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Sphingophospholipid


DATA No : PSP6003 INFORMANT : Takehiko Yokomizo

NAME : dihydrosphingosine-1-phosphate

COMMON NAME: D-erythro-sphinganine-1-phosphate
SYMBOL: DHS-1-P/ HSPP
FORMULA: C18H40NO5P MOL.WT (average) : 381.488


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BIOLOGICAL ACTIVITY
Saturated analog of sphingosine-1-phosphate displaying 20-fold lower activity (Binds to Edg1 receptor but not functional) (Ref. 6017/6018/6019). Induces chemotaxis in HUVECs (Ref. 6018). May be used as a negative control for intracellular effects of sphingosine-1-phosphate.
Stimulate proliferation and resistance to stress in yeast (Ref. 6021/6022).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:It is difficult to suspend sphinganine-1-phosphate using organic solvents so typically it is suspended in methanol to aliquot, the methanol dried and the residue dispersed using fatty acid free BSA solution. The solubility of stock solutions may be increased by the addition of dimethylamine.
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

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OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM
Synthesized by sphinganine kinase, and dephosphorylated by sphingosine phosphatase (Ref. 6016).
GENETIC INFORMATION

NOTE

REFERENCES
[6016]
AUTHOR:Van Veldhoven, P. P., and Mannaerts, G. P.
TITLE:Sphinganine 1-phosphate metabolism in cultured skin fibroblasts: evidence for the existence of a sphingosine phosphatase PubMed ID:8192648
JOURNAL:Biochem J.
VOL:299 (Pt 3) PAGE : 597-601 (1994)
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[6017]
AUTHOR:Berger, A., Bittman, R., Schmidt, R. R., and Spiegel, S.
TITLE:Structural requirements of sphingosylphosphocholine and sphingosine-1-phosphate for stimulation of activator protein-1 activity PubMed ID:8794881
JOURNAL:Mol Pharmacol.
VOL:50 PAGE : 451-457 (1996)
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[6018]
AUTHOR:Wang, F., Van Brocklyn, J. R., Hobson, J. P., Movafagh, S., Zukowska-Grojec, Z., Milstien, S., and Spiegel, S.
TITLE:Sphingosine 1-phosphate stimulates cell migration through a G(i)-coupled cell surface receptor. Potential involvement in angiogenesis PubMed ID:10585401
JOURNAL:J Biol Chem.
VOL:274 PAGE : 35343-35350 (1999)
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[6019]
AUTHOR:Van Brocklyn, J. R., Lee, M. J., Menzeleev, R., Olivera, A., Edsall, L., Cuvillier, O., Thomas, D. M., Coopman, P. J., Thangada, S., Liu, C. H., et al.
TITLE:Dual actions of sphingosine-1-phosphate: extracellular through the Gi-coupled receptor Edg-1 and intracellular to regulate proliferation and survival PubMed ID:9660876
JOURNAL:J Cell Biol.
VOL:142 PAGE : 229-240 (1998)
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[6021]
AUTHOR:Skrzypek, M. S., Nagiec, M. M., Lester, R. L., and Dickson, R. C.
TITLE:Analysis of phosphorylated sphingolipid long-chain bases reveals potential roles in heat stress and growth control in Saccharomyces PubMed ID:9973338
JOURNAL:J Bacteriol.
VOL:181 PAGE : 1134-1140 (1999)
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[6022]
AUTHOR:Dickson, R. C., and Lester, R. L.
TITLE:Metabolism and selected functions of sphingolipids in the yeast Saccharomyces cerevisiae PubMed ID:10366774
JOURNAL:Biochim Biophys Acta.
VOL:1438 PAGE : 305-321 (1999)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.