SM(d18:1/16:0) (BioDeep_00000018566)
human metabolite Endogenous blood metabolite
代谢物信息卡片
化学式: C39H79N2O6P (702.5675444000001)
中文名称: N-棕榈酰-D-鞘磷脂
谱图信息:
最多检出来源 Homo sapiens(blood) 4.47%
Last reviewed on 2024-09-14.
Cite this Page
SM(d18:1/16:0). BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/palmitoyl_sphingomyelin_(d18:1_16:0) (retrieved
2024-11-23) (BioDeep RN: BioDeep_00000018566). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
分子结构信息
SMILES: CCCCCCCCCCCCCC=CC(O)C(COP(=O)([O-])OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCCCCCC
InChI: InChI=1S/C39H79N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-38(42)37(36-47-48(44,45)46-35-34-41(3,4)5)40-39(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h30,32,37-38,42H,6-29,31,33-36H2,1-5H3,(H-,40,43,44,45)/b32-30+/t37-,38+/m0/s1
描述信息
Sphingomyelin (d18:1/16:0) or SM(d18:1/16:0) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. It usually consists of phosphorylcholine and ceramide. SM(d18:1/16:0) consists of a sphingosine backbone and a palmitic acid chain. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SM has a ceramide core (sphingosine bonded to a fatty acid via an amide linkage). In addition, it contains one polar head group, which is either phosphocholine or phosphoethanolamine. The plasma membrane of cells is highly enriched in sphingomyelin and is considered largely to be found in the exoplasmic leaflet of the cell membrane. However, there is some evidence that there may also be a sphingomyelin pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2, an enzyme that breaks down sphingomyelin into ceramide, has been found to localize exclusively to the inner leaflet further suggesting that there may be sphingomyelin present there. Sphingomyelin can accumulate in a rare hereditary disease called Niemann-Pick Disease, types A and B. Niemann-Pick disease is a genetically-inherited disease caused by a deficiency in the enzyme sphingomyelinase, which causes the accumulation of sphingomyelin in spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage. SMs play a role in signal transduction. Sphingomyelins are synthesized by the transfer of phosphorylcholine from phosphatidylcholine to a ceramide in a reaction catalyzed by sphingomyelin synthase.
Sphingomyelin (d18:1/16:0) or SM(d18:1/16:0) is a sphingomyelin. Sphingomyelin (SM or SPH) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. It usually consists of phosphorylcholine and ceramide. SM(18:1/16:0) consists of oleic acid attached to the C1 position and palmitic acid attached to the C2 position. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SPH has a ceramide core (sphingosine bonded to a fatty acid via an amide linkage). In addition it contains one polar head group, which is either phosphocholine or phosphoethanolamine. The plasma membrane of cells is highly enriched in sphingomyelin and is considered largely to be found in the exoplasmic leaflet of the cell membrane. However, there is some evidence that there may also be a sphingomyelin pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down sphingomyelin into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be sphingomyelin present there. Sphingomyelin can accumulate in a rare hereditary disease called Niemann-Pick Disease, types A and B. Niemann-Pick disease is a genetically-inherited disease caused by a deficiency in the enzyme Sphingomyelinase, which causes the accumulation of Sphingomyelin in spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage. SMs play a role in signal transduction.
