CS196962B1 - Process for preparing 14c-alpha-d-glucoso-1-phosphate with high molar radioactivity and radiochemical purity - Google Patents
Process for preparing 14c-alpha-d-glucoso-1-phosphate with high molar radioactivity and radiochemical purity Download PDFInfo
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- CS196962B1 CS196962B1 CS43578A CS43578A CS196962B1 CS 196962 B1 CS196962 B1 CS 196962B1 CS 43578 A CS43578 A CS 43578A CS 43578 A CS43578 A CS 43578A CS 196962 B1 CS196962 B1 CS 196962B1
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- glucose
- phosphate
- glucoso
- high molar
- radiochemical purity
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- 229910019142 PO4 Inorganic materials 0.000 title claims description 3
- 239000010452 phosphate Substances 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000008103 glucose Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 7
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 230000002255 enzymatic effect Effects 0.000 claims description 4
- 102000002260 Alkaline Phosphatase Human genes 0.000 claims description 3
- 108020004774 Alkaline Phosphatase Proteins 0.000 claims description 3
- DJJCXFVJDGTHFX-UHFFFAOYSA-N Uridinemonophosphate Natural products OC1C(O)C(COP(O)(O)=O)OC1N1C(=O)NC(=O)C=C1 DJJCXFVJDGTHFX-UHFFFAOYSA-N 0.000 claims description 3
- DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 claims description 3
- 238000004816 paper chromatography Methods 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 claims description 3
- 229940045145 uridine Drugs 0.000 claims description 3
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 2
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- DJJCXFVJDGTHFX-ZAKLUEHWSA-N uridine-5'-monophosphate Chemical compound O[C@@H]1[C@@H](O)[C@H](COP(O)(O)=O)O[C@H]1N1C(=O)NC(=O)C=C1 DJJCXFVJDGTHFX-ZAKLUEHWSA-N 0.000 claims 1
- 230000002485 urinary effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 229950010772 glucose-1-phosphate Drugs 0.000 description 4
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- HXXFSFRBOHSIMQ-VFUOTHLCSA-N alpha-D-glucose 1-phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O HXXFSFRBOHSIMQ-VFUOTHLCSA-N 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- DJJCXFVJDGTHFX-XVFCMESISA-N uridine 5'-monophosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H]1N1C(=O)NC(=O)C=C1 DJJCXFVJDGTHFX-XVFCMESISA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- TXXYYOUBDOAQDT-UHFFFAOYSA-N 4-nitro-1-(phenylmethoxymethyl)imidazole Chemical compound C1=NC([N+](=O)[O-])=CN1COCC1=CC=CC=C1 TXXYYOUBDOAQDT-UHFFFAOYSA-N 0.000 description 1
- 102100031126 6-phosphogluconolactonase Human genes 0.000 description 1
- 108010029731 6-phosphogluconolactonase Proteins 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000271532 Crotalus Species 0.000 description 1
- 108010018962 Glucosephosphate Dehydrogenase Proteins 0.000 description 1
- 102000005548 Hexokinase Human genes 0.000 description 1
- 108700040460 Hexokinases Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102000009617 Inorganic Pyrophosphatase Human genes 0.000 description 1
- 108010009595 Inorganic Pyrophosphatase Proteins 0.000 description 1
- 102000009569 Phosphoglucomutase Human genes 0.000 description 1
- 102000009097 Phosphorylases Human genes 0.000 description 1
- 108010073135 Phosphorylases Proteins 0.000 description 1
- FHGTVVURHLJINA-JGWLITMVSA-N [(2r,3s,4r,5r)-4,5,6-trihydroxy-1-oxo-2-phosphonooxyhexan-3-yl] dihydrogen phosphate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)C=O FHGTVVURHLJINA-JGWLITMVSA-N 0.000 description 1
- RWHOZGRAXYWRNX-VFUOTHLCSA-N alpha-D-glucose 1,6-bisphosphate Chemical compound O[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H](OP(O)(O)=O)[C@@H]1O RWHOZGRAXYWRNX-VFUOTHLCSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 238000007824 enzymatic assay Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 229940050906 magnesium chloride hexahydrate Drugs 0.000 description 1
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- -1 nucleoside diphosphates Chemical class 0.000 description 1
- 108091000115 phosphomannomutase Proteins 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Description
POPIS VYNÁLEZU (51) Int. Cl.3 C 07 H 11/04 ČESKOSLOVENSKÁ SOCIALISTICKÁ
REPUBLIKA ( 19 ) 196 962 (II) (Bl)
