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Long chain base and Ceramide


DATA No : DLB0241 INFORMANT : Akira Hayashi

NAME : 2S-1-Hydroxy-2-amino-octadecane-3-one

COMMON NAME: 3-Ketodihydrosphingosine / 3-Ketosphinganine
SYMBOL: KDS
FORMULA: C18H37O2N1 MOL.WT (average) : 299.492


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:Insol. in water, soluble in CHCl3 and hot EtOH
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Ubiquitous in eukaryotes (and also inlimited types of prokaryotes ) as a metabolically transient intermediate (Ref. 5001)
CHEMICAL SYNTHESIS
(Ref. 5011)
METABOLISM
3KDS is formed by condensation of L-serine with palmitoyl CoA, the reaction catalyzed by serine palmitoyltransferase (SPT) (Ref. 5002/5003); 3KDS is converted to dihydrosphingosine by 3-ketodihydrosphingosine reductase (Ref. 5002)
GENETIC INFORMATION
LCB1 and LCB2 subunits of SPT (yeast, mouse, human) (Ref. 5004/5005/5006/5007/5008/5009); 3-ketodihydrosphingosine reductase (yeast) (Ref. 5010)
NOTE

REFERENCES
[5001]
AUTHOR:Karlsson, K-A.
TITLE:On the Chemistry and Occurrence of Sphingolipid Long-Chain Bases. PubMed ID:4394487
JOURNAL:Chem. Phys. Lipids
VOL:5 PAGE : 6 -43 (1970)
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[5002]
AUTHOR:Merrill, A.H.Jr., and Sweeley, C.C. (1996) Sphingolipids:metabolism and cell signalling (Vance,D.E., and Vance,J.E., eds), pp309-339, Elsevier Science B.V., Amsterdam
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[5003]
AUTHOR:Hanada,K., Nishijima, M., and Akamatsu,Y.
TITLE:A Temperature-sensitive Mammalian Cell Mutant with Thermolabile Serine Palmitoyltransferase for the Sphingolipid Biosynthesis. PubMed ID:2125045
JOURNAL:J. Biol. Chem.
VOL:265 PAGE : 22137 -22142 (1990)
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[5004]
AUTHOR:Buede, R., Rinker-Schaffer,C., Pinto,W.J., Lester,R.L., and Dickson,R.C.
TITLE:Cloning and Characterization of LCB1,a Saccharomyces Gene Required for Biosynthesis of the Long-Chain Base Component of Sphingolipids. PubMed ID:2066332
JOURNAL:J. Bacteriology
VOL:173 PAGE : 4325 -4332 (1991)
[TOP]

[5005]
AUTHOR:Nagiec, M.M., Baltisberger, J.A., Wells, G.B., Lester, R.L., and Dickson, R.C.
TITLE:The LCB2 gene of Saccharomyces and the related LCB1 gene encode subunits of serine palmitoyltransferase, the initial enzyme in sphingolipid synthesis. PubMed ID:8058731
JOURNAL:Proc. Natl. Acad. Sci. USA
VOL:91 PAGE : 7899 -7902 (1994)
[TOP]

[5006]
AUTHOR:Zhao, C., Beeler, T., and Dunn, T.
TITLE:Suppressors of the Ca2+-sensitive Yeast Mutant(csg2) Identify Genes Involved in Sphingolipid Biosynthesis. PubMed ID:8063782
JOURNAL:J. Biol. Chem.
VOL:269 PAGE : 21480 -21488 (1994)
[TOP]

[5007]
AUTHOR:Nagiec, M.M., Lester, R.L., and Dickson, R.C.
TITLE:Sphingolipid Synthesis: Identification and Characterization of Mammalian cDNAs Encoding the Lcb2 Subunit of Serine Palmitoyltransferase. PubMed ID:8921873
JOURNAL:Gene
VOL:177 PAGE : 237 -241 (1996)
[TOP]

[5008]
AUTHOR:Hanada, K., Hara, T., Nishijima, M., Kuge, O., Dickson, R.C., and Nagiec, M.M.
TITLE:A Mammalian Homolog of the Yeast LCB1 Encodes a Component of Serine Palmitoyltransferase, the Enzyme Catalyzing the First Step in Sphingolipid Synthesis. PubMed ID:9405408
JOURNAL:J. Biol. Chem.
VOL:272 PAGE : 32108 -32114 (1997)
[TOP]

[5009]
AUTHOR:Weiss, B., and Stoffel, W.
TITLE:Human and murine serine-palmitoyl-CoA transferase:Cloning expression and characterization of the key enzyme in sphingolipid synthesis. PubMed ID:9363775
JOURNAL:Eur. J. Biochem.
VOL:249 PAGE : 239 -247 (1997)
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[5010]
AUTHOR:Beeler, T., Bacikova, D., Gable, K., Hopkins, L., Johnson, C., Slife, H., and Dunn, T.
TITLE:The Saccharomyces cerevisiae TSC10/YBR265w Gene Encoding 3-Ketosphinganine Reductase Is Identified in a Screen for Temperature-sensitive Suppressors of the Ca2+-sensitive csg2D Mutant. PubMed ID:9804843
JOURNAL:J. Biol. Chem.
VOL:273 PAGE : 30688 -30694 (1998)
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[5011]
AUTHOR:Mendershausen, P.B., and Sweeley, C.C.
TITLE:Chemistry and metabolism of sphingolipids. Chemical synthesis of 2-amino-1-hydroxyoctadecan-3-one (3-Ketosphinganine). PubMed ID:4308002
JOURNAL:Biochemistry
VOL:8 PAGE : 2633 -2635 (1969)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.