同义名列表
40 个代谢物同义名
(2S,3R,4E)-3-Hydroxy-2-(palmitoylamino)octadec-4-en-1-yl 2-(trimethylazaniumyl)ethyl phosphoric acid; (2S,3R,4E)-2-(Palmitoylamino)-3-hydroxyoctadec-4-en-1-yl 2-(trimethylazaniumyl)ethyl phosphoric acid; (2-{[(2S,3R,4E)-2-hexadecanamido-3-hydroxyoctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium; (2S,3R,4E)-3-Hydroxy-2-(palmitoylamino)octadec-4-en-1-yl 2-(trimethylazaniumyl)ethyl phosphate; (2S,3R,4E)-2-(Palmitoylamino)-3-hydroxyoctadec-4-en-1-yl 2-(trimethylazaniumyl)ethyl phosphate; N-(Hexadecanoyl)-1-phosphocholine-D-erythro-sphingosine; N-(Hexadecanoyl)-1-phosphocholine-erythro-4-sphingenine; N-Palmitoyl-D-erythro-sphingosylphosphorylcholine; N-(Hexadecanoyl)-1-phosphocholine-sphing-4-enine; N-(hexadecanoyl)-sphing-4-enine-1-phosphocholine; N-Palmitoyl-D-erythrosphingosylphosphorylcholine; N-(Hexadecanoyl)-1-phosphocholine-4-sphingenine; N-(Hexadecanoyl)-1-phosphocholine-D-sphingosine; N-(Hexadecanoyl)-1-phosphocholine-sphingenine; N-Hexadecanoylsphing-4-enine-1-phosphocholine; N-(Hexadecanoyl)-1-phosphocholine-sphingosine; N-Palmitoylsphing-4-enine-1-phosphocholine; N-Palmitoylsphingosine-phosphorylcholine; N-Palmitoylsphingosine-1-phosphocholine; N-Palmitoylsphingosylphosphorylcholine; Palmitoyl sphingomyelin (D18:1/16:0); Sphingomyelin (DC18:1/c16:0); N-Hexadecanoylsphingomyelin; Sphingomyelin (D18:1 C16:0); N-Palmitoyl-D-sphingomyelin; Sphingomyelin (D18:1/16:0); Hexadecanoyl sphingomyelin; Sphingomyelin(D18:1/16:0); Sphingomyelin D18:1/16:0; N-Palmitoylsphingomyelin; Palmitoyl sphingomyelin; Palmitoylsphingomyelin; Sphingomyelin 16:0; C16-Sphingomyelin; C16 Sphingomyelin; SM(d18:1/16:0); SM(18:1/16:0); SCHEMBL195823; sphingomyelin; N-PSPC
数据库引用编号
10 个数据库交叉引用编号
- ChEBI: CHEBI:78646
- PubChem: 53394029
- PubChem: 9939941
- HMDB: HMDB0010169
- ChEMBL: CHEMBL4526394
- MetaCyc: CPD66-42
- foodb: FDB027352
- chemspider: 8115562
- CAS: 6254-89-3
- PMhub: MS000009072
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
2 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(2)
- Sphingolipid metabolism (integrated pathway):
Palmitoyl-CoA ⟶ 3-keto-sphinganine
- Sphingolipid metabolism: integrated pathway:
Palmitoyl-CoA ⟶ 3-keto-sphinganine
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
2 个相关的物种来源信息
- 9606 - Homo sapiens: -
- 5691 - Trypanosoma brucei: 10.1371/JOURNAL.PNTD.0001618
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。
文献列表
- Pratibha Kumari, Hemant K Kashyap. DMSO induced dehydration of heterogeneous lipid bilayers and its impact on their structures.
The Journal of chemical physics.
2019 Dec; 151(21):215103. doi:
10.1063/1.5127852
. [PMID: 31822068] - Pratibha Kumari, Monika Kumari, Hemant K Kashyap. Counter-effects of Ethanol and Cholesterol on the Heterogeneous PSM-POPC Lipid Membrane: A Molecular Dynamics Simulation Study.
The journal of physical chemistry. B.
2019 11; 123(45):9616-9628. doi:
10.1021/acs.jpcb.9b07107
. [PMID: 31625744] - Amy K Smith, Dmitri K Klimov. Molecular Dynamics Investigation of the Ternary Bilayer Formed by Saturated Phosphotidylcholine, Sphingomyelin, and Cholesterol.
The journal of physical chemistry. B.
2018 12; 122(49):11311-11325. doi:
10.1021/acs.jpcb.8b07256
. [PMID: 30156415] - Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics.
Scientific reports.
2018 07; 8(1):10056. doi:
10.1038/s41598-018-28477-9
. [PMID: 29968805] - Zoran Arsov, Emilio J González-Ramírez, Felix M Goñi, Stephanie Tristram-Nagle, John F Nagle. Phase behavior of palmitoyl and egg sphingomyelin.
Chemistry and physics of lipids.
