JPH0255434B2 - - Google Patents
Info
- Publication number
- JPH0255434B2 JPH0255434B2 JP188480A JP188480A JPH0255434B2 JP H0255434 B2 JPH0255434 B2 JP H0255434B2 JP 188480 A JP188480 A JP 188480A JP 188480 A JP188480 A JP 188480A JP H0255434 B2 JPH0255434 B2 JP H0255434B2
- Authority
- JP
- Japan
- Prior art keywords
- biopterin
- hydroxy
- water
- amino
- ria
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- HNXQXTQTPAJEJL-UHFFFAOYSA-N 2-aminopteridin-4-ol Chemical class C1=CN=C2NC(N)=NC(=O)C2=N1 HNXQXTQTPAJEJL-UHFFFAOYSA-N 0.000 claims description 16
- -1 dihydroxypropyl Chemical group 0.000 claims description 5
- 230000002285 radioactive effect Effects 0.000 claims description 5
- 239000000700 radioactive tracer Substances 0.000 claims description 5
- 238000003556 assay Methods 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 18
- LHQIJBMDNUYRAM-AWFVSMACSA-N D-erythro-biopterin Chemical compound N1=C(N)NC(=O)C2=NC([C@H](O)[C@H](O)C)=CN=C21 LHQIJBMDNUYRAM-AWFVSMACSA-N 0.000 description 14
- LHQIJBMDNUYRAM-UHFFFAOYSA-N L-erythro-Biopterin Natural products N1=C(N)NC(=O)C2=NC(C(O)C(O)C)=CN=C21 LHQIJBMDNUYRAM-UHFFFAOYSA-N 0.000 description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229940098773 bovine serum albumin Drugs 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000003127 radioimmunoassay Methods 0.000 description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 6
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 6
- 210000002700 urine Anatomy 0.000 description 6
- 241000473945 Theria <moth genus> Species 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000008363 phosphate buffer Substances 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 4
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 4
- 238000002372 labelling Methods 0.000 description 4
- BMQYVXCPAOLZOK-XINAWCOVSA-N neopterin Chemical compound OC[C@@H](O)[C@@H](O)C1=CN=C2NC(N)=NC(=O)C2=N1 BMQYVXCPAOLZOK-XINAWCOVSA-N 0.000 description 4
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WDRISBUVHBMJEF-YUPRTTJUSA-N (2r,3s,4s)-2,3,4-trihydroxypentanal Chemical compound C[C@H](O)[C@H](O)[C@@H](O)C=O WDRISBUVHBMJEF-YUPRTTJUSA-N 0.000 description 3
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- BMQYVXCPAOLZOK-UHFFFAOYSA-N Trihydroxypropylpterisin Natural products OCC(O)C(O)C1=CN=C2NC(N)=NC(=O)C2=N1 BMQYVXCPAOLZOK-UHFFFAOYSA-N 0.000 description 3
- DZGWFCGJZKJUFP-UHFFFAOYSA-N Tyramine Natural products NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 3
- 229960002684 aminocaproic acid Drugs 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000002649 immunization Methods 0.000 description 3
- 230000003053 immunization Effects 0.000 description 3
- 230000016784 immunoglobulin production Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 229960003732 tyramine Drugs 0.000 description 3
- DZGWFCGJZKJUFP-UHFFFAOYSA-O tyraminium Chemical compound [NH3+]CCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-O 0.000 description 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- XKAYRHLZQHITSP-UHFFFAOYSA-N 6-amino-2-methylsulfanyl-5-nitroso-1h-pyrimidin-4-one Chemical compound CSC1=NC(=O)C(N=O)=C(N)N1 XKAYRHLZQHITSP-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 229920000298 Cellophane Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- FEMXZDUTFRTWPE-DZSWIPIPSA-N L-erythro-7,8-dihydrobiopterin Chemical compound N1C(N)=NC(=O)C2=C1NCC([C@@H](O)[C@@H](O)C)=N2 FEMXZDUTFRTWPE-DZSWIPIPSA-N 0.000 description 2
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 238000004166 bioassay Methods 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 2
- 230000009260 cross reactivity Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229960000304 folic acid Drugs 0.000 description 2
- 235000019152 folic acid Nutrition 0.000 description 2
- 239000011724 folic acid Substances 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- FNKQXYHWGSIFBK-RPDRRWSUSA-N sapropterin Chemical compound N1=C(N)NC(=O)C2=C1NC[C@H]([C@@H](O)[C@@H](O)C)N2 FNKQXYHWGSIFBK-RPDRRWSUSA-N 0.000 description 2
- 229960004617 sapropterin Drugs 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 229940001584 sodium metabisulfite Drugs 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- AUAHIQMUUCDLNZ-UHFFFAOYSA-N 2-(dimethylamino)-1h-pteridin-4-one Chemical compound C1=CN=C2NC(N(C)C)=NC(=O)C2=N1 AUAHIQMUUCDLNZ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- BMQYVXCPAOLZOK-UJURSFKZSA-N 2-amino-6-[(1r,2s)-1,2,3-trihydroxypropyl]-1h-pteridin-4-one Chemical compound OC[C@H](O)[C@H](O)C1=CN=C2NC(N)=NC(=O)C2=N1 BMQYVXCPAOLZOK-UJURSFKZSA-N 0.000 description 1
