Fluorescence-labeled sphingosines as substrates of sphingosine kinases 1 and 2

被引：30

作者：

Ettmayer, P ^{[1
]}

Billich, A ^{[1
]}

Baumruker, T ^{[1
]}

Mechtcheriakova, D ^{[1
]}

Schmid, H ^{[1
]}

Nussbaumer, P ^{[1
]}

机构：

[1] Novartis Inst Biomed Res, A-1235 Vienna, Austria

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2004年 / 14卷 / 06期

关键词：

D O I：

10.1016/j.bmcl.2003.12.099

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Fluorescently labeled D-erythro-sphingosines have been successfully synthesized in 9 and 12 steps starting from commercially available Garner aldehyde. Determining the influence of the nature, position and linkage of the label on the in vitro phosphorylation rate by sphingosine kinases 1 and 2 resulted in the identification of a pyrene- and a NBD-labeled sphingosine which are both phosphorylated with efficiency comparable to the natural substrate. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：1555 / 1558

页数：4

相关论文

共 9 条

[1] Sphingolipids and the regulation of the immune response [J].

Baumruker, T ;

Prieschl, EE .

SEMINARS IN IMMUNOLOGY, 2002, 14 (01) :57-63

[2] Phosphorylation of the immunomodulatory drug FTY720 by sphingosine kinases [J].

Billich, A ;

Bornancin, F ;

Dévay, P ;

Mechtcheriakova, D ;

Urtz, N ;

Baumruker, T .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (48) :47408-47415

[3] Bioorganic chemistry of ceramide [J].

Brodesser, S ;

Sawatzki, P ;

Kolter, T .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (11) :2021-2034

[4] A STEREODIVERGENT SYNTHESIS OF D-ERYTHRO-SPHINGOSINE AND D-THREO-SPHINGOSINE FROM L-SERINE [J].

GARNER, P ;

PARK, JM ;

MALECKI, E .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) :4395-4398

[5] Synthesis of fluorescence-labeled sphingosine and sphingosine 1-phosphate; Effective tools for sphingosine and sphingosine 1-phosphate behavior [J].

Hakogi, T ;

Shigenari, T ;

Katsumura, S ;

Sano, T ;

Kohno, T ;

Igarashi, Y .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (04) :661-664

[6] Synthesis of erythro-omega-aminosphingosine and preparation of an affinity column for sphingosine kinase purification [J].

Kozikowski, AP ;

Ding, QJ ;

Spiegel, S .

TETRAHEDRON LETTERS, 1996, 37 (19) :3279-3282

[7] Sphingosine 1-phosphate signalling and termination at lipid phosphate receptors [J].

Pyne, S ;

Pyne, NJ .

BIOCHIMICA ET BIOPHYSICA ACTA-MOLECULAR AND CELL BIOLOGY OF LIPIDS, 2002, 1582 (1-3) :121-131

[8] Sphingosine-1-phosphate: An enigmatic signalling lipid [J].

Spiegel, S ;

Milstien, S .

NATURE REVIEWS MOLECULAR CELL BIOLOGY, 2003, 4 (05) :397-407

[9] Metabolism and functional effects of sphingolipids in blood cells [J].

Yang, LB ;

Yatomi, Y ;

Miura, Y ;

Satoh, K ;

Ozaki, Y .

BRITISH JOURNAL OF HAEMATOLOGY, 1999, 107 (02) :282-293