2018 07; 213(?):102-110. doi:
10.1016/j.chemphyslip.2018.03.003
. [PMID: 29689259] - Jeffrey Michael Breidigan, Natalie Krzyzanowski, Yangmingyue Liu, Lionel Porcar, Ursula Perez-Salas. Influence of the membrane environment on cholesterol transfer.
Journal of lipid research.
2017 12; 58(12):2255-2263. doi:
10.1194/jlr.m077909
. [PMID: 29046341] - Eileen Edler, Eric Schulze, Matthias Stein. Membrane localization and dynamics of geranylgeranylated Rab5 hypervariable region.
Biochimica et biophysica acta. Biomembranes.
2017 Aug; 1859(8):1335-1349. doi:
10.1016/j.bbamem.2017.04.021
. [PMID: 28455099] - T R Galimzyanov, A S Lyushnyak, V V Aleksandrova, L A Shilova, I I Mikhalyov, I M Molotkovskaya, S A Akimov, O V Batishchev. Line Activity of Ganglioside GM1 Regulates the Raft Size Distribution in a Cholesterol-Dependent Manner.
Langmuir : the ACS journal of surfaces and colloids.
2017 04; 33(14):3517-3524. doi:
10.1021/acs.langmuir.7b00404
. [PMID: 28324651] - Matthew Patterson, Hans J Vogel, Elmar J Prenner. The effect of repeated lateral compression and expansions mimicking blinking on selected tear film polar lipid monofilms.
Biochimica et biophysica acta. Biomembranes.
2017 03; 1859(3):319-330. doi:
10.1016/j.bbamem.2016.12.010
. [PMID: 27993563] - Juan Palacios-Ortega, Sara García-Linares, Mia Åstrand, Md Abdullah Al Sazzad, José G Gavilanes, Álvaro Martínez-del-Pozo, J Peter Slotte. Regulation of Sticholysin II-Induced Pore Formation by Lipid Bilayer Composition, Phase State, and Interfacial Properties.
Langmuir : the ACS journal of surfaces and colloids.
2016 Apr; 32(14):3476-84. doi:
10.1021/acs.langmuir.6b00082
. [PMID: 27003246] - Jumin Lee, Xi Cheng, Jason M Swails, Min Sun Yeom, Peter K Eastman, Justin A Lemkul, Shuai Wei, Joshua Buckner, Jong Cheol Jeong, Yifei Qi, Sunhwan Jo, Vijay S Pande, David A Case, Charles L Brooks, Alexander D MacKerell, Jeffery B Klauda, Wonpil Im. CHARMM-GUI Input Generator for NAMD, GROMACS, AMBER, OpenMM, and CHARMM/OpenMM Simulations Using the CHARMM36 Additive Force Field.
Journal of chemical theory and computation.
2016 Jan; 12(1):405-13. doi:
10.1021/acs.jctc.5b00935
. [PMID: 26631602] - Seiichi Sakamoto, Takuhiro Uto, Yukihiro Shoyama. Effect of glycyrrhetinic acid on lipid raft model at the air/water interface.
Biochimica et biophysica acta.
2015 Feb; 1848(2):434-43. doi:
10.1016/j.bbamem.2014.11.014
. [PMID: 25445675] - Richard M Venable, Alexander J Sodt, Brent Rogaski, Huan Rui, Elizabeth Hatcher, Alexander D MacKerell, Richard W Pastor, Jeffery B Klauda. CHARMM all-atom additive force field for sphingomyelin: elucidation of hydrogen bonding and of positive curvature.
Biophysical journal.
2014 Jul; 107(1):134-45. doi:
10.1016/j.bpj.2014.05.034
. [PMID: 24988348] - Yanbo Yang, Takashi Kuwano, William R Lagor, Carolyn J Albert, Siobhan Brenton, Daniel J Rader, David A Ford, Robert J Brown. Lipidomic analyses of female mice lacking hepatic lipase and endothelial lipase indicate selective modulation of plasma lipid species.
Lipids.
2014 Jun; 49(6):505-15. doi:
10.1007/s11745-014-3907-6
. [PMID: 24777581] - Peter J Quinn. Structure of sphingomyelin bilayers and complexes with cholesterol forming membrane rafts.
