Synthesis and X-ray crystal and solution structures of 2,5-anhydro-3,4- O-(1,2-ethanediyl)- d-mannitol: a locked 4T3 furanose conformer
2,5-Anhydro-3,4- O-(1,2-ethanedyl)- d-mannitol ( 1) was prepared from 2,5-anhydro- d-mannitol ( 2) in three steps. The fused ring system was introduced by a phase-transfer alkylation using 1,2-dibromoethane. Its conformation in solution was determined by NMR studies at 500 MHz. Variable-temperature...
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| Veröffentlicht in: | Carbohydrate research 1992-06, Vol.230 (2), p.213-222 |
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| creator | Voll, Ronald J. Fronczek, Frank R. Vargas, David Younathan, Ezzat S. |
| description | 2,5-Anhydro-3,4-
O-(1,2-ethanedyl)-
d-mannitol (
1) was prepared from 2,5-anhydro-
d-mannitol (
2) in three steps. The fused ring system was introduced by a phase-transfer alkylation using 1,2-dibromoethane. Its conformation in solution was determined by NMR studies at 500 MHz. Variable-temperature studies showed no lineshape change from 25 to 80° in D
2O. The data indicate that the five-membered ring is locked by the
trans-fused six-membered 1,4-dioxane ring into a twist
4
T
3 conformation. A single-crystal X-ray study was carried out. The crystals are orthorhombic,
C222
1,
a= 4.7252 (6),
b = 14.0364 (12),
c = 13.268 (2) Å,
Z = 4, with
R = 0.032 for 894 observations. The molecule lies upon a crystallographic two-fold axis, and thus five-membered ring exists in a perfect
4
T
3 conformation with a pseudorotation angle of 0° and amplitude of 47.2°, in agreement with the NMR results. We have shown earlier that, among twenty possible conformers, phosphofructokinase acts specifically on the
4
T
3 conformer of the β anomer of
dfructose 6-phosphate. |
| doi_str_mv | 10.1016/0008-6215(92)84034-P |
| format | Article |
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O-(1,2-ethanedyl)-
d-mannitol (
1) was prepared from 2,5-anhydro-
d-mannitol (
2) in three steps. The fused ring system was introduced by a phase-transfer alkylation using 1,2-dibromoethane. Its conformation in solution was determined by NMR studies at 500 MHz. Variable-temperature studies showed no lineshape change from 25 to 80° in D
2O. The data indicate that the five-membered ring is locked by the
trans-fused six-membered 1,4-dioxane ring into a twist
4
T
3 conformation. A single-crystal X-ray study was carried out. The crystals are orthorhombic,
C222
1,
a= 4.7252 (6),
b = 14.0364 (12),
c = 13.268 (2) Å,
Z = 4, with
R = 0.032 for 894 observations. The molecule lies upon a crystallographic two-fold axis, and thus five-membered ring exists in a perfect
4
T
3 conformation with a pseudorotation angle of 0° and amplitude of 47.2°, in agreement with the NMR results. We have shown earlier that, among twenty possible conformers, phosphofructokinase acts specifically on the
4
T
3 conformer of the β anomer of
dfructose 6-phosphate.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/0008-6215(92)84034-P</identifier><identifier>PMID: 1394297</identifier><identifier>CODEN: CRBRAT</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Carbohydrate Conformation ; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides ; Carbohydrates. Nucleosides and nucleotides ; Chemistry ; Condensed matter: structure, mechanical and thermal properties ; Exact sciences and technology ; Heterocyclic compounds ; Indicators and Reagents ; Magnetic Resonance Spectroscopy ; Mannitol - analogs & derivatives ; Mannitol - chemical synthesis ; Mannitol - chemistry ; Models, Molecular ; Molecular Structure ; Organic chemistry ; Organic compounds ; Physics ; Preparations and properties ; Solutions ; Structure of solids and liquids; crystallography ; Structure of specific crystalline solids ; X-Ray Diffraction</subject><ispartof>Carbohydrate research, 1992-06, Vol.230 (2), p.213-222</ispartof><rights>1992</rights><rights>1992 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c267t-69646a47a61be1e1cc54818af2c7aead1cff4e64706763fd7b5342ba59f5362a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/0008-6215(92)84034-P$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=5361512$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/1394297$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Voll, Ronald J.