메뉴 건너뛰기




Volumn 17, Issue 21, 2010, Pages 2301-2324

Synthesis and structure-activity relationships of skin ceramides

Author keywords

Ceramides; Skin barrier; Sphingolipids; Sphingosine; Stratum corneum; Structure activity relationships; Synthesis

Indexed keywords

2 HYDROXYTETRACOSANOIC ACID; 30 (LINOLEYLOXY)TRIACONTANOIC ACID; 6 HYDROXYSPHINGOSINE; CERAMIDE; HYDROXY FATTY ACID; LINOLEIC ACID; OMEGA ACYLOXY FATTY ACID; PHYTOSPHINGOSINE; SPHINGANINE; SPHINGOSINE; UNCLASSIFIED DRUG; 6-HYDROXY-4-SPHINGENINE; SPHINGOLIPID;

EID: 77955617285     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/092986710791331068     Document Type: Article
Times cited : (29)

References (130)
  • 1
    • 33749049791 scopus 로고    scopus 로고
    • Epidermal sphingolipids: Metabolism, function, and roles in skin disorders
    • Holleran, W. M.; Takagi, Y.; Uchida, Y. Epidermal sphingolipids: metabolism, function, and roles in skin disorders. FEBS Lett, 2006, 580, 5456-66.
    • (2006) FEBS Lett. , vol.580 , pp. 5456-5466
    • Holleran, W.M.1    Takagi, Y.2    Uchida, Y.3
  • 2
    • 33845308573 scopus 로고    scopus 로고
    • The skin barrier in healthy and diseased state
    • Bouwstra, J. A.; Ponec, M. The skin barrier in healthy and diseased state. Biochim. Biophys. Acta, 2006, 1758, 2080-95.
    • (2006) Biochim. Biophys. Acta , vol.1758 , pp. 2080-2095
    • Bouwstra, J.A.1    Ponec, M.2
  • 3
    • 23844476054 scopus 로고    scopus 로고
    • Role of ceramides in barrier function of healthy and diseased skin
    • Choi, M. J.; Maibach, H. I. Role of ceramides in barrier function of healthy and diseased skin. Am. J. Clin. Dermatol., 2005, 6, 215-23.
    • (2005) Am. J. Clin. Dermatol. , vol.6 , pp. 215-223
    • Choi, M.J.1    Maibach, H.I.2
  • 4
    • 37249053783 scopus 로고    scopus 로고
    • Thematic review series: Skin lipids. The role of epidermal lipids in cutaneous permeability barrier homeostasis
    • Feingold, K. R. Thematic review series: skin lipids. The role of epidermal lipids in cutaneous permeability barrier homeostasis. J. Lipid Res., 2007, 48, 2531-46.
    • (2007) J. Lipid Res. , vol.48 , pp. 2531-2546
    • Feingold, K.R.1
  • 6
    • 77955623105 scopus 로고    scopus 로고
    • Skin Barrier CRC Press: NY
    • Elias, P. M.; Feingold, K. R. Skin Barrier CRC Press: NY 2006.
    • (2006)
    • Elias, P.M.1    Feingold, K.R.2
  • 7
    • 3543114272 scopus 로고    scopus 로고
    • Biologically active sphingolipids in cancer pathogenesis and treatment
    • Ogretmen, B.; Hannun, Y. A. Biologically active sphingolipids in cancer pathogenesis and treatment. Nat. Rev. Cancer, 2004, 4, 604-16.
    • (2004) Nat. Rev. Cancer , vol.4 , pp. 604-616
    • Ogretmen, B.1    Hannun, Y.A.2
  • 9
    • 34247642305 scopus 로고    scopus 로고
    • Pharmacological modulation of sphingolipids and role in disease and cancer cell biology
    • Morales, A.; Fernandez-Checa, J. C. Pharmacological modulation of sphingolipids and role in disease and cancer cell biology. Mini Rev. Med. Chem., 2007, 7, 371-82.
    • (2007) Mini Rev. Med. Chem. , vol.7 , pp. 371-382
    • Morales, A.1    Fernandez-Checa, J.C.2
  • 11
    • 0014824593 scopus 로고
    • Surface and bulk interactions of lipids and water with a classification of biologically active lipids based on these interactions
    • Small, D. M. Surface and bulk interactions of lipids and water with a classification of biologically active lipids based on these interactions. Fed. Proc., 1970, 29, 1320-6.
    • (1970) Fed. Proc. , vol.29 , pp. 1320-1326
    • Small, D.M.1
  • 12
    • 33845346790 scopus 로고    scopus 로고
    • Biophysics of sphingolipids I. Membrane properties of sphingosine, ceramides and other simple sphingolipids
    • Goni, F. M.; Alonso, A. Biophysics of sphingolipids I. Membrane properties of sphingosine, ceramides and other simple sphingolipids. Biochim. Biophys. Acta, 2006, 1758, 1902-21.
    • (2006) Biochim. Biophys. Acta , vol.1758 , pp. 1902-1921
    • Goni, F.M.1    Alonso, A.2
  • 16
    • 0032855937 scopus 로고    scopus 로고
    • Role of ceramides 2 and 5 in the structure of the stratum corneum lipid barrier
    • Moore, D. J.; Rerek, M. E.; Mendelsohn, R. Role of ceramides 2 and 5 in the structure of the stratum corneum lipid barrier. Int. J. Cosmet. Sci., 1999, 21, 353-68.
    • (1999) Int. J. Cosmet. Sci. , vol.21 , pp. 353-368
    • Moore, D.J.1    Rerek, M.E.2    Mendelsohn, R.3
  • 18
    • 0021085875 scopus 로고
    • Effect of essential fatty acid deficiency on the epidermal sphingolipids of the rat
    • Wertz, P. W.; Cho, E. S.; Downing, D. T. Effect of essential fatty acid deficiency on the epidermal sphingolipids of the rat. Biochim. Biophys. Acta., 1983, 753, 350-5.
    • (1983) Biochim. Biophys. Acta. , vol.753 , pp. 350-355
    • Wertz, P.W.1    Cho, E.S.2    Downing, D.T.3
  • 19
    • 6344275824 scopus 로고    scopus 로고
    • Acylceramide head group architecture affects lipid organization in synthetic ceramide mixtures
    • de Jager, M.; Gooris, G.; Ponec, M.; Bouwstra, J. Acylceramide head group architecture affects lipid organization in synthetic ceramide mixtures. J. Invest. Dermatol., 2004, 123, 911-6.
    • (2004) J. Invest. Dermatol. , vol.123 , pp. 911-916
    • de Jager, M.1    Gooris, G.2    Ponec, M.3    Bouwstra, J.4
  • 21
    • 0023068117 scopus 로고
    • Covalently bound omegahydroxyacylsphingosine in the stratum corneum
    • Wertz, P. W.; Downing, D. T. Covalently bound omegahydroxyacylsphingosine in the stratum corneum. Biochim. Biophys. Acta, 1987, 917, 108-11.
    • (1987) Biochim. Biophys. Acta , vol.917 , pp. 108-111
    • Wertz, P.W.1    Downing, D.T.2
  • 22
    • 0034954239 scopus 로고    scopus 로고
    • The omega-hydroxyceramides of pig epidermis are attached to corneocytes solely through omegahydroxyl groups
    • Stewart, M. E.; Downing, D. T. The omega-hydroxyceramides of pig epidermis are attached to corneocytes solely through omegahydroxyl groups. J. Lipid Res., 2001, 42, 1105-10.
    • (2001) J. Lipid Res. , vol.42 , pp. 1105-1110
    • Stewart, M.E.1    Downing, D.T.2
  • 23
    • 0031891166 scopus 로고    scopus 로고
    • The physical, chemical and functional properties of lipids in the skin and other biological barriers
    • Wertz, P. W.; van den Bergh, B. The physical, chemical and functional properties of lipids in the skin and other biological barriers. Chem. Phys. Lipids, 1998, 91, 85-96.
