Lactosylceramide: Effect of Acyl Chain Structure on Phase Behavior and Molecular Packing
Lactosylceramide (LacCer) is a pivotal intermediate in the metabolism of higher gangliosides, localizes to sphingolipid-sterol “rafts,” and has been implicated in cellular signaling. To provide a fundamental characterization of LacCer phase behavior and intermolecular packing, LacCer containing diff...
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| Veröffentlicht in: | Biophysical journal 2002-09, Vol.83 (3), p.1535-1546 |
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| creator | Li, Xin-Min Momsen, Maureen M. Brockman, Howard L. Brown, Rhoderick E. |
| description | Lactosylceramide (LacCer) is a pivotal intermediate in the metabolism of higher gangliosides, localizes to sphingolipid-sterol “rafts,” and has been implicated in cellular signaling. To provide a fundamental characterization of LacCer phase behavior and intermolecular packing, LacCer containing different saturated (16:0, 18:0, 24:0) or monounsaturated (18:1
Δ9, 24:1
Δ15) acyl chains were synthesized and studied by differential scanning calorimetry and Langmuir film balance approaches. Compared to related sphingoid- and glycerol-based lipids, LacCers containing saturated acyl chains display relatively high thermotropic and pressure-induced transitions. LacCer monolayer films are less elastic in an in-plane sense than sphingomyelin films, but are somewhat more elastic than galactosylceramide films. Together, these findings indicate that the disaccharide headgroup only marginally disrupts gel phase packing and orients more perpendicular than parallel to the interface. This contrasts the reported behavior of digalactosyldiglycerides with saturated acyl chains. Introducing single
cis double bonds into the LacCer acyl chains dramatically lowers the high thermotropic and pressure-induced transitions. Greater reductions occur when
cis double bonds are located near the middle of the acyl chains. The results are discussed in terms of how an extended disaccharide headgroup can enhance interactions among naturally abundant LacCers with saturated acyl chains. |
| doi_str_mv | 10.1016/S0006-3495(02)73923-4 |
| format | Article |
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Δ9, 24:1
Δ15) acyl chains were synthesized and studied by differential scanning calorimetry and Langmuir film balance approaches. Compared to related sphingoid- and glycerol-based lipids, LacCers containing saturated acyl chains display relatively high thermotropic and pressure-induced transitions. LacCer monolayer films are less elastic in an in-plane sense than sphingomyelin films, but are somewhat more elastic than galactosylceramide films. Together, these findings indicate that the disaccharide headgroup only marginally disrupts gel phase packing and orients more perpendicular than parallel to the interface. This contrasts the reported behavior of digalactosyldiglycerides with saturated acyl chains. Introducing single
cis double bonds into the LacCer acyl chains dramatically lowers the high thermotropic and pressure-induced transitions. Greater reductions occur when
cis double bonds are located near the middle of the acyl chains. The results are discussed in terms of how an extended disaccharide headgroup can enhance interactions among naturally abundant LacCers with saturated acyl chains.</description><identifier>ISSN: 0006-3495</identifier><identifier>EISSN: 1542-0086</identifier><identifier>DOI: 10.1016/S0006-3495(02)73923-4</identifier><identifier>PMID: 12202378</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Antigens, CD - chemistry ; Binding Sites ; Biophysical Phenomena ; Biophysics ; Calorimetry, Differential Scanning ; Carbohydrates - chemistry ; Galactosylceramides - chemistry ; Lactosylceramides - chemistry ; Lipids ; Lipids - chemistry ; Metabolism ; Molecular biology ; Sphingomyelins - chemistry ; Temperature</subject><ispartof>Biophysical journal, 2002-09, Vol.83 (3), p.1535-1546</ispartof><rights>2002 The Biophysical Society</rights><rights>Copyright Biophysical Society Sep 2002</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c556t-666d7700b7fb6c84b2bebf7bf33262b0fffc0e3f16effd8f793a876b5db8c9533</citedby><cites>FETCH-LOGICAL-c556t-666d7700b7fb6c84b2bebf7bf33262b0fffc0e3f16effd8f793a876b5db8c9533</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC1302251/pdf/$$EPDF$$P50$$Gpubmedcentral$$H</linktopdf><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0006-3495(02)73923-4$$EHTML$$P50$$Gelsevier$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,3550,27924,27925,45995,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12202378$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Xin-Min</creatorcontrib><creatorcontrib>Momsen, Maureen M.</creatorcontrib><creatorcontrib>Brockman, Howard L.</creatorcontrib><creatorcontrib>Brown, Rhoderick E.</creatorcontrib><title>Lactosylceramide: Effect of Acyl Chain Structure on Phase Behavior and Molecular Packing</title><title>Biophysical journal</title><addtitle>Biophys J</addtitle><description>Lactosylceramide (LacCer) is a pivotal intermediate in the metabolism of higher gangliosides, localizes to sphingolipid-sterol “rafts,” and has been implicated in cellular signaling. To provide a fundamental characterization of LacCer phase behavior and intermolecular packing, LacCer containing different saturated (16:0, 18:0, 24:0) or monounsaturated (18:1