</creatorcontrib><creatorcontrib>Fronczek, Frank R.</creatorcontrib><creatorcontrib>Vargas, David</creatorcontrib><creatorcontrib>Younathan, Ezzat S.</creatorcontrib><title>Synthesis and X-ray crystal and solution structures of 2,5-anhydro-3,4- O-(1,2-ethanediyl)- d-mannitol: a locked 4T3 furanose conformer</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>2,5-Anhydro-3,4-
O-(1,2-ethanedyl)-
d-mannitol (
1) was prepared from 2,5-anhydro-
d-mannitol (
2) in three steps. The fused ring system was introduced by a phase-transfer alkylation using 1,2-dibromoethane. Its conformation in solution was determined by NMR studies at 500 MHz. Variable-temperature studies showed no lineshape change from 25 to 80° in D
2O. The data indicate that the five-membered ring is locked by the
trans-fused six-membered 1,4-dioxane ring into a twist
4
T
3 conformation. A single-crystal X-ray study was carried out. The crystals are orthorhombic,
C222
1,
a= 4.7252 (6),
b = 14.0364 (12),
c = 13.268 (2) Å,
Z = 4, with
R = 0.032 for 894 observations. The molecule lies upon a crystallographic two-fold axis, and thus five-membered ring exists in a perfect
4
T
3 conformation with a pseudorotation angle of 0° and amplitude of 47.2°, in agreement with the NMR results. We have shown earlier that, among twenty possible conformers, phosphofructokinase acts specifically on the
4
T
3 conformer of the β anomer of
dfructose 6-phosphate.</description><subject>Carbohydrate Conformation</subject><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Condensed matter: structure, mechanical and thermal properties</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Indicators and Reagents</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mannitol - analogs & derivatives</subject><subject>Mannitol - chemical synthesis</subject><subject>Mannitol - chemistry</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Organic compounds</subject><subject>Physics</subject><subject>Preparations and properties</subject><subject>Solutions</subject><subject>Structure of solids and liquids; crystallography</subject><subject>Structure of specific crystalline solids</subject><subject>X-Ray Diffraction</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1992</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kF1rFDEUhoModVv9Bwq5EGlho5OPSWa8EErxCwotWKF3IZs5YaMzSZtkhPkF_m2z3aXeeXXIOc85vHkQekWbd7Sh8n3TNB2RjLanPTvrRMMFuX6CVrRTnAgmb5-i1SPyHB3n_LM-G6nkETqivBesVyv05_sSyhayz9iEAd-SZBZs05KLGR86OY5z8THgXNJsy5wg4-gwW7fEhO0ypEj4WhB8RU7pmhEoWxNg8Mt4RvBAJhOCL3H8gA0eo_0FAxY3HLs5mRAzYBuDi2mC9AI9c2bM8PJQT9CPz59uLr6Sy6sv3y7OL4llUhUieymkEcpIugEK1NpWdLQzjlllwAzUOidACrX7J3eD2rRcsI1pe9dyyQw_QW_3d-9SvJ8hFz35bGEca-o4Z6047RXtRQXFHrQp5pzA6bvkJ5MWTRu98693cvVOru6ZfvCvr-va68P9eTPB8G9pL7zO3xzmJlszuurB-vyI1ZC0paxiH_cYVBe_PSSdrYdgq9kEtugh-v_n-AtoNqBn</recordid><startdate>19920616</startdate><enddate>19920616</enddate><creator>Voll, Ronald J.</creator><creator>Fronczek, Frank R.</creator><creator>Vargas, David</creator><creator>Younathan, Ezzat S.