Title:
METHOD FOR PRODUCTION OF LABELED SPHINGOLIPID
Document Type and Number:
WIPO Patent Application WO/2007/102396
Kind Code:
A1
Abstract:
Disclosed is a method for production of a labeled sphingolipid, comprising reacting a sphingolipid or lysosphingolipid with an aliphatic carboxylic acid having a label selected from the group consisting of a substance capable of forming a chromophore, a fluorescent substance, biotin and a hapten by using sphingolipid ceramide N-deacylase to produce the labeled sphingolipid. The method enables to prepare any labeled sphingolipid including labeled sphingoglycolipid and labeled sphingomyelin with high efficiency and at a low cost.
Inventors:
ITO MAKOTO
YOSHIDA AI
MONJUSYO HATSUMI
OKINO NOZOMU
YOSHIDA AI
MONJUSYO HATSUMI
OKINO NOZOMU
Application Number:
PCT/JP2007/053917
Publication Date:
September 13, 2007
Filing Date:
March 01, 2007
Export Citation:
Assignee:
UNIV KYUSHU (JP)
TAKARA BIO INC (JP)
ITO MAKOTO
YOSHIDA AI
MONJUSYO HATSUMI
OKINO NOZOMU
TAKARA BIO INC (JP)
ITO MAKOTO
YOSHIDA AI
MONJUSYO HATSUMI
OKINO NOZOMU
International Classes:
C12P19/44; C12P17/16; G01N21/78; G01N33/58; C07H15/10; C12R1/01
Domestic Patent References:
| WO2002026963A1 | 2002-04-04 | |||
| WO2003093287A1 | 2003-11-13 |
Foreign References:
| JPH1081655A | 1998-03-31 | |||
| JP2002058507A | 2002-02-26 |
Other References:
SUMIDA T. ET AL.: "Molecular cloning and characterization of a novel glucocerebrosidase of Paenibacillus sp. TS12", JOURNAL OF BIOCHEMISTRY (TOKYO, JAPAN), vol. 132, no. 2, 2002, pages 237 - 243
GEGE C. ET AL.: "Synthesis of fluorescence labeled sialyl Lewisx glycosphingolipids", TETRAHEDRON LETTERS, vol. 42, no. 3, 2001, pages 377 - 380
NAKAGAWA T. ET AL.: "Preparation of fluorescence-labeled GM1 and sphingomyelin by the reverse hydrolysis reaction of sphingolipid ceramide N-deacylase as substrates for assay of sphingolipid-degrading enzymes and for detection of sphingolipid-binding proteins", JOURNAL OF BIOCHEMISTRY (TOKYO), vol. 126, no. 3, 1999, pages 604 - 611
KLAR R. ET AL.: "Synthesis of pyrenesulfonylamido-sphingomyelin and its use as substrate for determining sphingomyelinase activity and diagnosing Niemann-Pick disease", CLINICA CHIMICA ACTA, vol. 176, no. 3, 1988, pages 259 - 267
SALVAYRE R. ET AL.: "Use of mixed dispersion of fluorescent galactosylceramide and sodium dodecylsulfate for assaying galactosylceramide-beta-galactosidase and diagnosing Krabbe disease", ENZYME, vol. 33, no. 3, 1985, pages 175 - 180
HE X. ET AL.: "A fluorescence-based high-performance liquid chromatographic assay to determine acid sphingomyelinase activity and diagnose types A and B Niemann-Pick disease", ANALYTICAL BIOCHEMISTRY, vol. 314, no. 1, 2003, pages 116 - 120
BERGSTROEM F. ET AL.: "Dimers of dipyrrometheneboron difluoride (BODIPY) with light spectroscopic applications in chemistry and biology", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 124, no. 2, 2002, pages 196 - 204
BOLDYREV I.A. ET AL.: "A synthesis and properties of new 4,4-difluoro-3a,4a-diaza-s-indacene (BODIPY)-labeled lipids", RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, vol. 32, no. 1, January 2006 (2006-01-01), pages 78 - 83
MARCHESINI S. ET AL.: "Synthesis, spectral properties and enzymic hydrolysis of fluorescent derivatives of cerebroside sulfate containing long-wavelength-emission probes", CHEMISTRY AND PHYSICS OF LIPIDS, vol. 53, no. 2-3, 1990, pages 165 - 175
RON I. ET AL.: "Use of fluorescent substrates for characterization of Gaucher disease mutations", BLOOD CELLS, MOLECULES & DISEASES, vol. 35, no. 1, 2005, pages 57 - 65
GEGE C. ET AL.: "Synthesis of fluorescence labeled sialyl Lewisx glycosphingolipids", TETRAHEDRON LETTERS, vol. 42, no. 3, 2001, pages 377 - 380
NAKAGAWA T. ET AL.: "Preparation of fluorescence-labeled GM1 and sphingomyelin by the reverse hydrolysis reaction of sphingolipid ceramide N-deacylase as substrates for assay of sphingolipid-degrading enzymes and for detection of sphingolipid-binding proteins", JOURNAL OF BIOCHEMISTRY (TOKYO), vol. 126, no. 3, 1999, pages 604 - 611
KLAR R. ET AL.: "Synthesis of pyrenesulfonylamido-sphingomyelin and its use as substrate for determining sphingomyelinase activity and diagnosing Niemann-Pick disease", CLINICA CHIMICA ACTA, vol. 176, no. 3, 1988, pages 259 - 267
SALVAYRE R. ET AL.: "Use of mixed dispersion of fluorescent galactosylceramide and sodium dodecylsulfate for assaying galactosylceramide-beta-galactosidase and diagnosing Krabbe disease", ENZYME, vol. 33, no. 3, 1985, pages 175 - 180
HE X. ET AL.: "A fluorescence-based high-performance liquid chromatographic assay to determine acid sphingomyelinase activity and diagnose types A and B Niemann-Pick disease", ANALYTICAL BIOCHEMISTRY, vol. 314, no. 1, 2003, pages 116 - 120
BERGSTROEM F. ET AL.: "Dimers of dipyrrometheneboron difluoride (BODIPY) with light spectroscopic applications in chemistry and biology", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 124, no. 2, 2002, pages 196 - 204
BOLDYREV I.A. ET AL.: "A synthesis and properties of new 4,4-difluoro-3a,4a-diaza-s-indacene (BODIPY)-labeled lipids", RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, vol. 32, no. 1, January 2006 (2006-01-01), pages 78 - 83
MARCHESINI S. ET AL.: "Synthesis, spectral properties and enzymic hydrolysis of fluorescent derivatives of cerebroside sulfate containing long-wavelength-emission probes", CHEMISTRY AND PHYSICS OF LIPIDS, vol. 53, no. 2-3, 1990, pages 165 - 175
RON I. ET AL.: "Use of fluorescent substrates for characterization of Gaucher disease mutations", BLOOD CELLS, MOLECULES & DISEASES, vol. 35, no. 1, 2005, pages 57 - 65
Attorney, Agent or Firm:
HOSODA, Yoshinori (P.O. Box 26 OMM Building 5th Floor, 7-31, Otemae 1-chome, Chuo-k, Osaka-shi Osaka 91, JP)
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