- XGXBEYPTWXSMTE-UHFFFAOYSA-N 2-methylsulfanyl-1h-pteridin-4-one Chemical compound C1=CN=C2NC(SC)=NC(=O)C2=N1 XGXBEYPTWXSMTE-UHFFFAOYSA-N 0.000 description 1
- VWNVTVHTUBZECM-UHFFFAOYSA-N 2-methylsulfanyl-5-nitrosopyrimidine Chemical compound CSC1=NC=C(N=O)C=N1 VWNVTVHTUBZECM-UHFFFAOYSA-N 0.000 description 1
- NLMMAGYRLCJHCC-UHFFFAOYSA-N 6-[(5,6-diamino-4-oxo-1h-pyrimidin-2-yl)amino]hexanoic acid;hydrate;dihydrochloride Chemical compound O.Cl.Cl.NC1=NC(NCCCCCC(O)=O)=NC(O)=C1N NLMMAGYRLCJHCC-UHFFFAOYSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 208000027219 Deficiency disease Diseases 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinopyranose Chemical compound O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 201000011252 Phenylketonuria Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
- 230000037354 amino acid metabolism Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000011587 new zealand white rabbit Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 150000003195 pteridines Chemical class 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP188480A JPS5699484A (en) | 1980-01-11 | 1980-01-11 | Pterin derivative and determination of pterins |
| GB8021637A GB2056459B (en) | 1979-07-04 | 1980-07-02 | Pterin derivatives and an assay method for determining pterins |
| NL8003854A NL8003854A (nl) | 1979-07-04 | 1980-07-03 | Pteridinederivaten en radio-immunologische bepalingsmethode. |
| SE8004933A SE441529B (sv) | 1979-07-04 | 1980-07-03 | Radioimmunoanalys av pteriner och nya pterinderivat lempade for detta endamal |
| DE3025226A DE3025226C2 (de) | 1979-07-04 | 1980-07-03 | Pterinderivate und ihre Verwendung zur radioimmunologischen Bestimmung von Pterinen |
| FR8014984A FR2460952A1 (fr) | 1979-07-04 | 1980-07-04 | Procede de determination radioimmunologique de pterines et nouveaux derives de pterine utiles dans ce procede |
| AU60106/80A AU526214B2 (en) | 1979-07-04 | 1980-07-04 | Pteridin derivatives |
| CA000355429A CA1150243A (en) | 1979-07-04 | 1980-07-04 | Radioimmunoassay of pterins and novel pterin derivatives useful therefor |
| US06/166,519 US4371514A (en) | 1979-07-04 | 1980-07-07 | Radioimmunoassay of pterins and novel pterin derivatives useful therefor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP188480A JPS5699484A (en) | 1980-01-11 | 1980-01-11 | Pterin derivative and determination of pterins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5699484A JPS5699484A (en) | 1981-08-10 |
| JPH0255434B2 true JPH0255434B2 (enrdf_load_stackoverflow) | 1990-11-27 |
Family
ID=11513986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP188480A Granted JPS5699484A (en) | 1979-07-04 | 1980-01-11 | Pterin derivative and determination of pterins |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5699484A (enrdf_load_stackoverflow) |
-
1980
- 1980-01-11 JP JP188480A patent/JPS5699484A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5699484A (en) | 1981-08-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4399121A (en) | Iodothyronine immunogens and antibodies | |
| US4213893A (en) | Flavin adenine dinucleotide-labeled conjugates for use in specific binding assays | |
| US4302438A (en) | Antigen, antiserum and immunoassay for theophylline | |
| JPS5928864B2 (ja) | バルビツ−ル酸抗原およびそれに対して特異な抗体 | |
| JPH0231825B2 (enrdf_load_stackoverflow) | ||
| US4478934A (en) | Determination of adenosine by immunoassay involving acylation of the adenosine | |
| JPH09504505A (ja) | プテリン誘導体およびその製法と利用法 | |
| US4371514A (en) | Radioimmunoassay of pterins and novel pterin derivatives useful therefor | |
| US20070148700A1 (en) | Site-specific aminoglycoside derivatives for use in immunodiagnostic assays | |
| JPH0331226B2 (enrdf_load_stackoverflow) | ||
| US20170362579A1 (en) | Conjugates for assays for oxycodone and oxymorphone | |
| CA1128883A (en) | Flavin adenine dinucleotide - labeled conjugates for use in specific binding assays | |
| JPH0255434B2 (enrdf_load_stackoverflow) | ||
| JPS6084297A (ja) | 新規なアミノプリン誘導体 | |
| JPH0262820B2 (enrdf_load_stackoverflow) | ||
| JPH0231720B2 (ja) | Puterinjudotaioyobiputerinruinosokuteiho | |
| JPH0259151B2 (enrdf_load_stackoverflow) | ||
| Nagatsu et al. | Radioimmunoassay for biopterin | |
| JPH0631309B2 (ja) | 新規２′―５′オリゴアデニル酸化合物およびその製造方法 | |
| CA1139303A (en) | Flavin adenine dinucleotide-labeled conjugates for use in specific binding assays | |
| Singh et al. | Specific Antibodies to Theophylline for Use in a Homogeneous: Enzyme Immunoassay | |
| JPH0317300B2 (enrdf_load_stackoverflow) | ||
| JP2926767B2 (ja) | モルヒネの測定キットおよび測定法 | |
| CA1137981A (en) | 6-(.omega.-AMINOALKYL)-9-(2',3'-O-ISOPROPYLIDINE- .beta.-D-RIBOFURANOSYL)PURINES | |
| JPS58221168A (ja) | アラビノヌクレオシドの定量法 |