Δ9, 24:1
Δ15) acyl chains were synthesized and studied by differential scanning calorimetry and Langmuir film balance approaches. Compared to related sphingoid- and glycerol-based lipids, LacCers containing saturated acyl chains display relatively high thermotropic and pressure-induced transitions. LacCer monolayer films are less elastic in an in-plane sense than sphingomyelin films, but are somewhat more elastic than galactosylceramide films. Together, these findings indicate that the disaccharide headgroup only marginally disrupts gel phase packing and orients more perpendicular than parallel to the interface. This contrasts the reported behavior of digalactosyldiglycerides with saturated acyl chains. Introducing single
cis double bonds into the LacCer acyl chains dramatically lowers the high thermotropic and pressure-induced transitions. Greater reductions occur when
cis double bonds are located near the middle of the acyl chains. The results are discussed in terms of how an extended disaccharide headgroup can enhance interactions among naturally abundant LacCers with saturated acyl chains.</description><subject>Antigens, CD - chemistry</subject><subject>Binding Sites</subject><subject>Biophysical Phenomena</subject><subject>Biophysics</subject><subject>Calorimetry, Differential Scanning</subject><subject>Carbohydrates - chemistry</subject><subject>Galactosylceramides - chemistry</subject><subject>Lactosylceramides - chemistry</subject><subject>Lipids</subject><subject>Lipids - chemistry</subject><subject>Metabolism</subject><subject>Molecular biology</subject><subject>Sphingomyelins - chemistry</subject><subject>Temperature</subject><issn>0006-3495</issn><issn>1542-0086</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>8G5</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><sourceid>GUQSH</sourceid><sourceid>M2O</sourceid><recordid>eNqFkU1v1DAQhi0EokvhJ4AsDggOgbEd21kOoLIqH9IiKhUkbpbtjLsu2bjYyUr778l-qHxcOPkwz7zjmYeQxwxeMmDq1SUAqErUc_kc-Ast5lxU9R0yY7LmFUCj7pLZLXJCHpRyDcC4BHafnDDOgQvdzMj3pfVDKtvOY7br2OJreh4C-oGmQM_8tqOLlY09vRzy6IcxI009vVjZgvQdruwmpkxt39LPqUM_djbTC-t_xP7qIbkXbFfw0fE9Jd_en39dfKyWXz58WpwtKy-lGiqlVKs1gNPBKd_Ujjt0QbsgBFfcQQjBA4rAFIbQNkHPhW20crJ1jZ9LIU7Jm0PuzejW2Hrsh2w7c5Pj2uatSTaavyt9XJmrtDFMAOeSTQHPjgE5_RyxDGYdi8eusz2msRjNYXdcOYFP_wGv05j7aTnDmdQg632aPEA-p1IyhtufMDA7cWYvzuysGOBmL87UU9-TP9f43XU0NQFvDwBOx9xEzKb4iL3HNuZJl2lT_M-IX9qpqRE</recordid><startdate>20020901</startdate><enddate>20020901</enddate><creator>Li, Xin-Min</creator><creator>Momsen, Maureen M.</creator><creator>Brockman, Howard L.</creator><creator>Brown, Rhoderick E.</creator><general>Elsevier Inc</general><general>Biophysical Society</general><scope>6I.</scope><scope>AAFTH</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>3V.</scope><scope>7QO</scope><scope>7QP</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>7X2</scope><scope>7X7</scope><scope>7XB</scope><scope>88A</scope><scope>88E</scope><scope>88I</scope><scope>8AF</scope><scope>8AO</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8G5</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>ARAPS</scope><scope>ATCPS</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>LK8</scope><scope>M0K</scope><scope>M0S</scope><scope>M1P</scope><scope>M2O</scope><scope>M2P</scope><scope>M7P</scope><scope>MBDVC</scope><scope>P5Z</scope><scope>P62</scope><scope>P64</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>S0X</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20020901</creationdate><title>Lactosylceramide: Effect of Acyl Chain Structure on Phase Behavior and Molecular Packing</title><author>Li, Xin-Min ; Momsen, Maureen M. ; Brockman, Howard L. ; Brown, Rhoderick E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c556t-666d7700b7fb6c84b2bebf7bf33262b0fffc0e3f16effd8f793a876b5db8c9533</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Antigens, CD - chemistry</topic><topic>Binding Sites</topic><topic>Biophysical Phenomena</topic><topic>Biophysics</topic><topic>Calorimetry, Differential Scanning</topic><topic>Carbohydrates - chemistry</topic><topic>Galactosylceramides - chemistry</topic><topic>Lactosylceramides - chemistry</topic><topic>Lipids</topic><topic>Lipids - chemistry</topic><topic>Metabolism</topic><topic>Molecular biology</topic><topic>Sphingomyelins - chemistry</topic><topic>Temperature</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Xin-Min</creatorcontrib><creatorcontrib>Momsen, Maureen M.