메뉴 건너뛰기




Volumn 51, Issue 1, 2010, Pages 42-52

Synthesis, calorimetric studies, and crystal structures of N, O-diacylethanolamines with matched chains

Author keywords

Bilayer structure; Chain packing; Differential scanning calorimetry; Ethanolamine; Hydrogen bonding; Single crystal X ray diffraction

Indexed keywords

DIDECANOYLETHANOLAMINE; DILAUROYLETHANOLAMINE; DIMYRISTOYLETHANOLAMINE; ETHANOLAMINE; PHOSPHATIDYLETHANOLAMINE; UNCLASSIFIED DRUG;

EID: 73149121906     PISSN: 00222275     EISSN: 15397262     Source Type: Journal    
DOI: 10.1194/jlr.M900105-JLR200     Document Type: Article
Times cited : (29)

References (47)
  • 1
    • 73149106766 scopus 로고
    • Biological synthesis of choline by rats on diets with and without adequate lipotropic methyl
    • Stetten, D., Jr. 1941. Biological synthesis of choline by rats on diets with and without adequate lipotropic methyl. J. Biol. Chem. 142: 629-633.
    • (1941) J. Biol. Chem , vol.142 , pp. 629-633
    • Stetten Jr., D.1
  • 2
    • 0017183774 scopus 로고
    • Synthesis of choline from ethanolamine in rat brain
    • Kewitz, H., and O. Pleul. 1976. Synthesis of choline from ethanolamine in rat brain. Proc. Natl. Acad. Sci. USA. 73: 2181-2185.
    • (1976) Proc. Natl. Acad. Sci. USA , vol.73 , pp. 2181-2185
    • Kewitz, H.1    Pleul, O.2
  • 3
    • 0025676296 scopus 로고
    • N-Acylated glycerophospholipids and their derivatives
    • Schmid, H. H. O., P. C. Schmid, and V. Natarajan. 1990. N-Acylated glycerophospholipids and their derivatives. Prog. Lipid Res. 29: 1-43.
    • (1990) Prog. Lipid Res , vol.29 , pp. 1-43
    • Schmid, H.H.O.1    Schmid, P.C.2    Natarajan, V.3
  • 4
    • 3242703446 scopus 로고    scopus 로고
    • Occurrence, metabolism, and prospective functions of N-acylethanolamines in plants
    • Chapman, K. D. 2004. Occurrence, metabolism, and prospective functions of N-acylethanolamines in plants. Prog. Lipid Res. 43: 302-327.
    • (2004) Prog. Lipid Res , vol.43 , pp. 302-327
    • Chapman, K.D.1
  • 6
    • 0027982533 scopus 로고
    • Anandamide (arachidonylethanolamide), a brain cannabinoid receptor agonist, reduces sperm fertilizing capacity in sea urchins by inhibiting the acrosome reaction
    • Schuel, H., E. Goldstein, R. Mechoulam, A. M. Zimmerman, and S. Zimmerman. 1994. Anandamide (arachidonylethanolamide), a brain cannabinoid receptor agonist, reduces sperm fertilizing capacity in sea urchins by inhibiting the acrosome reaction. Proc. Natl. Acad. Sci. USA. 91: 7678-7682.
    • (1994) Proc. Natl. Acad. Sci. USA , vol.91 , pp. 7678-7682
    • Schuel, H.1    Goldstein, E.2    Mechoulam, R.3    Zimmerman, A.M.4    Zimmerman, S.5
  • 7
    • 0029154145 scopus 로고
    • Inhibition of anandamide of gap junctions and intercellular calcium signaling in striatal astrocytes
    • Venance, L., D. Piomelli, J. Glowinski, and C. Giaume. 1995. Inhibition of anandamide of gap junctions and intercellular calcium signaling in striatal astrocytes. Nature. 376: 590-594.
    • (1995) Nature , vol.376 , pp. 590-594
    • Venance, L.1    Piomelli, D.2    Glowinski, J.3    Giaume, C.4
  • 8
    • 0028906566 scopus 로고
    • Mast cells express a peripheral cannabinoid receptor with differential sensitivity to anandamide and palmitoylethanolamide
    • Facci, L., R. Dal Toso, S. Romanello, A. Buriani, S. D. Skaper, and A. Leon. 1995. Mast cells express a peripheral cannabinoid receptor with differential sensitivity to anandamide and palmitoylethanolamide. Proc. Natl. Acad. Sci. USA. 92: 3376-3380.