    • (1998) Chem. Phys. Lipids , vol.91 , pp. 85-96
    • Wertz, P.W.1    van den Bergh, B.2
  • 24
    • 0033988656 scopus 로고    scopus 로고
    • Lipid chain dynamics in stratum corneum studied by spin label electron paramagnetic resonance
    • Alonso, A.; Meirelles, N. C.; Tabak, M. Lipid chain dynamics in stratum corneum studied by spin label electron paramagnetic resonance. Chem. Phys. Lipids, 2000, 104, 101-11.
    • (2000) Chem. Phys. Lipids , vol.104 , pp. 101-111
    • Alonso, A.1    Meirelles, N.C.2    Tabak, M.3
  • 25
    • 45449109994 scopus 로고    scopus 로고
    • Omega-O-acylceramide, a lipid essential for mammalian survival
    • Uchida, Y.; Holleran, W. M. Omega-O-acylceramide, a lipid essential for mammalian survival. J. Dermatol. Sci., 2008, 51, 77-87.
    • (2008) J. Dermatol. Sci. , vol.51 , pp. 77-87
    • Uchida, Y.1    Holleran, W.M.2
  • 29
    • 28144431972 scopus 로고    scopus 로고
    • Acyl chain length affects ceramide action on sterol/sphingomyelin-rich domains
    • Nybond, S.; Bjorkqvist, Y. J.; Ramstedt, B.; Slotte, J. P. Acyl chain length affects ceramide action on sterol/sphingomyelin-rich domains. Biochim. Biophys. Acta, 2005, 1718, 61-6.
    • (2005) Biochim. Biophys. Acta , vol.1718 , pp. 61-66
    • Nybond, S.1    Bjorkqvist, Y.J.2    Ramstedt, B.3    Slotte, J.P.4
  • 30
    • 34548486456 scopus 로고    scopus 로고
    • Effect of ceramide N-acyl chain and polar headgroup structure on the properties of ordered lipid domains (lipid rafts)
    • Megha; Sawatzki, P.; Kolter, T.; Bittman, R.; London, E. Effect of ceramide N-acyl chain and polar headgroup structure on the properties of ordered lipid domains (lipid rafts). Biochim. Biophys. Acta., 2007, 1768, 2205-12.
    • (2007) Biochim. Biophys. Acta. , vol.1768 , pp. 2205-2212
    • Megha1    Sawatzki, P.2    Kolter, T.3    Bittman, R.4    London, E.5
  • 31
    • 34547181885 scopus 로고    scopus 로고
    • Raft domain reorganization driven by short- and long-chain ceramide: A combined AFM and FCS study
    • Chiantia, S.; Kahya, N.; Schwille, P. Raft domain reorganization driven by short- and long-chain ceramide: a combined AFM and FCS study. Langmuir, 2007, 23, 7659-65.
    • (2007) Langmuir , vol.23 , pp. 7659-7665
    • Chiantia, S.1    Kahya, N.2    Schwille, P.3
  • 32
    • 0041384271 scopus 로고    scopus 로고
    • Disruption of lipid order by short-chain ceramides correlates with inhibition of phospholipase D and downstream signaling by FcepsilonRI
    • Gidwani, A.; Brown, H. A.; Holowka, D.; Baird, B. Disruption of lipid order by short-chain ceramides correlates with inhibition of phospholipase D and downstream signaling by FcepsilonRI. J. Cell. Sci., 2003, 116, 3177-87.
    • (2003) J. Cell. Sci. , vol.116 , pp. 3177-3187
    • Gidwani, A.1    Brown, H.A.2    Holowka, D.3    Baird, B.4
  • 33
    • 23844512530 scopus 로고    scopus 로고
    • Amphiphilic transdermal permeation enhancers: Structure-activity relationships
    • Vavrova, K.; Zbytovska, J.; Hrabalek, A. Amphiphilic transdermal permeation enhancers: structure-activity relationships. Curr. Med. Chem., 2005, 12, 2273-91.
    • (2005) Curr. Med. Chem. , vol.12 , pp. 2273-2291
    • Vavrova, K.1    Zbytovska, J.2    Hrabalek, A.3
  • 35
    • 0027527545 scopus 로고
    • Selectivity of ceramide-mediated biology. Lack of activity of erythro-dihydroceramide
    • Bielawska, A.; Crane, H. M.; Liotta, D.; Obeid, L. M.; Hannun, Y. A. Selectivity of ceramide-mediated biology. Lack of activity of erythro-dihydroceramide. J. Biol. Chem., 1993, 268, 26226-32.
    • (1993) J. Biol. Chem. , vol.268 , pp. 26226-26232
    • Bielawska, A.1    Crane, H.M.2    Liotta, D.3    Obeid, L.M.4    Hannun, Y.A.5
  • 37
    • 0037375586 scopus 로고    scopus 로고
    • Designing anticancer drugs via the achilles heel: Ceramide, allylic ketones, and mitochondria
    • Radin, N. S. Designing anticancer drugs via the achilles heel: ceramide, allylic ketones, and mitochondria. Bioorg. Med. Chem., 2003, 11, 2123-42.
    • (2003) Bioorg. Med. Chem. , vol.11 , pp. 2123-2142
    • Radin, N.S.1
  • 38
    • 84938065936 scopus 로고    scopus 로고
    • Meta-analysis of anticancer drug structures-- significance of their polar allylic moieties
    • Radin, N. S. Meta-analysis of anticancer drug structures-- significance of their polar allylic moieties. Anticancer Agents Med. Chem., 2007, 7, 209-22.
    • (2007) Anticancer Agents Med. Chem. , vol.7 , pp. 209-222
    • Radin, N.S.1
  • 39
    • 34548564146 scopus 로고    scopus 로고
    • Ceramide analogue 14S24 selectively recovers perturbed human skin barrier
    • Vavrova, K.; Hrabalek, A.; Mac-Mary, S.; Humbert, P.; Muret, P. Ceramide analogue 14S24 selectively recovers perturbed human skin barrier. Br. J. Dermatol., 2007, 157, 704-12.
    • (2007) Br. J. Dermatol. , vol.157 , pp. 704-712
    • Vavrova, K.1    Hrabalek, A.2    Mac-Mary, S.3    Humbert, P.4    Muret, P.5
  • 40
    • 18344419439 scopus 로고    scopus 로고
    • Ceramide analogue 14S24 ((S)-2- tetracosanoylamino-3-hydroxypropionic acid tetradecyl ester) is effective in skin barrier repair in vitro
    • Vavrova, K.; Zbytovska, J.; Palat, K.; Holas, T.; Klimentova, J.; Hrabalek, A.; Dolezal, P.Ceramide analogue 14S24 ((S)-2- tetracosanoylamino-3-hydroxypropionic acid tetradecyl ester) is effective in skin barrier repair in vitro. Eur. J. Pharm. Sci., 2004, 21, 581-7.
    • (2004) Eur. J. Pharm. Sci. , vol.21 , pp. 581-587
    • Vavrova, K.1    Zbytovska, J.2    Palat, K.3    Holas, T.4    Klimentova, J.5    Hrabalek, A.6    Dolezal, P.7
  • 41
    • 4444348709 scopus 로고    scopus 로고
    • The 4,5-double bond of ceramide regulates its dipole potential, elastic properties, and packing behavior
    • Brockman, H. L.; Momsen, M. M.; Brown, R. E.; He, L.; Chun, J.; Byun, H. S.; Bittman, R. The 4,5-double bond of ceramide regulates its dipole potential, elastic properties, and packing behavior. Biophys. J., 2004, 87, 1722-31.