Langmuir : the ACS journal of surfaces and colloids.
2013 Jul; 29(30):9447-56. doi:
10.1021/la4018129
. [PMID: 23863113] - Christian Sergelius, Shou Yamaguchi, Tetsuya Yamamoto, Oskar Engberg, Shigeo Katsumura, J Peter Slotte. Cholesterol's interactions with serine phospholipids - a comparison of N-palmitoyl ceramide phosphoserine with dipalmitoyl phosphatidylserine.
Biochimica et biophysica acta.
2013 Feb; 1828(2):785-91. doi:
10.1016/j.bbamem.2012.11.009
. [PMID: 23159809] - Christopher M Depner, Maret G Traber, Gerd Bobe, Elizabeth Kensicki, Kurt M Bohren, Ginger Milne, Donald B Jump. A metabolomic analysis of omega-3 fatty acid-mediated attenuation of western diet-induced nonalcoholic steatohepatitis in LDLR-/- mice.
PloS one.
2013; 8(12):e83756. doi:
10.1371/journal.pone.0083756
. [PMID: 24358308] - Joanna M Kwiatek, Dylan M Owen, Ahmed Abu-Siniyeh, Ping Yan, Leslie M Loew, Katharina Gaus. Characterization of a new series of fluorescent probes for imaging membrane order.
PloS one.
2013; 8(2):e52960. doi:
10.1371/journal.pone.0052960
. [PMID: 23390489] - Sherry S W Leung, Jon V Busto, Amir Keyvanloo, Félix M Goñi, Jenifer Thewalt. Insights into sphingolipid miscibility: separate observation of sphingomyelin and ceramide N-acyl chain melting.
Biophysical journal.
2012 Dec; 103(12):2465-74. doi:
10.1016/j.bpj.2012.10.041
. [PMID: 23260048] - Anirban Polley, Satyavani Vemparala, Madan Rao. Atomistic simulations of a multicomponent asymmetric lipid bilayer.
The journal of physical chemistry. B.
2012 Nov; 116(45):13403-10. doi:
10.1021/jp3032868
. [PMID: 23088327] - Terhi Maula, Ibai Artetxe, Pia-Maria Grandell, J Peter Slotte. Importance of the sphingoid base length for the membrane properties of ceramides.
Biophysical journal.
2012 Nov; 103(9):1870-9. doi:
10.1016/j.bpj.2012.09.018
. [PMID: 23199915] - Irina V Ionova, Vsevolod A Livshits, Derek Marsh. Phase diagram of ternary cholesterol/palmitoylsphingomyelin/palmitoyloleoyl-phosphatidylcholine mixtures: spin-label EPR study of lipid-raft formation.
Biophysical journal.
2012 Apr; 102(8):1856-65. doi:
10.1016/j.bpj.2012.03.043
. [PMID: 22768941] - Tong Wang, Hidehiko Shogomori, Masahiko Hara, Taro Yamada, Toshihide Kobayashi. Nanomechanical recognition of sphingomyelin-rich membrane domains by atomic force microscopy.
Biochemistry.
2012 Jan; 51(1):74-82. doi:
10.1021/bi2011652
. [PMID: 22148674] - Hiroaki Saito, Wataru Shinoda. Cholesterol effect on water permeability through DPPC and PSM lipid bilayers: a molecular dynamics study.
The journal of physical chemistry. B.
2011 Dec; 115(51):15241-50. doi:
10.1021/jp201611p
. [PMID: 22081997] - Lucia Becucci, Federica Scaletti, Rolando Guidelli. Gel-phase microdomains and lipid rafts in monolayers affect the redox properties of ubiquinone-10.
Biophysical journal.
2011 Jul; 101(1):134-43. doi:
10.1016/j.bpj.2011.05.051
. [PMID: 21723823] - Thomas K M Nyholm, Daniel Lindroos, Bodil Westerlund, J Peter Slotte. Construction of a DOPC/PSM/cholesterol phase diagram based on the fluorescence properties of trans-parinaric acid.
Langmuir : the ACS journal of surfaces and colloids.