    • (1995) Proc. Natl. Acad. Sci. USA , vol.92 , pp. 3376-3380
    • Facci, L.1    Dal Toso, R.2    Romanello, S.3    Buriani, A.4    Skaper, S.D.5    Leon, A.6
  • 9
    • 0000821035 scopus 로고    scopus 로고
    • N-Acylethanolamines: Formation and molecular composition of a new class of plant lipids
    • Chapman, K. D., S. Tripathy, B. Venables, and A. D. Desouja. 1998. N-Acylethanolamines: formation and molecular composition of a new class of plant lipids. Plant Physiol. 116: 1163-1168.
    • (1998) Plant Physiol , vol.116 , pp. 1163-1168
    • Chapman, K.D.1    Tripathy, S.2    Venables, B.3    Desouja, A.D.4
  • 10
    • 0002456314 scopus 로고
    • A phosphorus magnetic resonance and a differential scanning calorimetry study of the physical properties of N-acylphosphatidylethanolamines in aqueous dispersions
    • Akoka, S., C. Tellier, C. LeRoux, and D. Marion. 1988. A phosphorus magnetic resonance and a differential scanning calorimetry study of the physical properties of N-acylphosphatidylethanolamines in aqueous dispersions. Chem. Phys. Lipids. 46: 43-50.
    • (1988) Chem. Phys. Lipids , vol.46 , pp. 43-50
    • Akoka, S.1    Tellier, C.2    LeRoux, C.3    Marion, D.4
  • 11
    • 0025297966 scopus 로고
    • Study of the structure of N-acyldipalmitoylphosphatidylethanolamines in aqueous dispersion by infrared and Raman spectroscopies
    • LaFrance, D., D. Marion, and M. Pézolet. 1990. Study of the structure of N-acyldipalmitoylphosphatidylethanolamines in aqueous dispersion by infrared and Raman spectroscopies. Biochemistry. 29: 4592-4599.
    • (1990) Biochemistry , vol.29 , pp. 4592-4599
    • LaFrance, D.1    Marion, D.2    Pézolet, M.3
  • 12
    • 0030862278 scopus 로고    scopus 로고
    • Differential scanning calorimetry of chain-melting phase transitions of N-acylphosphatidylethanolamines
    • Swamy, M. J., D. Marsh, and M. Ramakrishnan. 1997. Differential scanning calorimetry of chain-melting phase transitions of N-acylphosphatidylethanolamines. Biophys. J. 73: 2556-2564.
    • (1997) Biophys. J , vol.73 , pp. 2556-2564
    • Swamy, M.J.1    Marsh, D.2    Ramakrishnan, M.3
  • 13
    • 0030703130 scopus 로고    scopus 로고
    • Differential scanning calorimetric studies on the thermotropic phase transitions of dry and hydrated forms of N-acylethanolamines of even chainlengths
    • Ramakrishnan, M., V. Sheeba, S. S. Komath, and M. J. Swamy. 1997. Differential scanning calorimetric studies on the thermotropic phase transitions of dry and hydrated forms of N-acylethanolamines of even chainlengths. Biochim. Biophys. Acta. 1329: 302-310.
    • (1997) Biochim. Biophys. Acta , vol.1329 , pp. 302-310
    • Ramakrishnan, M.1    Sheeba, V.2    Komath, S.S.3    Swamy, M.J.4
  • 14
    • 0037039596 scopus 로고    scopus 로고
    • N-Myristoylated phosphatidylethanolamine: Interfacial behavior and interaction with cholesterol
    • Li, X-M., M. Ramakrishnan, H. L. Brockman, R. E. Brown, and M. J. Swamy. 2002. N-Myristoylated phosphatidylethanolamine: interfacial behavior and interaction with cholesterol. Langmuir. 18: 231-238.
    • (2002) Langmuir , vol.18 , pp. 231-238
    • Li, X.-M.1    Ramakrishnan, M.2    Brockman, H.L.3    Brown, R.E.4    Swamy, M.J.5
  • 15
    • 34250350051 scopus 로고    scopus 로고
    • Miscibility and phase behavior of N-acylethanolamine/ diacylphosphatidylethanolamine binary mixtures of matched acyl chainlengths (N=14, 16)
    • Kamlekar, R. K., S. Satyanarayana, D. Marsh, and M. J. Swamy. 2007. Miscibility and phase behavior of N-acylethanolamine/ diacylphosphatidylethanolamine binary mixtures of matched acyl chainlengths (N=14, 16). Biophys. J. 92: 3968-3977.