    • (2004) Biophys. J. , vol.87 , pp. 1722-1731
    • Brockman, H.L.1    Momsen, M.M.2    Brown, R.E.3    He, L.4    Chun, J.5    Byun, H.S.6    Bittman, R.7
  • 42
    • 0036214899 scopus 로고    scopus 로고
    • Conformational characterization of ceramides by nuclear magnetic resonance spectroscopy
    • Li, L.; Tang, X.; Taylor, K. G.; DuPre, D. B.; Yappert, M. C. Conformational characterization of ceramides by nuclear magnetic resonance spectroscopy. Biophys. J., 2002, 82, 2067-80.
    • (2002) Biophys. J. , vol.82 , pp. 2067-2080
    • Li, L.1    Tang, X.2    Taylor, K.G.3    Dupre, D.B.4    Yappert, M.C.5
  • 43
    • 57749091301 scopus 로고    scopus 로고
    • Dicarboxylic acid esters as transdermal permeation enhancers: Effects of chain number and geometric isomers
    • Novotny, M.; Hrabalek, A.; Janusova, B.; Novotny, J.; Vavrova, K. Dicarboxylic acid esters as transdermal permeation enhancers: effects of chain number and geometric isomers. Bioorg. Med. Chem. Lett., 2009, 19, 344-7.
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 344-347
    • Novotny, M.1    Hrabalek, A.2    Janusova, B.3    Novotny, J.4    Vavrova, K.5
  • 44
    • 0035960199 scopus 로고    scopus 로고
    • Phytosphingosine and Sphingosine Ceramide Headgroup Hydrogen Bonding: Structural Insights through Thermotropic Hydrogen/Deuterium Exchange
    • Rerek, M. E.; Chen; Markovic, B.; Van Wyck, D.; Garidel, P.; Mendelsohn, R.; Moore, D. J. Phytosphingosine and Sphingosine Ceramide Headgroup Hydrogen Bonding: Structural Insights through Thermotropic Hydrogen/Deuterium Exchange. J. Phys. Chem. B, 2001, 105, 9355-9362.
    • (2001) J. Phys. Chem. B , vol.105 , pp. 9355-9362
    • Rerek, M.E.1
  • 45
    • 0017636970 scopus 로고
    • Molecular arrangements of sphingolipids. The monolayer behaviour of ceramides
    • Lofgren, H.; Pascher, I. Molecular arrangements of sphingolipids. The monolayer behaviour of ceramides. Chem. Phys. Lipids, 1977, 20, 273-84.
    • (1977) Chem. Phys. Lipids , vol.20 , pp. 273-284
    • Lofgren, H.1    Pascher, I.2
  • 46
    • 0027955474 scopus 로고
    • A domain mosaic model of the skin barrier
    • Forslind, B. A domain mosaic model of the skin barrier. Acta. Derm. Venereol., 1994, 74, 1-6.
    • (1994) Acta. Derm Venereol. , vol.74 , pp. 1-6
    • Forslind, B.1
  • 47
    • 0033656472 scopus 로고    scopus 로고
    • Insights into the molecular organization of lipids in the skin barrier from infrared spectroscopy studies of stratum corneum lipid models
    • Moore, D. J.; Rerek, M. E. Insights into the molecular organization of lipids in the skin barrier from infrared spectroscopy studies of stratum corneum lipid models. Acta. Derm. Venereol. Suppl. (Stockh), 2000, 208, 16-22.
    • (2000) Acta. Derm. Venereol. Suppl. (Stockh) , vol.208 , pp. 16-22
    • Moore, D.J.1    Rerek, M.E.2
  • 48
    • 0036254009 scopus 로고    scopus 로고
    • Calorimetric and spectroscopic investigations of phytosphingosine ceramide membrane organisation
    • Garidel, P. Calorimetric and spectroscopic investigations of phytosphingosine ceramide membrane organisation. Phys. Chem. Chem. Phys., 2002, 4, 1934-42.
    • (2002) Phys. Chem. Chem. Phys. , vol.4 , pp. 1934-1942
    • Garidel, P.1
  • 50
    • 0031873509 scopus 로고    scopus 로고
    • Sphingosine, an Enigmatic Lipid: A Review of Recent Literature Syntheses
    • Koskinen, P. i. M.; Koskinen, A. M. P. Sphingosine, an Enigmatic Lipid: A Review of Recent Literature Syntheses. Synthesis, 1998, 1998, 1075-1091.
    • (1998) Synthesis , vol.1998 , pp. 1075-1091
    • Koskinen, P.I.M.1    Koskinen, A.M.P.2
  • 51
    • 0001211029 scopus 로고
    • Zur Chemie des Fliegenpilzes (Amanita muscaria L.)
    • Zellner, J. Zur Chemie des Fliegenpilzes (Amanita muscaria L.). Monatshefte für Chemie/Chemical Monthly, 1911, 32, 133-142.
    • (1911) Monatshefte Für Chemie/Chemical Monthly , vol.32 , pp. 133-142
    • Zellner, J.1
  • 53
    • 27844464047 scopus 로고    scopus 로고
    • Synthesis and absolute configuration of 6- hydroxylated new ceramides in human skin, ceramides B, 4, 7 and 8
    • Masuda, Y.; Mori, K. Synthesis and absolute configuration of 6- hydroxylated new ceramides in human skin, ceramides B, 4, 7 and 8. Eur. J. Org. Chem., 2005, 2005, 4789-4800.
    • (2005) Eur. J. Org. Chem. , vol.2005 , pp. 4789-4800
    • Masuda, Y.1    Mori, K.2
  • 54
    • 0016054815 scopus 로고
    • Resolution and chromatographic configuration analysis of 2-hydroxy fatty acids
    • Karlsson, K. A.; Pascher, I. Resolution and chromatographic configuration analysis of 2-hydroxy fatty acids. Chem. Phys. Lipids, 1974, 12, 65-74.
    • (1974) Chem. Phys. Lipids , vol.12 , pp. 65-74
    • Karlsson, K.A.1    Pascher, I.2
  • 55
    • 0028843878 scopus 로고
    • Does solute stereochemistry influence percutaneous penetration?
    • Heard, C. M.; Brain, K. R. Does solute stereochemistry influence percutaneous penetration? Chirality, 1995, 7, 305-9.
    • (1995) Chirality , vol.7 , pp. 305-309
    • Heard, C.M.1    Brain, K.R.2
  • 57
    • 0036430094 scopus 로고    scopus 로고
    • Enhancement effects of (R) and (S) enantiomers and the racemate of a model enhancer on permeation of theophylline through human skin
    • Vavrova, K.; Hrabalek, A.; Dolezal, P. Enhancement effects of (R) and (S) enantiomers and the racemate of a model enhancer on permeation of theophylline through human skin. Arch. Dermatol. Res., 2002, 294, 383-5.
    • (2002) Arch. Dermatol. Res. , vol.294 , pp. 383-385
    • Vavrova, K.1    Hrabalek, A.2    Dolezal, P.3
  • 58
    • 61449262804 scopus 로고    scopus 로고
    • Dimethylamino acid esters as biodegradable and reversible transdermal permeation enhancers: Effects of linking chain length, chirality and polyfluorination
    • Novotny, J.; Kovarikova, P.; Novotny, M.; Janusova, B.; Hrabalek, A.; Vavrova, K. Dimethylamino acid esters as biodegradable and reversible transdermal permeation enhancers: effects of linking chain length, chirality and polyfluorination. Pharm. Res., 2009, 26, 811-21.
    • (2009) Pharm. Res. , vol.26 , pp. 811-821
    • Novotny, J.1    Kovarikova, P.2    Novotny, M.3    Janusova, B.4    Hrabalek, A.5    Vavrova, K.6
  • 59
    • 0034778702 scopus 로고    scopus 로고
    • Skin barrier structure and function: The single gel phase model
    • Norlen, L. Skin barrier structure and function: the single gel phase model. J. Invest. Dermatol., 2001, 117, 830-6.