2011 Jul; 27(13):8339-50. doi:
10.1021/la201427w
. [PMID: 21627141] - Lucia Becucci, Elisabetta Lottini, Rolando Guidelli. Influence of gel-phase microdomains and lipid rafts in lipid monolayers on the electron transfer of a lipophilic redox probe: dioctadecylviologen.
Physical chemistry chemical physics : PCCP.
2011 Mar; 13(9):3917-24. doi:
10.1039/c0cp01928c
. [PMID: 21210041] - Paul W Tumaneng, Sagar A Pandit, Guijun Zhao, H L Scott. Self-consistent mean-field model for palmitoyloleoylphosphatidylcholine-palmitoyl sphingomyelin-cholesterol lipid bilayers.
Physical review. E, Statistical, nonlinear, and soft matter physics.
2011 Mar; 83(3 Pt 1):031925. doi:
10.1103/physreve.83.031925
. [PMID: 21517541] - Lorant Janosi, Alemayehu Gorfe. Importance of the sphingosine base double-bond geometry for the structural and thermodynamic properties of sphingomyelin bilayers.
Biophysical journal.
2010 Nov; 99(9):2957-66. doi:
10.1016/j.bpj.2010.09.020
. [PMID: 21044593] - Shidong Chu, Sergey Maltsev, A-H Emwas, Gary A Lorigan. Solid-state NMR paramagnetic relaxation enhancement immersion depth studies in phospholipid bilayers.
Journal of magnetic resonance (San Diego, Calif. : 1997).
2010 Nov; 207(1):89-94. doi:
10.1016/j.jmr.2010.08.012
. [PMID: 20851650] - Bodil Westerlund, Pia-Maria Grandell, Y Jenny E Isaksson, J Peter Slotte. Ceramide acyl chain length markedly influences miscibility with palmitoyl sphingomyelin in bilayer membranes.
European biophysics journal : EBJ.
2010 Jul; 39(8):1117-28. doi:
10.1007/s00249-009-0562-6
. [PMID: 19908035] - Jon V Busto, María Laura Fanani, Luisina De Tullio, Jesús Sot, Bruno Maggio, Félix M Goñi, Alicia Alonso. Coexistence of immiscible mixtures of palmitoylsphingomyelin and palmitoylceramide in monolayers and bilayers.
Biophysical journal.
2009 Nov; 97(10):2717-26. doi:
10.1016/j.bpj.2009.08.040
. [PMID: 19917225] - Robert Vácha, Max L Berkowitz, Pavel Jungwirth. Molecular model of a cell plasma membrane with an asymmetric multicomponent composition: water permeation and ion effects.
Biophysical journal.
2009 Jun; 96(11):4493-501. doi:
10.1016/j.bpj.2009.03.010
. [PMID: 19486672] - Liana C Silva, Anthony H Futerman, Manuel Prieto. Lipid raft composition modulates sphingomyelinase activity and ceramide-induced membrane physical alterations.
Biophysical journal.
2009 Apr; 96(8):3210-22. doi:
10.1016/j.bpj.2008.12.3923
. [PMID: 19383465] - Tim Bartels, Ravi S Lankalapalli, Robert Bittman, Klaus Beyer, Michael F Brown. Raftlike mixtures of sphingomyelin and cholesterol investigated by solid-state 2H NMR spectroscopy.
Journal of the American Chemical Society.
2008 Nov; 130(44):14521-32. doi:
10.1021/ja801789t
. [PMID: 18839945] - Katrin K Halling, Bodil Ramstedt, Joel H Nyström, J Peter Slotte, Thomas K M Nyholm. Cholesterol interactions with fluid-phase phospholipids: effect on the lateral organization of the bilayer.
Biophysical journal.
2008 Oct; 95(8):3861-71. doi:
10.1529/biophysj.108.133744
. [PMID: 18641061] - Y J E Björkqvist, S Nybond, T K M Nyholm, J P Slotte, B Ramstedt. N-palmitoyl-sulfatide participates in lateral domain formation in complex lipid bilayers.
Biochimica et biophysica acta.