    • (2007) Biophys. J , vol.92 , pp. 3968-3977
    • Kamlekar, R.K.1    Satyanarayana, S.2    Marsh, D.3    Swamy, M.J.4
  • 16
    • 0037032429 scopus 로고    scopus 로고
    • N-Myristoylethanolamine - cholesterol (1:1) complex: First evidence from differential scanning calorimetry, fast-atom-bombardment mass spectrometry and computational modeling
    • Ramakrishnan, M., R. Kenoth, K. Ravikanth, M. S. Chandra, T. P. Radhakrishnan, and M. J. Swamy. 2002. N-Myristoylethanolamine - cholesterol (1:1) complex: first evidence from differential scanning calorimetry, fast-atom-bombardment mass spectrometry and computational modeling. FEBS Lett. 531: 343-347.
    • (2002) FEBS Lett , vol.531 , pp. 343-347
    • Ramakrishnan, M.1    Kenoth, R.2    Ravikanth, K.3    Chandra, M.S.4    Radhakrishnan, T.P.5    Swamy, M.J.6
  • 17
    • 56449107340 scopus 로고    scopus 로고
    • Interaction of N-myristoylethanolamine with cholesterol investigated in a Langmuir film at the air-water interface
    • Kamlekar, R. K., M. S. Chandra, T. P. Radhakrishnan, and M. J. Swamy. 2009. Interaction of N-myristoylethanolamine with cholesterol investigated in a Langmuir film at the air-water interface. Biophys. Chem. 139: 63-69.
    • (2009) Biophys. Chem , vol.139 , pp. 63-69
    • Kamlekar, R.K.1    Chandra, M.S.2    Radhakrishnan, T.P.3    Swamy, M.J.4
  • 18
    • 0642276218 scopus 로고    scopus 로고
    • Miscibility and phase behaviour of binary mixtures of N-palmitoylethanolamine and dipalmitoylphosphatidylcholine
    • Swamy, M. J., M. Ramakrishnan, D. Marsh, and U. Würz. 2003. Miscibility and phase behaviour of binary mixtures of N-palmitoylethanolamine and dipalmitoylphosphatidylcholine. Biochim. Biophys. Acta. 1616: 174-183.
    • (2003) Biochim. Biophys. Acta , vol.1616 , pp. 174-183
    • Swamy, M.J.1    Ramakrishnan, M.2    Marsh, D.3    Würz, U.4
  • 19
    • 0033983662 scopus 로고    scopus 로고
    • Derivatized lipids in membranes: Physico-chemical aspects of N-biotinyl phosphatidylethanolamines, N-acyl phosphatidylethanolamines and N-acylethanolamines
    • Marsh, D., and M. J. Swamy. 2000. Derivatized lipids in membranes: physico-chemical aspects of N-biotinyl phosphatidylethanolamines, N-acyl phosphatidylethanolamines and N-acylethanolamines. Chem. Phys. Lipids. 105: 43-69.
    • (2000) Chem. Phys. Lipids , vol.105 , pp. 43-69
    • Marsh, D.1    Swamy, M.J.2
  • 20
    • 33748991991 scopus 로고    scopus 로고
    • Endocannabinoid metabolism in the absence of fatty acid amide hydrolase (FAAH): Discovery of phosphorylcholine derivatives of N-acyl ethanolamines
    • Mulder, A. M., and B. F. Cravatt. 2006. Endocannabinoid metabolism in the absence of fatty acid amide hydrolase (FAAH): discovery of phosphorylcholine derivatives of N-acyl ethanolamines. Biochemistry. 45: 11267-11277.
    • (2006) Biochemistry , vol.45 , pp. 11267-11277
    • Mulder, A.M.1    Cravatt, B.F.2
  • 21
    • 34247882028 scopus 로고    scopus 로고
    • Synthesis of new plant growth regulator: N-(fatty acid) O-aryloxyacetyl ethanolamine
    • Han, L., J-R. Gao, Z-M. Li, Y. Zhang, and W-M. Guo. 2007. Synthesis of new plant growth regulator: N-(fatty acid) O-aryloxyacetyl ethanolamine. Bioorg. Med. Chem. Lett. 17: 3231-3234.