    • (2001) J. Invest. Dermatol. , vol.117 , pp. 830-836
    • Norlen, L.1
  • 60
    • 0001510409 scopus 로고    scopus 로고
    • On the swelling of amphiphiles in water
    • Corkery, R. W.; Hyde, S. T. On the Swelling of Amphiphiles in Water. Langmuir, 1996, 12, 5528-5529.
    • (1996) Langmuir , vol.12 , pp. 5528-5529
    • Corkery, R.W.1    Hyde, S.T.2
  • 62
    • 0036070734 scopus 로고    scopus 로고
    • The anti-parallel, extended or splayed-chain conformation of amphiphilic lipids
    • Corkery, R. W. The anti-parallel, extended or splayed-chain conformation of amphiphilic lipids. Colloid. Surf. B: Biointerfaces, 2002, 26, 3-20.
    • (2002) Colloid. Surf. B: Biointerfaces , vol.26 , pp. 3-20
    • Corkery, R.W.1
  • 63
    • 0344631776 scopus 로고    scopus 로고
    • Biophysics of ceramide signaling: Interaction with proteins and phase transition of membranes
    • Kronke, M. Biophysics of ceramide signaling: interaction with proteins and phase transition of membranes. Chem. Phys. Lipids, 1999, 101, 109-21.
    • (1999) Chem. Phys. Lipids , vol.101 , pp. 109-121
    • Kronke, M.1
  • 64
    • 0040892134 scopus 로고
    • Chemische Totalsynthese von Sphingosin, dem zentralen Baustein der Sphingolipide
    • Devant, R. M. Chemische Totalsynthese von Sphingosin, dem zentralen Baustein der Sphingolipide. Kontakte, 1992, 3, 11-28.
    • (1992) Kontakte , vol.3 , pp. 11-28
    • Devant, R.M.1
  • 65
    • 0036231270 scopus 로고    scopus 로고
    • The Preparation and Biological Significance of Phytosphingosines
    • Howell, A. R.; Ndakala, A. J. The Preparation and Biological Significance of Phytosphingosines. Curr. Org. Chem., 2002, 6, 365-391.
    • (2002) Curr. Org. Chem. , vol.6 , pp. 365-391
    • Howell, A.R.1    Ndakala, A.J.2
  • 66
    • 8744278061 scopus 로고    scopus 로고
    • Approaches to the preparation of sphinganines
    • Howell, A. R.; So, R. C.; Richardson, S. K. Approaches to the preparation of sphinganines. Tetrahedron, 2004, 60, 11327-11347.
    • (2004) Tetrahedron , vol.60 , pp. 11327-11347
    • Howell, A.R.1    So, R.C.2    Richardson, S.K.3
  • 67
    • 0005009475 scopus 로고
    • The synthesis of sphingosine
    • Shapiro, D.; Segal, K. The synthesis of sphingosine. J. Am. Chem. Soc., 1954, 76, 5894-95.
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 5894-5895
    • Shapiro, D.1    Segal, K.2
  • 68
    • 0347756774 scopus 로고
    • Synthesis of d-erythrosphingosines
    • Schmidt, R. R.; Zimmermann, P. Synthesis of d-erythrosphingosines. Tetrahedron Lett., 1986, 27, 481-484.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 481-484
    • Schmidt, R.R.1    Zimmermann, P.2
  • 69
    • 0022642264 scopus 로고
    • A Convenient synthesis of sphingosine and ceramide from Dxylose or D-galactose
    • Kiso, M.; Nakamura, A.; Nakamura, J.; Tomita, Y.; Hasegawa, A. A Convenient synthesis of sphingosine and ceramide from Dxylose or D-galactose. J. Carbohydr. Chem., 1986, 5, 335-340.
    • (1986) J. Carbohydr. Chem. , vol.5 , pp. 335-340
    • Kiso, M.1    Nakamura, A.2    Nakamura, J.3    Tomita, Y.4    Hasegawa, A.5
  • 70
    • 0000732955 scopus 로고
    • Enantioselective Synthesis of D-erythro-Sphingosine and of Ceramide
    • Julina, R.; Herzig, T.; Bernet, B.; Vasella, A. Enantioselective Synthesis of D-erythro-Sphingosine and of Ceramide. Helv. Chim. Acta, 1986, 69, 368-373.
    • (1986) Helv. Chim. Acta , vol.69 , pp. 368-373
    • Julina, R.1    Herzig, T.2    Bernet, B.3    Vasella, A.4
  • 71
    • 0023684709 scopus 로고
    • A stereodivergent synthesis of D-erythro-sphingosine and D-threo-sphingosine from L-serine
    • Garner, P.; Park, J. M.; Malecki, E. A stereodivergent synthesis of D-erythro-sphingosine and D-threo-sphingosine from L-serine. J. Org. Chem., 1988, 53, 4395-4398.
    • (1988) J. Org. Chem. , vol.53 , pp. 4395-4398
    • Garner, P.1    Park, J.M.2    Malecki, E.3
  • 72
    • 0023838180 scopus 로고
    • Synthesis of D-Erythro- and D-Threo-Sphingosine derivatives from L-Serine
    • Herold, P. Synthesis of D-Erythro- and D-Threo-Sphingosine Derivatives From L-Serine. Helv. Chim. Acta, 1988, 71, 354-362.
    • (1988) Helv. Chim. Acta , vol.71 , pp. 354-362
    • Herold, P.1
  • 73
    • 0000688013 scopus 로고
    • 1,1,-Dimethylethyl (S)- or (R)-4-Formyl- 2,2-Dimethyl-3-Ooxazolidinecarboxylate: A Useful Serinal Derivative
    • Garner, P.; Park, J. M. 1,1,-Dimethylethyl (S)- or (R)-4-Formyl- 2,2-Dimethyl-3-Ooxazolidinecarboxylate: A Useful Serinal Derivative. Org. Synth., 1992, 9, 300.
    • (1992) Org. Synth. , vol.9 , pp. 300
    • Garner, P.1    Park, J.M.2
  • 74
    • 0032572894 scopus 로고    scopus 로고
    • Use of heterocycles as chiral ligands and auxiliaries in asymmetric syntheses of sphingosine, sphingofungins B and F
    • Kobayashi, S.; Furuta, T. Use of heterocycles as chiral ligands and auxiliaries in asymmetric syntheses of sphingosine, sphingofungins B and F. Tetrahedron, 1998, 54, 10275-10294.
    • (1998) Tetrahedron , vol.54 , pp. 10275-10294
    • Kobayashi, S.1    Furuta, T.2
  • 75
    • 0000174699 scopus 로고    scopus 로고
    • Synthesis of d-erythro- and l-threo- Sphingosine and Sphinganine Diastereomers via the Biomimetic Precursor 3-Ketosphinganine
    • Hoffman, R. V.; Tao, J. A Synthesis of d-erythro- and l-threo- Sphingosine and Sphinganine Diastereomers via the Biomimetic Precursor 3-Ketosphinganine. J. Org. Chem., 1998, 63, 3979-3985.
    • (1998) J. Org. Chem. , vol.63 , pp. 3979-3985
    • Hoffman, R.V.1    Tao, J.A.2
  • 76
    • 0023926243 scopus 로고
    • Synthetic studies of didemnins. III: Syntheses of statine and isostatine stereoisomers
    • Harris, B. D.; Joullié, M. M. Synthetic studies of didemnins. III: Syntheses of statine and isostatine stereoisomers. Tetrahedron, 1988, 44, 3489-3500.