</creatorcontrib><creatorcontrib>Brockman, Howard L.</creatorcontrib><creatorcontrib>Brown, Rhoderick E.</creatorcontrib><collection>ScienceDirect Open Access Titles</collection><collection>Elsevier:ScienceDirect:Open Access</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Biotechnology Research Abstracts</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Agricultural Science Collection</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Biology Database (Alumni Edition)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Science Database (Alumni Edition)</collection><collection>STEM Database</collection><collection>ProQuest Pharma Collection</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Research Library (Alumni Edition)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>Advanced Technologies & Aerospace Collection</collection><collection>Agricultural & Environmental Science Collection</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>Natural Science Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Engineering Research Database</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>Research Library Prep</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>ProQuest Biological Science Collection</collection><collection>Agricultural Science Database</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Research Library</collection><collection>Science Database</collection><collection>Biological Science Database</collection><collection>Research Library (Corporate)</collection><collection>Advanced Technologies & Aerospace Database</collection><collection>ProQuest Advanced Technologies & Aerospace Collection</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>ProQuest Central Basic</collection><collection>SIRS Editorial</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Biophysical journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Xin-Min</au><au>Momsen, Maureen M.</au><au>Brockman, Howard L.</au><au>Brown, Rhoderick E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Lactosylceramide: Effect of Acyl Chain Structure on Phase Behavior and Molecular Packing</atitle><jtitle>Biophysical journal</jtitle><addtitle>Biophys J</addtitle><date>2002-09-01</date><risdate>2002</risdate><volume>83</volume><issue>3</issue><spage>1535</spage><epage>1546</epage><pages>1535-1546</pages><issn>0006-3495</issn><eissn>1542-0086</eissn><abstract>Lactosylceramide (LacCer) is a pivotal intermediate in the metabolism of higher gangliosides, localizes to sphingolipid-sterol “rafts,” and has been implicated in cellular signaling. To provide a fundamental characterization of LacCer phase behavior and intermolecular packing, LacCer containing different saturated (16:0, 18:0, 24:0) or monounsaturated (18:1
Δ9, 24:1
Δ15) acyl chains were synthesized and studied by differential scanning calorimetry and Langmuir film balance approaches. Compared to related sphingoid- and glycerol-based lipids, LacCers containing saturated acyl chains display relatively high thermotropic and pressure-induced transitions. LacCer monolayer films are less elastic in an in-plane sense than sphingomyelin films, but are somewhat more elastic than galactosylceramide films. Together, these findings indicate that the disaccharide headgroup only marginally disrupts gel phase packing and orients more perpendicular than parallel to the interface. This contrasts the reported behavior of digalactosyldiglycerides with saturated acyl chains. Introducing single
cis double bonds into the LacCer acyl chains dramatically lowers the high thermotropic and pressure-induced transitions. Greater reductions occur when
cis double bonds are located near the middle of the acyl chains. The results are discussed in terms of how an extended disaccharide headgroup can enhance interactions among naturally abundant LacCers with saturated acyl chains.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>12202378</pmid><doi>10.1016/S0006-3495(02)73923-4</doi><tpages>12</tpages><oa>free_for_read</oa></addata></record> |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete; Cell Press Free Archives; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central |
| subjects | Antigens, CD - chemistry Binding Sites Biophysical Phenomena Biophysics Calorimetry, Differential Scanning Carbohydrates - chemistry Galactosylceramides - chemistry Lactosylceramides - chemistry Lipids Lipids - chemistry Metabolism Molecular biology Sphingomyelins - chemistry Temperature |
| title | Lactosylceramide: Effect of Acyl Chain Structure on Phase Behavior and Molecular Packing |
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