    • (2007) Bioorg. Med. Chem. Lett , vol.17 , pp. 3231-3234
    • Han, L.1    Gao, J.-R.2    Li, Z.-M.3    Zhang, Y.4    Guo, W.-M.5
  • 22
    • 0031568845 scopus 로고    scopus 로고
    • Preparation of N-, O-diacylethanolamine from N-acylethanolamine using lipase preparations
    • Furutani, T., H. Ooshima, and J. Kato. 1997. Preparation of N-, O-diacylethanolamine from N-acylethanolamine using lipase preparations. Enzyme Microb. Technol. 20: 214-220.
    • (1997) Enzyme Microb. Technol , vol.20 , pp. 214-220
    • Furutani, T.1    Ooshima, H.2    Kato, J.3
  • 24
    • 73149117545 scopus 로고    scopus 로고
    • Sheldrick, G. M. 1997. SHELXL97. Program for the refinement of crystal structures. University of Göttingen, Göttingen, Germany.
    • Sheldrick, G. M. 1997. SHELXL97. Program for the refinement of crystal structures. University of Göttingen, Göttingen, Germany.
  • 25
    • 0001752873 scopus 로고
    • Interchain vibrational coupling in phase II (hexagonal) n-alkanes
    • Casal, H. L., H. H. Mantsch, D. G. Cameron, and R. G. Snyder. 1982. Interchain vibrational coupling in phase II (hexagonal) n-alkanes. J. Chem. Phys. 77: 2825-2830.
    • (1982) J. Chem. Phys , vol.77 , pp. 2825-2830
    • Casal, H.L.1    Mantsch, H.H.2    Cameron, D.G.3    Snyder, R.G.4
  • 26
    • 0025013191 scopus 로고
    • Polymorphic behavior of 1,2-dipalmitoyl-3 -lauroyl(PPl2)-and 3-myristoyl(PP14)-sn-glycerols
    • Kodali, D. R., D. Atkinson, and D. M. Small. 1990. Polymorphic behavior of 1,2-dipalmitoyl-3 -lauroyl(PPl2)-and 3-myristoyl(PP14)-sn-glycerols. J. Lipid Res. 31: 1853-1864.
    • (1990) J. Lipid Res , vol.31 , pp. 1853-1864
    • Kodali, D.R.1    Atkinson, D.2    Small, D.M.3
  • 27
    • 33645781276 scopus 로고    scopus 로고
    • Structural study on polymorphism of pis-unsaturated triacylglycerol: Triolein
    • Akita, C., T. Kawaguchi, and F. Kaneko. 2006. Structural study on polymorphism of pis-unsaturated triacylglycerol: triolein. J. Phys. Chem. B. 110: 4346-4353.
    • (2006) J. Phys. Chem. B , vol.110 , pp. 4346-4353
    • Akita, C.1    Kawaguchi, T.2    Kaneko, F.3
  • 28
    • 0029594532 scopus 로고
    • Physical behavior of the hydrophobic core of membranes: Properties of 1-stearoyl-2-linoleoyl-sn-glycerol
    • Di, L., and D. M. Small. 1995. Physical behavior of the hydrophobic core of membranes: properties of 1-stearoyl-2-linoleoyl-sn-glycerol. Biochemistry. 34: 16672-16677.
    • (1995) Biochemistry , vol.34 , pp. 16672-16677
    • Di, L.1    Small, D.M.2
  • 29
    • 0001004821 scopus 로고
    • Physical properties-structural and physical characteristics
    • Handbook. F. D. Gunstone, J. L. Harwood, and F. B. Padley, editors. Chapman and Hall, London
    • Larsson, K. 1986. Physical properties-structural and physical characteristics. In The Lipid Handbook. F. D. Gunstone, J. L. Harwood, and F. B. Padley, editors. Chapman and Hall, London. 321-384.
    • (1986) The Lipid , pp. 321-384
    • Larsson, K.1
  • 30
    • 0031866573 scopus 로고    scopus 로고
    • Differential scanning calorimetric studies on the thermotropic phase transitions of N-acylethanolamines of odd chainlengths
    • Ramakrishnan, M., and M. J. Swamy. 1998. Differential scanning calorimetric studies on the thermotropic phase transitions of N-acylethanolamines of odd chainlengths. Chem. Phys. Lipids. 94: 43-51.
