxyuridine - chemical synthesis Exact sciences and technology Heterocyclic compounds Molecular Conformation Molecular Structure Organic compounds Physics Prodrugs Simplexvirus Structure of solids and liquids crystallography Structure of specific crystalline solids X-Ray Diffraction |
| title | Structure and conformation of 3'-O-acetyl-2'-deoxy-5-methoxymethyluridine |
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