    • (1988) Tetrahedron , vol.44 , pp. 3489-3500
    • Harris, B.D.1    Joullié, M.M.2
  • 77
    • 0001638532 scopus 로고    scopus 로고
    • An Improved Enantiospecific Synthesis of Statine and Statine Analogs via 4-(N,N-Dibenzylamino)-3-keto Esters
    • Hoffman, R. V.; Tao, J. An Improved Enantiospecific Synthesis of Statine and Statine Analogs via 4-(N,N-Dibenzylamino)-3-keto Esters. J. Org. Chem., 1997, 62, 2292-2297.
    • (1997) J. Org. Chem. , vol.62 , pp. 2292-2297
    • Hoffman, R.V.1    Tao, J.2
  • 78
    • 0033618299 scopus 로고    scopus 로고
    • A short enantiodivergent synthesis of d-erythro and l-threo sphingosine
    • Khiar, N.; Singh, K.; García, M.; Martín-Lomas, M. A short enantiodivergent synthesis of d-erythro and l-threo sphingosine. Tetrahedron Lett., 1999, 40, 5779-5782.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5779-5782
    • Khiar, N.1    Singh, K.2    García, M.3    Martín-Lomas, M.4
  • 79
    • 84987584314 scopus 로고
    • Improved Preparation of Optically Active Methyl p-Tolyl Sulfoxide
    • Solladie, G.; Hutt, J.; Girardin, A. Improved Preparation of Optically Active Methyl p-Tolyl Sulfoxide. Synthesis, 1987, 1987, 173-173.
    • (1987) Synthesis , vol.1987 , pp. 173-173
    • Solladie, G.1    Hutt, J.2    Girardin, A.3
  • 80
    • 0033546109 scopus 로고    scopus 로고
    • Asymmetric alpha-chloroallylboration of amino aldehydes: A novel and highly versatile route to d- and lerythro- sphingoid bases
    • Hertweck, C.; Boland, W. Asymmetric alpha-chloroallylboration of amino aldehydes: A novel and highly versatile route to d- and lerythro- sphingoid bases. J. Org. Chem., 1999, 64, 4426-4430.
    • (1999) J. Org. Chem. , vol.64 , pp. 4426-4430
    • Hertweck, C.1    Boland, W.2
  • 81
    • 0034723252 scopus 로고    scopus 로고
    • A chemoenzymatic access to D - and L -Sphingosines employing hydroxynitrile lyases
    • Johnson, D. V.; Felfer, U.; Griengl, H. A chemoenzymatic access to D - and L -Sphingosines employing hydroxynitrile lyases. Tetrahedron, 2000, 56, 781-790.
    • (2000) Tetrahedron , vol.56 , pp. 781-790
    • Johnson, D.V.1    Felfer, U.2    Griengl, H.3
  • 82
    • 0034602328 scopus 로고    scopus 로고
    • Stereoselective preparation of ceramide and its skeleton backbone modified analogues via cyclic thionocarbonate intermediates derived by catalytic asymmetric dihydroxylation of,-unsaturated ester
    • He, L.; Byun, H.-S.; Bittman, R. Stereoselective preparation of ceramide and its skeleton backbone modified analogues via cyclic thionocarbonate intermediates derived by catalytic asymmetric dihydroxylation of,-unsaturated ester J. Org. Chem., 2000, 65, 7627-7633.
    • (2000) J. Org. Chem. , vol.65 , pp. 7627-7633
    • He, L.1    Byun, H.-S.2    Bittman, R.3
  • 83
    • 0025127095 scopus 로고
    • Total syntheses of penicillanic acid S,S-dioxide and 6-aminopenicillanic acid using (benzyloxy) nitromethane
    • Barrett, A. G. M.; Sakadarat, S. Total syntheses of penicillanic acid S,S-dioxide and 6-aminopenicillanic acid using (benzyloxy) nitromethane. J. Org. Chem., 1990, 55, 5110-5117.
    • (1990) J. Org. Chem. , vol.55 , pp. 5110-5117
    • Barrett, A.G.M.1    Sakadarat, S.2
  • 84
    • 0035968851 scopus 로고    scopus 로고
    • Stereoselective synthesis of D-erythrosphingosine and L-lyxo-phytosphingosine
    • Nakamura, T.; Shiozaki, M. Stereoselective synthesis of D-erythrosphingosine and L-lyxo-phytosphingosine. Tetrahedron, 2001, 57, 9087-9092.
    • (2001) Tetrahedron , vol.57 , pp. 9087-9092
    • Nakamura, T.1    Shiozaki, M.2
  • 85
    • 0034926817 scopus 로고    scopus 로고
    • The total syntheses of D-erythro-sphingosine, Npalmitoylsphingosine (ceramide), and glucosylceramide (cerebroside) via an azidosphingosine analog
    • Duclos, R. I. The total syntheses of D-erythro-sphingosine, Npalmitoylsphingosine (ceramide), and glucosylceramide (cerebroside) via an azidosphingosine analog. Chem. Phys. Lipids, 2001, 111, 111-38.
    • (2001) Chem. Phys. Lipids , vol.111 , pp. 111-138
    • Duclos, R.I.1
  • 87
    • 0037155732 scopus 로고    scopus 로고
    • A short and efficient stereoselective synthesis of all four diastereomers of sphingosine
    • Lee, J.-M.; Lim, H.-S.; Chung, S.-K. A short and efficient stereoselective synthesis of all four diastereomers of sphingosine. Tetrahedron Asymmetry, 2002, 13, 343-347.
    • (2002) Tetrahedron Asymmetry , vol.13 , pp. 343-347
    • Lee, J.-M.1    Lim, H.-S.2    Chung, S.-K.3
  • 88
    • 0037145169 scopus 로고    scopus 로고
    • A Stereocontrolled Synthesis of D-erythro-Sphingosine and D-ribo-Phytosphingsine
    • Kang, S. H.; Hwang, Y. S.; Lee, H. S. A Stereocontrolled Synthesis of D-erythro-Sphingosine and D-ribo-Phytosphingsine. Bull. Korean Chem. Soc., 2002, 23, 1195-1196.
    • (2002) Bull. Korean Chem. Soc. , vol.23 , pp. 1195-1196
    • Kang, S.H.1    Hwang, Y.S.2    Lee, H.S.3
  • 89
    • 0037459676 scopus 로고    scopus 로고
    • Divergent Synthesis of D-erythro- Sphingosine, L-threo-Sphingosine, and Their Regioisomers
    • Olofsson, B.; Somfai, P. Divergent Synthesis of D-erythro- Sphingosine, L-threo-Sphingosine, and Their Regioisomers. J. Org. Chem., 2003, 68, 2514-2517.
    • (2003) J. Org. Chem. , vol.68 , pp. 2514-2517
    • Olofsson, B.1    Somfai, P.2
  • 90
    • 0037074113 scopus 로고    scopus 로고
    • A concise route to derythro- sphingosine from N-Boc-l-serine derivatives via sulfoxide or sulfone intermediates
    • Chun, J.; Li, G.; Byun, H.-S.; Bittman, R. A concise route to derythro- sphingosine from N-Boc-l-serine derivatives via sulfoxide or sulfone intermediates. Tetrahedron Lett., 2002, 43, 375-377.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 375-377
    • Chun, J.1    Li, G.2    Byun, H.-S.3    Bittman, R.4
  • 91
    • 0037064401 scopus 로고    scopus 로고
    • A simple and low cost synthesis of d-erythro-sphingosine and d-erythro-azidosphingosine from d-ribo-phytosphingosine: Glycosphingolipid precursors
    • van den Berg, R. J. B. H. N.; Korevaar, C. G. N.; van der Marel, G. A.; Overkleeft, H. S.; van Boom, J. H. A simple and low cost synthesis of d-erythro-sphingosine and d-erythro-azidosphingosine from d-ribo-phytosphingosine: glycosphingolipid precursors. Tetrahedron Lett., 2002, 43, 8409-8412.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 8409-8412
    • van den Berg, R.J.B.H.N.1    Korevaar, C.G.N.2    van der Marel, G.A.3    Overkleeft, H.S.4    van Boom, J.H.5
  • 92
    • 0028073668 scopus 로고
    • Sphingosine and phytosphingosine from D-threose synthesis of a 4-keto-ceramide
    • Wild, R.; Schmidt, R. R. Sphingosine and phytosphingosine from D-threose synthesis of a 4-keto-ceramide. Tetrahedron Asymmetry, 1994, 5, 2195-2208.