    • (1998) Chem. Phys. Lipids , vol.94 , pp. 43-51
    • Ramakrishnan, M.1    Swamy, M.J.2
  • 31
    • 0026079170 scopus 로고
    • Analysis of the chainlength dependence of lipid phase transition temperatures: Main and pretransitions of phosphatidylcholines; main and non-lamellar transitions of phosphatidylethanolamines
    • Marsh, D. 1991. Analysis of the chainlength dependence of lipid phase transition temperatures: main and pretransitions of phosphatidylcholines; main and non-lamellar transitions of phosphatidylethanolamines. Biochim. Biophys. Acta. 1062: 1-6.
    • (1991) Biochim. Biophys. Acta , vol.1062 , pp. 1-6
    • Marsh, D.1
  • 32
    • 0342429914 scopus 로고
    • Biomembranes
    • G. Pifat and J. N. Herak, editors. Plenum Press, New York
    • Marsh, D. 1982. Biomembranes. In Supramolecular Structure and Function. G. Pifat and J. N. Herak, editors. Plenum Press, New York. 127-178.
    • (1982) Supramolecular Structure and Function , pp. 127-178
    • Marsh, D.1
  • 33
    • 33746032601 scopus 로고    scopus 로고
    • Molecular packing and intermolecular interactioms in two structural polymorphs of N-palmitoylethanolamine, a type-2 cannabinoid receptor agonist
    • Kamlekar, R. K., and M. J. Swamy. 2006. Molecular packing and intermolecular interactioms in two structural polymorphs of N-palmitoylethanolamine, a type-2 cannabinoid receptor agonist. J. Lipid Res. 47: 1424-1433.
    • (2006) J. Lipid Res , vol.47 , pp. 1424-1433
    • Kamlekar, R.K.1    Swamy, M.J.2
  • 34
    • 0032896948 scopus 로고    scopus 로고
    • Molecular packing and intermolecular interactions in N-acylethanolamines: Crystal structure of N-myristoylethanolamine
    • Ramakrishnan, M., and M. J. Swamy. 1999. Molecular packing and intermolecular interactions in N-acylethanolamines: crystal structure of N-myristoylethanolamine. Biochim. Biophys. Acta. 1418: 261-267.
    • (1999) Biochim. Biophys. Acta , vol.1418 , pp. 261-267
    • Ramakrishnan, M.1    Swamy, M.J.2
  • 35
    • 0005135816 scopus 로고
    • The crystal structure of N-(2-hydroxyethyl)-octadecanoate
    • Dahlén, B., I. Pascher, and S. Sundell. 1977. The crystal structure of N-(2-hydroxyethyl)-octadecanoate. Acta Chem. Scand. A. 31: 313-320.
    • (1977) Acta Chem. Scand. A , vol.31 , pp. 313-320
    • Dahlén, B.1    Pascher, I.2    Sundell, S.3
  • 36
    • 0028784879 scopus 로고
    • Crystal structure of a mixed chain diacylglycerol, 1-stearoyl-3-oleyl-glycerol
    • Goto, M., K. Honda, L. Di, and D. M. Small. 1995. Crystal structure of a mixed chain diacylglycerol, 1-stearoyl-3-oleyl-glycerol. J. Lipid Res. 36: 2185-2190.
    • (1995) J. Lipid Res , vol.36 , pp. 2185-2190
    • Goto, M.1    Honda, K.2    Di, L.3    Small, D.M.4
  • 37
    • 0000571367 scopus 로고
    • Molecular arrangements in sphingolipids. Crystal structure of N-tetraeosanoylphytosphingosine
    • Dahlén, B., and I. Pascher. 1972. Molecular arrangements in sphingolipids. Crystal structure of N-tetraeosanoylphytosphingosine. Acta Crystallogr. B. 28: 2396-2404.
    • (1972) Acta Crystallogr. B , vol.28 , pp. 2396-2404
    • Dahlén, B.1    Pascher, I.2
  • 38
    • 0034629280 scopus 로고    scopus 로고
    • Physical properties of the transmembrane signal molecule, sn-1-stearoyl 2-arachidonoylglycerol. Acyl chain segregation and its biochemical implications
    • Hindenes, J-O., W. Nerdal, W. Guo, L. Di, D. M. Small, and H. Holmsen. 2000. Physical properties of the transmembrane signal molecule, sn-1-stearoyl 2-arachidonoylglycerol. Acyl chain segregation and its biochemical implications. J. Biol. Chem. 275: 6857-6867.
