SE503507C2 - Förfarande för fluorescent-märkning av sockerarter - Google Patents

Förfarande för fluorescent-märkning av sockerarter

Info

Publication number: SE503507C2
Authority: SE; Sweden
Prior art keywords: sugar; borane; reaction; complex; fluorescent
Prior art date: 1987-07-02

Application number

SE8802478A

Other languages

English (en)

Swedish (sv)

Other versions

SE8802478D0 (sv

SE8802478L (sv

Inventor

Akihiro Kondo

Ikunoshin Kato

Akira Obayashi

Sumihiro Hase

Original Assignee

Takara Shuzo Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-07-02

Filing date

1988-07-01

Publication date

1996-06-24

1988-07-01 Application filed by Takara Shuzo Co filed Critical Takara Shuzo Co

1988-07-01 Publication of SE8802478D0 publication Critical patent/SE8802478D0/xx

1989-01-03 Publication of SE8802478L publication Critical patent/SE8802478L/xx

1996-06-24 Publication of SE503507C2 publication Critical patent/SE503507C2/sv

Links

235000000346 sugar Nutrition 0.000 title claims abstract description 48
238000000034 method Methods 0.000 title claims abstract description 30
239000007850 fluorescent dye Substances 0.000 title claims abstract description 15
238000001215 fluorescent labelling Methods 0.000 title claims abstract description 11
150000008163 sugars Chemical class 0.000 title claims description 11
239000000126 substance Substances 0.000 claims abstract description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
239000002253 acid Substances 0.000 claims abstract description 9
238000002372 labelling Methods 0.000 claims abstract 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
238000006243 chemical reaction Methods 0.000 claims description 18
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical group NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 16
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 12
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 8
NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 claims description 5
GCMNJUJAKQGROZ-UHFFFAOYSA-N 1,2-Dihydroquinolin-2-imine Chemical compound C1=CC=CC2=NC(N)=CC=C21 GCMNJUJAKQGROZ-UHFFFAOYSA-N 0.000 claims description 4
229910000085 borane Inorganic materials 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 3
VEWFZHAHZPVQES-UHFFFAOYSA-N boron;n,n-diethylethanamine Chemical compound [B].CCN(CC)CC VEWFZHAHZPVQES-UHFFFAOYSA-N 0.000 claims description 2
ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 claims description 2
239000002262 Schiff base Substances 0.000 abstract 2
150000004753 Schiff bases Chemical class 0.000 abstract 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
238000004458 analytical method Methods 0.000 description 12
239000000243 solution Substances 0.000 description 8
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
238000004128 high performance liquid chromatography Methods 0.000 description 6
239000000203 mixture Substances 0.000 description 6
229930091371 Fructose Natural products 0.000 description 4
239000005715 Fructose Substances 0.000 description 4
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
230000035945 sensitivity Effects 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
102000003886 Glycoproteins Human genes 0.000 description 3
108090000288 Glycoproteins Proteins 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
238000010533 azeotropic distillation Methods 0.000 description 3
230000001605 fetal effect Effects 0.000 description 3
150000002337 glycosamines Chemical class 0.000 description 3
238000004452 microanalysis Methods 0.000 description 3
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 2
208000007976 Ketosis Diseases 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000000872 buffer Substances 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000010828 elution Methods 0.000 description 2
102000013361 fetuin Human genes 0.000 description 2
108060002885 fetuin Proteins 0.000 description 2
210000003754 fetus Anatomy 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
102000005744 Glycoside Hydrolases Human genes 0.000 description 1
108010031186 Glycoside Hydrolases Proteins 0.000 description 1
SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 1
PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 1
OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 description 1
OVRNDRQMDRJTHS-RTRLPJTCSA-N N-acetyl-D-glucosamine Chemical compound CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-RTRLPJTCSA-N 0.000 description 1
MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
150000001323 aldoses Chemical class 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
RJTANRZEWTUVMA-UHFFFAOYSA-N boron;n-methylmethanamine Chemical compound [B].CNC RJTANRZEWTUVMA-UHFFFAOYSA-N 0.000 description 1
239000012295 chemical reaction liquid Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000006862 enzymatic digestion Effects 0.000 description 1
229930182830 galactose Natural products 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002584 ketoses Chemical class 0.000 description 1
230000004140 ketosis Effects 0.000 description 1
150000002772 monosaccharides Chemical class 0.000 description 1
229920001542 oligosaccharide Polymers 0.000 description 1
150000002482 oligosaccharides Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000000941 radioactive substance Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/52—Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- G01N33/533—Production of labelled immunochemicals with fluorescent label