2008 Apr; 1778(4):954-62. doi:
10.1016/j.bbamem.2007.12.016
. [PMID: 18206111] - Jussi Aittoniemi, Perttu S Niemelä, Marja T Hyvönen, Mikko Karttunen, Ilpo Vattulainen. Insight into the putative specific interactions between cholesterol, sphingomyelin, and palmitoyl-oleoyl phosphatidylcholine.
Biophysical journal.
2007 Feb; 92(4):1125-37. doi:
10.1529/biophysj.106.088427
. [PMID: 17114220] - Thomas Mehnert, Kochurani Jacob, Robert Bittman, Klaus Beyer. Structure and lipid interaction of N-palmitoylsphingomyelin in bilayer membranes as revealed by 2H-NMR spectroscopy.
Biophysical journal.
2006 Feb; 90(3):939-46. doi:
10.1529/biophysj.105.063271
. [PMID: 16284259] - Sarah L Veatch, Sarah L Keller. Miscibility phase diagrams of giant vesicles containing sphingomyelin.
Physical review letters.
2005 Apr; 94(14):148101. doi:
10.1103/physrevlett.94.148101
. [PMID: 15904115] - M Isabel Collado, Félix M Goñi, Alicia Alonso, Derek Marsh. Domain formation in sphingomyelin/cholesterol mixed membranes studied by spin-label electron spin resonance spectroscopy.
Biochemistry.
2005 Mar; 44(12):4911-8. doi:
10.1021/bi0474970
. [PMID: 15779918] - Rodrigo F M de Almeida, Luís M S Loura, Alexander Fedorov, Manuel Prieto. Lipid rafts have different sizes depending on membrane composition: a time-resolved fluorescence resonance energy transfer study.
Journal of molecular biology.
2005 Mar; 346(4):1109-20. doi:
10.1016/j.jmb.2004.12.026
. [PMID: 15701521] - Katrin K Halling, J Peter Slotte. Membrane properties of plant sterols in phospholipid bilayers as determined by differential scanning calorimetry, resonance energy transfer and detergent-induced solubilization.
Biochimica et biophysica acta.
2004 Aug; 1664(2):161-71. doi:
10.1016/j.bbamem.2004.05.006
. [PMID: 15328048] - Rodrigo F M de Almeida, Aleksandre Fedorov, Manuel Prieto. Sphingomyelin/phosphatidylcholine/cholesterol phase diagram: boundaries and composition of lipid rafts.
Biophysical journal.
2003 Oct; 85(4):2406-16. doi:
10.1016/s0006-3495(03)74664-5
. [PMID: 14507704] - Enrico Mombelli, Roger Morris, William Taylor, Franca Fraternali. Hydrogen-bonding propensities of sphingomyelin in solution and in a bilayer assembly: a molecular dynamics study.
Biophysical journal.
2003 Mar; 84(3):1507-17. doi:
10.1016/s0006-3495(03)74963-7
. [PMID: 12609857] - J N Maiorano, W S Davidson. The orientation of helix 4 in apolipoprotein A-I-containing reconstituted high density lipoproteins.
The Journal of biological chemistry.
2000 Jun; 275(23):17374-80. doi:
10.1074/jbc.m000044200
. [PMID: 10751383] - P R Maulik, G G Shipley. N-palmitoyl sphingomyelin bilayers: structure and interactions with cholesterol and dipalmitoylphosphatidylcholine.
Biochemistry.
1996 Jun; 35(24):8025-34. doi:
10.1021/bi9528356
. [PMID: 8672507] - J B Speyer, P K Sripada, S K Das Gupta, G G Shipley, R G Griffin. Magnetic orientation of sphingomyelin-lecithin bilayers.
Biophysical journal.
1987 Apr; 51(4):687-91. doi:
10.1016/s0006-3495(87)83394-5
. [PMID: 3580492] - B R Lentz, M Hoechli, Y Barenholz. Acyl chain order and lateral domain formation in mixed phosphatidylcholine--sphingomyelin multilamellar and unilamellar vesicles.
Biochemistry.
1981 Nov; 20(24):6803-9. doi:
10.1021/bi00527a010
. [PMID: 7317355]