    • (1994) Tetrahedron Asymmetry , vol.5 , pp. 2195-2208
    • Wild, R.1    Schmidt, R.R.2
  • 93
    • 4043175402 scopus 로고    scopus 로고
    • Effective, high-yielding, and stereospecific total synthesis of D-erythro-(2R,3S)-sphingosine from Dribo-(2S,3S,4R)-phytosphingosine
    • van den Berg, R. J.; Korevaar, C. G.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. Effective, high-yielding, and stereospecific total synthesis of D-erythro-(2R,3S)-sphingosine from Dribo-(2S,3S,4R)-phytosphingosine. J. Org. Chem., 2004, 69, 5699-704.
    • (2004) J. Org. Chem. , vol.69 , pp. 5699-5704
    • van den Berg, R.J.1    Korevaar, C.G.2    Overkleeft, H.S.3    van der Marel, G.A.4    van Boom, J.H.5
  • 94
    • 0026495369 scopus 로고
    • A simplified procedure for the stereospecific transformation of 1,2-diols into epoxides
    • Kolb, H. C.; Sharpless, K. B. A simplified procedure for the stereospecific transformation of 1,2-diols into epoxides. Tetrahedron, 1992, 48, 10515-10530.
    • (1992) Tetrahedron , vol.48 , pp. 10515-10530
    • Kolb, H.C.1    Sharpless, K.B.2
  • 95
    • 0002443721 scopus 로고
    • Phase Transfer-Catalyzed preparation of oxiranes
    • Szeja, W. Phase Transfer-Catalyzed preparation of oxiranes. Synthesis, 1985, 983-985.
    • (1985) Synthesis , pp. 983-985
    • Szeja, W.1
  • 96
    • 0041837315 scopus 로고    scopus 로고
    • Novel, short, stereospecific synthesis of lyxo-(2R,3R,4R)-phytosphingosine and erythro-(2R,3S)- sphingosine
    • Raghavan, S.; Rajender, A. Novel, short, stereospecific synthesis of lyxo-(2R,3R,4R)-phytosphingosine and erythro-(2R,3S)- sphingosine. J. Org. Chem., 2003, 68, 7094-7.
    • (2003) J. Org. Chem. , vol.68 , pp. 7094-7097
    • Raghavan, S.1    Rajender, A.2
  • 97
    • 2942752245 scopus 로고    scopus 로고
    • A practical synthesis of D-erythrosphingosine using a cross-metathesis approach
    • Torssell, S.; Somfai, P. A practical synthesis of D-erythrosphingosine using a cross-metathesis approach. Org. Biomol. Chem., 2004, 2, 1643-1646.
    • (2004) Org. Biomol. Chem. , vol.2 , pp. 1643-1646
    • Torssell, S.1    Somfai, P.2
  • 98
    • 0034549491 scopus 로고    scopus 로고
    • Chemo-Enzymatic total synthesis of 3- Epiaustraline, Australine, and 7-Epialexine
    • Romero, A.; Wong, C.-H.Chemo-Enzymatic total synthesis of 3- Epiaustraline, Australine, and 7-Epialexine. J. Org. Chem., 2000, 65, 8264-8268.
    • (2000) J. Org. Chem. , vol.65 , pp. 8264-8268
    • Romero, A.1    Wong, C.-H.2
  • 99
    • 25444470542 scopus 로고    scopus 로고
    • Synthesis of the glycosphingolipid β- galactosyl ceramide and analogues via olefin cross metathesis
    • Rai, A. N.; Basu, A. Synthesis of the glycosphingolipid β- galactosyl ceramide and analogues via olefin cross metathesis. J. Org. Chem., 2005, 70, 8228-8230.
    • (2005) J. Org. Chem. , vol.70 , pp. 8228-8230
    • Rai, A.N.1    Basu, A.2
  • 100
    • 4444382295 scopus 로고    scopus 로고
    • Sphingolipid synthesis via olefin cross metathesis: Preparation of a differentially protected building block and application to the synthesis of D-erythro-ceramide
    • Rai, A. N.; Basu, A. Sphingolipid synthesis via olefin cross metathesis: preparation of a differentially protected building block and application to the synthesis of D-erythro-ceramide. Org. Lett., 2004, 6, 2861-2863.
    • (2004) Org. Lett. , vol.6 , pp. 2861-2863
    • Rai, A.N.1    Basu, A.2
  • 101
    • 77955592671 scopus 로고    scopus 로고
    • WO/2003/101937
    • Bundle, D.; Ling, C. C., 2003; Vol. WO/2003/101937.
    • (2003)
    • Bundle, D.1    Ling, C.C.2
  • 102
    • 13944283368 scopus 로고    scopus 로고
    • Efficient and versatile synthesis of (2S,3R)- sphingosine and its 2-azido-3-O-benzylsphingosine analogue
    • Lu, X.; Bittman, R.Efficient and versatile synthesis of (2S,3R)- sphingosine and its 2-azido-3-O-benzylsphingosine analogue. Tetrahedron Lett., 2005, 46, 1873-1875.
    • (2005) Tetrahedron Lett. , vol.46 , pp. 1873-1875
    • Lu, X.1    Bittman, R.2
  • 103
    • 27744483875 scopus 로고    scopus 로고
    • Chirality transfer from guanidinium ylides to 3-alkenyl (or 3-alkynyl) aziridine-2-carboxylates and application to the syntheses of (2R,3S)-3-hydroxyleucinate and Derythro- sphingosine
    • Disadee, W.; Ishikawa, T. Chirality transfer from guanidinium ylides to 3-alkenyl (or 3-alkynyl) aziridine-2-carboxylates and application to the syntheses of (2R,3S)-3-hydroxyleucinate and Derythro- sphingosine. J. Org. Chem., 2005, 70, 9399-406.
    • (2005) J. Org. Chem. , vol.70 , pp. 9399-9406
    • Disadee, W.1    Ishikawa, T.2
  • 104
    • 30144438606 scopus 로고    scopus 로고
    • An Efficient Synthesis of D-erythro- and D-threo-Sphingosine from D-Glucose: Olefin Cross-Metathesis Approach
    • Chaudhari, V. D.; Kumar, K. S. A.; Dhavale, D. D. An Efficient Synthesis of D-erythro- and D-threo-Sphingosine from D-Glucose: Olefin Cross-Metathesis approach. Org. Lett., 2005, 7, 5805-5807.
    • (2005) Org. Lett. , vol.7 , pp. 5805-5807
    • Chaudhari, V.D.1    Kumar, K.S.A.2    Dhavale, D.D.3
  • 105
    • 0035891742 scopus 로고    scopus 로고
    • Sugar amino acid containing somatostatin analogues that induce apoptosis in both drug-sensitive and multidrug-resistant tumor cells
    • Gruner, S. A. W.; Kéri, G.; Schwab, R.; Venetianer, A.; Kessler, H. Sugar amino acid containing somatostatin analogues that induce apoptosis in both drug-sensitive and multidrug-resistant tumor cells. Org. Lett., 2001, 6, 3723-3725.