</creator><general>Elsevier Ltd</general><general>Elsevier Science</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>19920616</creationdate><title>Synthesis and X-ray crystal and solution structures of 2,5-anhydro-3,4- O-(1,2-ethanediyl)- d-mannitol: a locked 4T3 furanose conformer</title><author>Voll, Ronald J. ; Fronczek, Frank R. ; Vargas, David ; Younathan, Ezzat S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c267t-69646a47a61be1e1cc54818af2c7aead1cff4e64706763fd7b5342ba59f5362a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1992</creationdate><topic>Carbohydrate Conformation</topic><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Condensed matter: structure, mechanical and thermal properties</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Indicators and Reagents</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mannitol - analogs & derivatives</topic><topic>Mannitol - chemical synthesis</topic><topic>Mannitol - chemistry</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Organic compounds</topic><topic>Physics</topic><topic>Preparations and properties</topic><topic>Solutions</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>Voll, Ronald J.</creatorcontrib><creatorcontrib>Fronczek, Frank R.</creatorcontrib><creatorcontrib>Vargas, David</creatorcontrib><creatorcontrib>Younathan, Ezzat S.</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>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Voll, Ronald J.</au><au>Fronczek, Frank R.</au><au>Vargas, David</au><au>Younathan, Ezzat S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and X-ray crystal and solution structures of 2,5-anhydro-3,4- O-(1,2-ethanediyl)- d-mannitol: a locked 4T3 furanose conformer</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>1992-06-16</date><risdate>1992</risdate><volume>230</volume><issue>2</issue><spage>213</spage><epage>222</epage><pages>213-222</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><coden>CRBRAT</coden><abstract>2,5-Anhydro-3,4-
O-(1,2-ethanedyl)-
d-mannitol (
1) was prepared from 2,5-anhydro-
d-mannitol (
2) in three steps. The fused ring system was introduced by a phase-transfer alkylation using 1,2-dibromoethane. Its conformation in solution was determined by NMR studies at 500 MHz. Variable-temperature studies showed no lineshape change from 25 to 80° in D
2O. The data indicate that the five-membered ring is locked by the
trans-fused six-membered 1,4-dioxane ring into a twist
4
T
3 conformation. A single-crystal X-ray study was carried out. The crystals are orthorhombic,
C222
1,
a= 4.7252 (6),
b = 14.0364 (12),
c = 13.268 (2) Å,
Z = 4, with
R = 0.032 for 894 observations. The molecule lies upon a crystallographic two-fold axis, and thus five-membered ring exists in a perfect
4
T
3 conformation with a pseudorotation angle of 0° and amplitude of 47.2°, in agreement with the NMR results. We have shown earlier that, among twenty possible conformers, phosphofructokinase acts specifically on the
4
T
3 conformer of the β anomer of
dfructose 6-phosphate.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>1394297</pmid><doi>10.1016/0008-6215(92)84034-P</doi><tpages>10</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0008-6215 |
| ispartof | Carbohydrate research, 1992-06, Vol.230 (2), p.213-222 |
| issn | 0008-6215 1873-426X |
| language | eng |
| recordid | cdi_proquest_miscellaneous_73197194 |
| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Carbohydrate Conformation Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Condensed matter: structure, mechanical and thermal properties Exact sciences and technology Heterocyclic compounds Indicators and Reagents Magnetic Resonance Spectroscopy Mannitol - analogs & derivatives Mannitol - chemical synthesis Mannitol - chemistry Models, Molecular Molecular Structure Organic chemistry Organic compounds Physics Preparations and properties Solutions Structure of solids and liquids crystallography Structure of specific crystalline solids X-Ray Diffraction |
| title | Synthesis and X-ray crystal and solution structures of 2,5-anhydro-3,4- O-(1,2-ethanediyl)- d-mannitol: a locked 4T3 furanose conformer |
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