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Immunology (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Biomedical Technology (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Cell Biology (AREA)
Analytical Chemistry (AREA)
Microbiology (AREA)
Pathology (AREA)
Food Science & Technology (AREA)
Medicinal Chemistry (AREA)
Physics & Mathematics (AREA)
Organic Chemistry (AREA)
General Physics & Mathematics (AREA)
Genetics & Genomics (AREA)
Investigating Or Analysing Biological Materials (AREA)
Saccharide Compounds (AREA)
Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)

SE8802478A 1987-07-02 1988-07-01 Förfarande för fluorescent-märkning av sockerarter SE503507C2 (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP62163980A JPS6410177A (en)	1987-07-02	1987-07-02	Fluorescent labeling method for saccharides

Publications (3)

Publication Number	Publication Date
SE8802478D0 SE8802478D0 (sv)	1988-07-01
SE8802478L SE8802478L (sv)	1989-01-03
SE503507C2 true SE503507C2 (sv)	1996-06-24

Family

ID=15784469

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8802478A SE503507C2 (sv)	1987-07-02	1988-07-01	Förfarande för fluorescent-märkning av sockerarter

Country Status (6)

Country	Link
US (1)	US4975533A (de)
JP (1)	JPS6410177A (de)
DE (1)	DE3821809A1 (de)
FR (1)	FR2617485B1 (de)
GB (1)	GB2206691B (de)
SE (1)	SE503507C2 (de)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2761611B2 (ja) *	1992-02-22	1998-06-04	株式会社堀場製作所	分析用の前処理装置
US5548077A (en) *	1992-03-13	1996-08-20	Seikagaku Kogyo Kabushiki Kaisha	Method of producing a conjugate utilizing a 2-amino-pyridine compound
JP3122520B2 (ja) *	1992-03-13	2001-01-09	生化学工業株式会社	２−アミノピリジン誘導体、その製造方法及び蛍光標識剤
JP3020811B2 (ja) *	1993-08-23	2000-03-15	寳酒造株式会社	糖鎖構造決定方法
US5668272A (en) *	1995-06-30	1997-09-16	National Research Council Of Canada	Method for producing synthetic N-linked glycoconjugates
US5847110A (en) *	1997-08-15	1998-12-08	Biomedical Frontiers, Inc.	Method of reducing a schiff base
EP1380641A1 (de) *	2001-04-18	2004-01-14	Takara Bio Inc.	Sulfatiertes fucoglucuronomannan
ATE286075T1 (de)	2001-10-24	2005-01-15	Takara Bio Inc	Sulfatiertes fucan oligosaccharid
JP3893470B2 (ja) *	2005-03-10	2007-03-14	国立大学法人香川大学	糖類の蛍光標識化方法、糖類の蛍光標識化装置
US8283180B2 (en)	2007-04-13	2012-10-09	Amicus Therapeutics, Inc.	Periodic acid-schiff staining with detection in the infrared range
EP2282209B1 (de) *	2008-04-30	2012-10-03	Sumitomo Bakelite Company Limited	Verfahren zur markierung von zuckerketten
EP2306199A1 (de) *	2009-09-29	2011-04-06	Academisch Ziekenhuis Leiden Acting Under The Name Leiden University Medical Center	Reduktive Aminierung und Analyse von Kohlenhydraten unter Verwendung von 2-Pikolinboran als Reduktionsmittel
US9085645B2 (en)	2011-03-11	2015-07-21	Sumitomo Bakelite Co., Ltd.	Sugar chain fluorescent labeling method
CN108956792B (zh) *	2017-05-29	2020-06-16	青岛大学附属医院	血清游离甘露糖和葡萄糖的高效液相色谱检测
CN108796044B (zh) *	2018-06-12	2020-10-09	苏州百源基因技术有限公司	基于荧光标记多糖的染料编码方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4774191A (en) *	1979-09-07	1988-09-27	Syntex (U.S.A.) Inc.	Fluorescent conjugates bound to a support
US4352751A (en) *	1979-09-10	1982-10-05	Analytical Radiation Corporation	Species-linked diamine triacetic acids and their chelates
US4432907A (en) *	1979-09-10	1984-02-21	Analytical Radiation Corporation	Diamine acid fluorescent chelates
JPS60100592A (ja) *	1983-11-04	1985-06-04	Wako Pure Chem Ind Ltd	新規なオリゴ糖誘導体、並びにこれを基質として用いるα−アミラ−ゼアイソザイムの分別測定法
US4719182A (en) *	1985-03-18	1988-01-12	Eastman Kodak Company	Fluorescent labels and labeled species and their use in analytical elements and determinations