    • (2001) Org. Lett. , vol.6 , pp. 3723-3725
    • Gruner, S.A.W.1    Kéri, G.2    Schwab, R.3    Venetianer, A.4    Kessler, H.5
  • 106
    • 33744932158 scopus 로고    scopus 로고
    • Enantiodivergent Synthesis of D- and L-erythro-Sphingosines through Mannich-Type Reactions of N-Benzyl-2,3-O-isopropylidene-D-glyceraldehyde Nitrone
    • Merino, P.; Jimenez, P.; Tejero, T. Enantiodivergent Synthesis of D- and L-erythro-Sphingosines through Mannich-Type Reactions of N-Benzyl-2,3-O-isopropylidene-D-glyceraldehyde Nitrone. J. Org. Chem., 2006, 71, 4685-4688.
    • (2006) J. Org. Chem. , vol.71 , pp. 4685-4688
    • Merino, P.1    Jimenez, P.2    Tejero, T.3
  • 107
    • 0030691081 scopus 로고    scopus 로고
    • Diastereoselective nucleophilic addition of acetylide to N-benzyl-2,3-Oisopropylidene- D-glyceraldehyde nitrone (BIGN). Stereodivergent synthesis of 13-hydroxy-oc-(hydroxyamino)- and 13-hydroxy- o - amino acids
    • Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Diastereoselective nucleophilic addition of acetylide to N-benzyl-2,3-Oisopropylidene- D-glyceraldehyde nitrone (BIGN). Stereodivergent synthesis of 13-hydroxy-oc-(hydroxyamino)- and 13-hydroxy- o - amino acids. Tetrahedron Asymmetry, 1997, 8, 3489-3496.
    • (1997) Tetrahedron Asymmetry , vol.8 , pp. 3489-3496
    • Merino, P.1    Franco, S.2    Merchan, F.L.3    Tejero, T.4
  • 108
    • 0036939024 scopus 로고    scopus 로고
    • Facile Access to Versatile Polyaromatic Building Blocks: Selectively Protected Benzocyclobutenedione Derivatives via Regioselective [2+2] Cycloaddition of -Alkoxybenzyne and Ketene Silyl Acetal
    • Hamura, T.; Hosoya, T.; Yamaguchi, H.; Kuriyama, Y.; Tanabe, M.; Miyamoto, M.; Yasui, Y.; Matsumoto, T.; Suzuki, K. Facile Access to Versatile Polyaromatic Building Blocks: Selectively Protected Benzocyclobutenedione Derivatives via Regioselective [2+2] Cycloaddition of -Alkoxybenzyne and Ketene Silyl Acetal. Tetrahedron Asymmetry, 2002, 85, 3589-3604.
    • (2002) Tetrahedron Asymmetry , vol.85 , pp. 3589-3604
    • Hamura, T.1    Hosoya, T.2    Yamaguchi, H.3    Kuriyama, Y.4    Tanabe, M.5    Miyamoto, M.6    Yasui, Y.7    Matsumoto, T.8    Suzuki, K.9
  • 109
    • 33750465556 scopus 로고    scopus 로고
    • Efficient Synthesis of Derythro- Sphingosine and D-erythro-Azidosphingosine from D-ribo- Phytosphingosine via a Cyclic Sulfate Intermediate
    • Kim, S.; Lee, S.; Lee, T.; Ko, H.; Kim, D. Efficient Synthesis of Derythro- Sphingosine and D-erythro-Azidosphingosine from D-ribo- Phytosphingosine via a Cyclic Sulfate Intermediate. J. Org. Chem., 2006, 71, 8661-8664.
    • (2006) J. Org. Chem. , vol.71 , pp. 8661-8664
    • Kim, S.1    Lee, S.2    Lee, T.3    Ko, H.4    Kim, D.5
  • 110
    • 33750630401 scopus 로고    scopus 로고
    • Highly efficient stereoselective synthesis of d-erythro-sphingosine and d-lyxo-phytosphingosine
    • Righi, G.; Ciambrone, S.; D'Achille, C.; Leonelli, A.; Bonini, C. Highly efficient stereoselective synthesis of d-erythro-sphingosine and d-lyxo-phytosphingosine. Tetrahedron, 2006, 62, 11821-11826.
    • (2006) Tetrahedron , vol.62 , pp. 11821-11826
    • Righi, G.1    Ciambrone, S.2    D'Achille, C.3    Leonelli, A.4    Bonini, C.5
  • 111
    • 0343462456 scopus 로고    scopus 로고
    • Enantiopure Aminotriol from D-Isoascorbic Acid. Synthesis of D-Threo-C-18- Sphingosine
    • Tuch, A.; Saniere, M.; Le Merrer, Y.; Depezay, J.-C. Enantiopure Aminotriol from D-Isoascorbic Acid. Synthesis of D-Threo-C-18- Sphingosine. Tetrahedron Asymmetry, 1996, 7, 897-906.
    • (1996) Tetrahedron Asymmetry , vol.7 , pp. 897-906
    • Tuch, A.1    Saniere, M.2    Le Merrer, Y.3    Depezay, J.-C.4
  • 112
    • 33846023340 scopus 로고    scopus 로고
    • Versatile synthetic method for sphingolipids and functionalized sphingosine derivatives via olefin cross metathesis
    • Yamamoto, T.; Hasegawa, H.; Hakogi, T.; Katsumura, S. Versatile synthetic method for sphingolipids and functionalized sphingosine derivatives via olefin cross metathesis. Org. Lett., 2006, 8, 5569-5572.
    • (2006) Org. Lett. , vol.8 , pp. 5569-5572
    • Yamamoto, T.1    Hasegawa, H.2    Hakogi, T.3    Katsumura, S.4
  • 113
    • 33846813433 scopus 로고    scopus 로고
    • A concise synthesis of a promising protein kinase C inhibitor: D-erythrosphingosine
    • Pham, V. T.; Joo, J. E.; Tian, Y. S.; Oh, C. Y.; Ham, W. H. A concise synthesis of a promising protein kinase C inhibitor: D-erythrosphingosine. Arch. Pharm. Res., 2007, 30, 22-7.
    • (2007) Arch. Pharm. Res. , vol.30 , pp. 22-27
    • Pham, V.T.1    Joo, J.E.2    Tian, Y.S.3    Oh, C.Y.4    Ham, W.H.5
  • 114
    • 34547944244 scopus 로고    scopus 로고
    • A concise and scalable synthesis of high Enantiopurity (-)-D-erythro-Sphingosine Using Peptidyl Thiol Ester-Boronic Acid Cross-Coupling
    • Yang, H.; Liebeskind, L. S. A Concise and Scalable Synthesis of High Enantiopurity (-)-D-erythro-Sphingosine Using Peptidyl Thiol Ester-Boronic Acid Cross-Coupling. Org. Lett., 2007, 9, 2993-2995.
    • (2007) Org. Lett. , vol.9 , pp. 2993-2995
    • Yang, H.1    Liebeskind, L.S.2
  • 115
    • 0032800021 scopus 로고    scopus 로고
    • A new 6-hydroxy-4-sphingeninecontaining ceramide in human skin
    • Stewart, M. E.; Downing, D. T. A new 6-hydroxy-4-sphingeninecontaining ceramide in human skin. J. Lipid. Res., 1999, 40, 1434-9.
    • (1999) J. Lipid. Res. , vol.40 , pp. 1434-1439
    • Stewart, M.E.1    Downing, D.T.2
  • 116
    • 0037462337 scopus 로고    scopus 로고
    • First asymmetric synthesis of 6-Hydroxy-4-Sphingenine-Containing Ceramides. Use of chiral propargylic alcohols to prepare a lipid found in human skin
    • Chun, J.; Byun, H.-S.; Bittman, R. First Asymmetric Synthesis of 6-Hydroxy-4-Sphingenine-Containing Ceramides. Use of Chiral Propargylic Alcohols To Prepare a Lipid Found in Human Skin. J. Org. Chem., 2003, 68, 348-354.