    • (2000) J. Biol. Chem , vol.275 , pp. 6857-6867
    • Hindenes, J.-O.1    Nerdal, W.2    Guo, W.3    Di, L.4    Small, D.M.5    Holmsen, H.6
  • 39
    • 0019882282 scopus 로고
    • Glycerol conformation and molecular packing of membrane lipids. The crystal structure of 2,3-dilauroyl-D-glycerol
    • Pascher, I., S. Sundell, and H. Hauser. 1981. Glycerol conformation and molecular packing of membrane lipids. The crystal structure of 2,3-dilauroyl-D-glycerol. J. Mol. Biol. 153: 791-806.
    • (1981) J. Mol. Biol , vol.153 , pp. 791-806
    • Pascher, I.1    Sundell, S.2    Hauser, H.3
  • 40
    • 0028364385 scopus 로고
    • The crystal structure of 1,2-dipalmitoyl-sn-glycerol at 123 K
    • Han, G. W., J. R. Ruble, and B. M. Craven. 1994. The crystal structure of 1,2-dipalmitoyl-sn-glycerol at 123 K. Chem. Phys. Lipids. 71: 219-228.
    • (1994) Chem. Phys. Lipids , vol.71 , pp. 219-228
    • Han, G.W.1    Ruble, J.R.2    Craven, B.M.3
  • 42
    • 0025652577 scopus 로고
    • Hydrocarbon chain packing modes in lipids: Effect of altered sub-cell dimensions and chain rotation
    • Maulik, P. R., M. J. Ruocco, and G. G. Shipley. 1990. Hydrocarbon chain packing modes in lipids: effect of altered sub-cell dimensions and chain rotation. Chem. Phys. Lipids. 56: 123-133.
    • (1990) Chem. Phys. Lipids , vol.56 , pp. 123-133
    • Maulik, P.R.1    Ruocco, M.J.2    Shipley, G.G.3
  • 43
  • 44
    • 0000216832 scopus 로고    scopus 로고
    • The C-HO hydrogen bond: Structural implications and supramolecular design
    • Desiraju, G. R. 1996. The C-HO hydrogen bond: structural implications and supramolecular design. Acc. Chem. Res. 29: 441-449.
    • (1996) Acc. Chem. Res , vol.29 , pp. 441-449
    • Desiraju, G.R.1
  • 45
    • 0037132626 scopus 로고    scopus 로고
    • Raman spectroscopic evidence for cooperative C - HO interactions in the acetaldehyde-CO complex
    • Blatchford, M. A., P. Raveendran, and S. L. Wallen. 2000. Raman spectroscopic evidence for cooperative C - HO interactions in the acetaldehyde-CO complex. J. Am. Chem. Soc. 124: 14818-14819.
    • (2000) J. Am. Chem. Soc , vol.124 , pp. 14818-14819
    • Blatchford, M.A.1    Raveendran, P.2    Wallen, S.L.3
  • 46
    • 7444249587 scopus 로고    scopus 로고
    • Evidence for hydrogen bond-like C-H-O interactions in aqueous 1,4-dioxane probed by high pressure
    • Chang, H-C., J-C. Jiang, C-W. Chuang, and S. H. Lin. 2004. Evidence for hydrogen bond-like C-H-O interactions in aqueous 1,4-dioxane probed by high pressure. Chem. Phys. Lett. 397: 205-210.
    • (2004) Chem. Phys. Lett , vol.397 , pp. 205-210
    • Chang, H.-C.1    Jiang, J.-C.2    Chuang, C.-W.3    Lin, S.H.4
  • 47
    • 0025605440 scopus 로고
    • Structure and polymorphism of saturated monoacid 1,2-diacyl-sn-glycerols
    • Kodali, D. R., D. A. Fahey, and D. M. Small. 1990. Structure and polymorphism of saturated monoacid 1,2-diacyl-sn-glycerols. Biochemistry. 29: 10771-10779.
    • (1990) Biochemistry , vol.29 , pp. 10771-10779
    • Kodali, D.R.1    Fahey, D.A.2    Small, D.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.