1987
- 1987-07-02 JP JP62163980A patent/JPS6410177A/ja active Granted
1988
- 1988-06-22 US US07/209,723 patent/US4975533A/en not_active Expired - Lifetime
- 1988-06-23 GB GB8814944A patent/GB2206691B/en not_active Expired - Fee Related
- 1988-06-28 DE DE3821809A patent/DE3821809A1/de active Granted
- 1988-07-01 FR FR8808954A patent/FR2617485B1/fr not_active Expired - Fee Related
- 1988-07-01 SE SE8802478A patent/SE503507C2/sv not_active IP Right Cessation

Also Published As

Publication number	Publication date
US4975533A (en)	1990-12-04
DE3821809C2 (de)	1993-03-04
GB2206691A (en)	1989-01-11
FR2617485A1 (fr)	1989-01-06
GB2206691B (en)	1991-05-15
JPH0565108B2 (de)	1993-09-17
DE3821809A1 (de)	1989-01-12
FR2617485B1 (fr)	1993-10-01
GB8814944D0 (en)	1988-07-27
SE8802478D0 (sv)	1988-07-01
SE8802478L (sv)	1989-01-03
JPS6410177A (en)	1989-01-13

Legal Events

Date	Code	Title	Description
2008-03-18	NUG	Patent has lapsed

Publication	Publication Date	Title
SE503507C2 (sv)	1996-06-24	Förfarande för fluorescent-märkning av sockerarter
US4837165A (en)	1989-06-06	Method for sequencing of peptides by carboxyl terminus degradation
Lai	1977	[26] Detection of peptides by fluorescence methods
Gros et al.	1969	Study of the dansylation reaction of amino acids, peptides and proteins
Butcher et al.	1976	Measurement of nanogram quantities of protein by hydrolysis followed by reaction with orthophthalaldehyde or determination of glutamate
EP0243429B1 (de)	1991-01-23	D-luciferin-derivate und deren verwendung
JP2021119345A5 (de)	2022-02-15
WO1998030992A2 (en)	1998-07-16	Fluorescent cyanine dyes
US4935494A (en)	1990-06-19	C-terminal peptide and protein sequencing
EP3292211B1 (de)	2025-03-12	Verfahren zur spezifischen markierung lebender mikroorganismen unter verwendung von modifizierten monosaccharidverbindungen
EP1846765B1 (de)	2009-05-27	Festphasenoligosaccharid-tagging: eine technik zur manipulation immobilisierter kohlenhydrate
Teixeira et al.	1993	Method for the analysis of oxidized nucleosides by gas chromatography mass spectrometry
Honda et al.	2000	Ultramicroanalysis of reducing carbohydrates by capillary electrophoresis with laser-induced fluorescence detection as 7-nitro-2, 1, 3-benzoxadiazole-tagged N-methylglycamine derivatives
EP2006670B1 (de)	2015-01-28	Verfahren zur veresterung eines bioverwandten moleküls für die massenspektrometrie und massenspektrometrieverfahren für das erhaltene veresterte derivat
JP4568551B2 (ja)	2010-10-27	糖たん白質糖鎖の分析方法及び非標識糖鎖の製造方法
Imai et al.	1985	Expedient chemical synthesis of sequence-specific 2', 5'-oligonucleotides
Seiler	1975	Assay procedures for polyamines and GABA in animal tissues with special reference to dansylation methods
US5182194A (en)	1993-01-26	Method for preparing p-mentha-8-thiol-3-one
Meek	1983	Derivatizing reagents for high-performance liquid chromatography detection of peptides at the picomole level
Okai et al.	1967	Resolution of amino acids. VIII. The preparation of the four optical isomers of β-hydroxyaspartic acid
van der Meer et al.	1989	Determination of PQQ in quinoproteins with covalently bound cofactor and in PQQ‐derivatives
Muraoka et al.	1999	The effects of various GTP analogues on microtubule assembly
Vorlíčková et al.	1973	Estimation of submicrogram quantities of proteins in nucleic acids samples by pulse-polarographic technique
US5859259A (en)	1999-01-12	Activated esters of 1-phenylpyrazolin-5-one for labeling amine-functionalized molecules
US5234836A (en)	1993-08-10	Method for amino acid sequence analysis