    • (2003) J. Org. Chem. , vol.68 , pp. 348-354
    • Chun, J.1    Byun, H.-S.2    Bittman, R.3
  • 118
    • 0344845080 scopus 로고    scopus 로고
    • Synthesis and stereochemistry of ceramide B, (2S,3R,4E,6R)-N-(30-hydroxytriacontanoyl)-6-hydroxy-4- sphingenine, a new ceramide in human epidermis
    • Mori, K.; Masuda, Y. Synthesis and stereochemistry of ceramide B, (2S,3R,4E,6R)-N-(30-hydroxytriacontanoyl)-6-hydroxy-4- sphingenine, a new ceramide in human epidermis. Tetrahedron Lett., 2003, 44, 9193-9196.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 9193-9196
    • Mori, K.1    Masuda, Y.2
  • 119
    • 84986676585 scopus 로고
    • Synthesis of sphingosine relatives, X. Synthesis of (2S,3R,4E)-1-O-(β-D-glucopyranosyl)-N-[30'- (linoleoyloxy)triacontanoyl]-4-icosasphingenine, a new esterified cerebroside isolated from human and pig epidermis
    • Mori, K.; Matsuda, H. Synthesis of sphingosine relatives, X. Synthesis of (2S,3R,4E)-1-O-(β-D-glucopyranosyl)-N-[30'- (linoleoyloxy)triacontanoyl]-4-icosasphingenine, a new esterified cerebroside isolated from human and pig epidermis. Liebigs Ann. Chem., 1991, 1991, 529-535.
    • (1991) Liebigs Ann. Chem. , vol.1991 , pp. 529-535
    • Mori, K.1    Matsuda, H.2
  • 120
    • 17144465194 scopus 로고    scopus 로고
    • Synthesis of two unique compounds, a ceramide and a cerebroside, occurring in human stratum corneum
    • Müller, S.; Schmidt, R. R. Synthesis of two unique compounds, a ceramide and a cerebroside, occurring in human stratum corneum. J. Prakt. Chem., 2000, 342, 779-784.
    • (2000) J. Prakt. Chem. , vol.342 , pp. 779-784
    • Müller, S.1    Schmidt, R.R.2
  • 121
    • 0142131747 scopus 로고
    • Total synthesis of cerebrosides: (2S, 3R, 4E)-1-O-β--galactopyranosyl-N-(2βR and 2βS)-2β-hydroxytetracosanoylsphingenine
    • Koike, K.; Sugimoto, M.; Nakahara, Y.; Ogawa, T. Total synthesis of cerebrosides: (2S, 3R, 4E)-1-O-β--galactopyranosyl-N-(2βR and 2βS)-2β-hydroxytetracosanoylsphingenine. Carbohydr. Res., 1987, 162, 237-246.
    • (1987) Carbohydr. Res. , vol.162 , pp. 237-246
    • Koike, K.1    Sugimoto, M.2    Nakahara, Y.3    Ogawa, T.4
  • 122
    • 37049158564 scopus 로고
    • Wool wax. Part VI. The synthesis and stereochemistry of the straight-chain β-hydroxy-acids
    • Horn, D. H. S.; Pretorius, Y. Y. Wool wax. Part VI. The synthesis and stereochemistry of the straight-chain β-hydroxy-acids. J. Chem. Soc., 1954, 1460-1464.
    • (1954) J. Chem. Soc. , pp. 1460-1464
    • Horn, D.H.S.1    Pretorius, Y.Y.2
  • 123
    • 0000577970 scopus 로고
    • Preparation of carboxylic esters and phosphoric esters by the activation of alcohols
    • Mitsunobu, O.; Eguchi, M. Preparation of carboxylic esters and phosphoric esters by the activation of alcohols. Bull. Chem. Soc. Jpn., 1971, 44, 237-246.
    • (1971) Bull. Chem. Soc. Jpn. , vol.44 , pp. 237-246
    • Mitsunobu, O.1    Eguchi, M.2
  • 124
    • 77955610421 scopus 로고    scopus 로고
    • European Patent Office, ed
    • Van den Berg, M. A.; Streekstra, H. European Patent Office, ed., 2007; Vol. EP1767644 (A1).
    • (2007) , vol.EP1767644 , Issue.1 A
    • van den Berg, M.A.1    Streekstra, H.2
  • 125
    • 41149138766 scopus 로고    scopus 로고
    • Properties of ceramides and their impact on the stratum corneum structure. Part 2: Stratum corneum lipid model systems
    • Kessner, D.; Ruettinger, A.; Kiselev, M. A.; Wartewig, S.; Neubert, R. H. Properties of ceramides and their impact on the stratum corneum structure. Part 2: stratum corneum lipid model systems. Skin. Pharmacol. Physiol., 2008, 21, 58-74.
    • (2008) Skin. Pharmacol. Physiol. , vol.21 , pp. 58-74
    • Kessner, D.1    Ruettinger, A.2    Kiselev, M.A.3    Wartewig, S.4    Neubert, R.H.5
  • 126
    • 34147191465 scopus 로고    scopus 로고
    • Infrared spectroscopic study of stratum corneum model membranes prepared from human ceramides, cholesterol, and fatty acids
    • Gooris, G. S.; Bouwstra, J. A. Infrared spectroscopic study of stratum corneum model membranes prepared from human ceramides, cholesterol, and fatty acids. Biophys. J., 2007, 92, 2785-95.
    • (2007) Biophys. J. , vol.92 , pp. 2785-2795
    • Gooris, G.S.1    Bouwstra, J.A.2
  • 127
    • 33646878529 scopus 로고    scopus 로고
    • A novel in vitro percutaneous penetration model: Evaluation of barrier properties with paminobenzoic acid and two of its derivatives
    • de Jager, M.; Groenink, W.; Bielsa i Guivernau, R.; Andersson, E.; Angelova, N.; Ponec, M.; Bouwstra, J. A novel in vitro percutaneous penetration model: evaluation of barrier properties with paminobenzoic acid and two of its derivatives. Pharm. Res., 2006, 23, 951-60.
    • (2006) Pharm. Res. , vol.23 , pp. 951-960
    • de Jager, M.1    Groenink, W.2    Bielsa, I.3    Guivernau, R.4    Andersson, E.5    Angelova, N.6    Ponec, M.7    Bouwstra, J.8
  • 128
    • 33646878529 scopus 로고    scopus 로고
    • A Novel in Vitro Percutaneous Penetration model: Evaluation of barrier properties with P-Aminobenzoic Acid and two of its derivatives
    • de Jager, M.; Groenink, W.; Bielsa, I. G. R.; Andersson, E.; Angelova, N.; Ponec, M.; Bouwstra, J. A Novel in Vitro Percutaneous Penetration Model: Evaluation of Barrier Properties with PAminobenzoic Acid and Two of Its Derivatives. Pharm. Res., 2006.
    • (2006) Pharm. Res.
    • de Jager, M.1    Groenink, W.2    Bielsa, I.G.R.3    Andersson, E.4    Angelova, N.5    Ponec, M.6    Bouwstra, J.7
  • 130
    • 52049116882 scopus 로고    scopus 로고
    • Two new methods for preparing a unique stratum corneum substitute
    • Groen, D.; Gooris, G. S.; Ponec, M.; Bouwstra, J. A. Two new methods for preparing a unique stratum corneum substitute. Biochim. Biophys. Acta, 2008, 1778, 2421-9.
    • (2008) Biochim. Biophys. Acta , vol.1778 , pp. 2421-2429
    • Groen, D.1    Gooris, G.S.2    Ponec, M.3    Bouwstra, J.A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.