K AUTORSKÉMU OSVEDČENIU
(61) (23) Výstavná priorita(22) Přihlášené 23 01 7θ(21) PV 435-78
ÚŘAD PRO VYNÁLEZY
A OBJEVY (46) Zverejnené 31 07 79(45) Vydané 01 3 82 (75) \utor vynálezu
BIBLY PETER RNDr. CSc., FARKAS VLADIMÍR ing.,· CSc., BRATISLAVA aKOLBL JÁN ing., PRAHA (54)
Spdsob přípravy ^4C-oL-D-glukózo-l-fosfátu vysokej molovéj rádioaktivity a rádio-chemickej čistoty 1
Vynález sa týká spdsobu přípravy ob-D-glukózo-l-fosfátu značeného rádioaktívnym uhlí-kom * 14C vysokej molovéj rádioaktivity enzymatickou cestou a jeho izolácie z reakčnej zmesi.Vynález rieši nový postup přípravy uvedenej látky vysokej rádiochemickej čistoty a špetíi-fickej rádioaktivity. 14C-ot-D-glukózo-l-fosfát sa využívá v biochémii ako enzýmový substrát v řade reakcií,ktoré sa podieTajú na výstavbě a degradácii štrukturálnych a zásobných polysacharidov živýchbuniek rdzneho pdvodu. Stúdium mechanizmu takýchto reakcií, ako i vlastností odpovedajúcichenzýmov vyžaduje dostupnost glukózo-l-fosfátu značeného rádioaktívnymi izotopmi. Okrem to-ho 14C- oC-D-glukózo-l-fosfát sa dá využit ako medziprodukt enzýmovej alebo chemickéj synté-zy rĎznych nukleozid difosfát glukóz značených v glukózovej časti molekuly (N. K. Kochetkova V. N. Shibaev, Adv. Carb. Chem. 28. 307 (1973))· “C-ot-D-glukózo-l-fosfát sa bežne připravuje dvorná spdsobmi. Prvý spdsob, chemickásyntéza, je založený na kondenzácii peracetylovaných alebo halogénperacetylovaných derivá-tov l^C-D-glukózy s kyselinou fosforečnou, jej soTami a derivátmi v bezvodom prostředí(T. Posternak, Methods in Enzymology, Vol. 3, str. 129; L. L. McDonald, J. Org. Chem. 27.1107, 1962; Y. Y. Kusov a N. V. Shibaev, Usp. Biol. Khim. 12, 182, 1971). Uvedené chemicképostupy sú poměrně pracné a v niektorých prípadoch vedú i k tvorbě malých množstiev ft-anomé-ru glukózo-l-fosfátu, ktorý je nutné od požadovaného produktu separovat. Druhou metodou napřípravu 14C-ot-D-glukózo-l-fosfátu je enzymatická fosforolýza 14C-z«ačeného škrobu kata-196962 198 982 lyžovaná rastlinnými fosforylázami (R. M. McCready a W. Z. Zassid, Methode in Bnzymology,Vol. 3, str. 137» Academie Preaa, New York, 1957). Táto metoda vyžaduje dostupnost škrobuznačeného uhlíkom vysokej molovej rádioaktivity.
Teraz bol vypracovaný nový netradičný spčsob enzymatickéj přípravy 14C-eo-D-glukózo--1-foefátu vysokej molovej rádioaktivity, ktorý vychádza z ^^C-D-glukózy. Podstata vynálezuspočívá v tom, že ^^ff-D-glukóza sa účinkom kvasničnýeh enzýmov konvertuje na UDP-^^C-D-glu-kózu, ktorá sa priamo v pčvodnej reakčnej zmesi po odstránení rušivých látok alkalickoufosfatázou kvantitativné rozloží účinkom hádej fosfodiesterázy na uridín monofosfáta 14C- ot-D-glukózo-l-fosfát, ktorý sa z reakčnej zmesi izoluje preparatívnou papierovouChromatografiou. Posfodiesteráza štiepi UDP-^C-D.glukózu výlučné za vzniku oC-anoméru 14C--D-glukózo-l-fosfátu, čo sa potvrdilo enzymatickými testami. Produkt sa účinkom fosfogluko-mutázy konvertuje na 14C-glukózo-6-fosfát, ktorý sa identifikoval enzymaticky pomocou glu-kózo-6-fosfát dehydrogenázy. Výhodou tohto postupu přípravy 14C-eí,-D-glukózo-l-fosfátu je, že: - vychádza z 14C-D-glukózy domáceho pčvodu, - poskytuje jednoznačné ot-anomér 140-D-glukózo-l-fosfátu, - produkt sa izoluje z reakčnej zmesi jednoduchým apdsobom, papierovou chromatografiou, - všetky reakcie vedúce k produktu, počnúc od 14G-D-glukózy až po jeho chromatografickúseparáciu a čistenie, sa uskutočnujú v jedinej reakčnej nádobě, - β výnimkou niekoTkých komerčně dostupných enzýmov sa v postupe využívajú domáce suroviny, * 14 * - produkt má rovnakú molovú rádioaktivitu ako východzia C-D-glukoza. Příklad prevedenia
Reakčná zmes obsahujúca v 2,4 ml (celkový objem) 0,4 ml 0,1 M Tris-HCl pufru (pH 7,8), 1 mg ^C-D.glukózy špecifickej rádioaktivity 555 Bg/ mmol a vyššej, 12 mg trojsodnej soliuridín 5’-trifosfátu, 20 mg fosfoglycerátu sodného, 10 mg hexahydrátu chloridu horečnatého, O, 05 mg glukózo-l,6-difosfátu, 0,2 mg hexokinázy, 0,2 mg anorganickéj pyrofosfatázy a 15 mgbielkovín enzýmového preparátu připraveného z pekárenských kvašiniek podTa A. Wright a P. W. Robbins (Biochem, Biophys. Acta 104. 594, 1965) sa- inkubuje při 30 °C, kým sa nedo-siahne maximálna konverzia 14C-D-glukózy na UDP-14C-D-rglukózu. Inkubačná zmee sa potomzahřeje na 100 °C na 2 až 3 min. a po ochladení pH zmesi upraví sa nasýteným roztokomNa2COj na hodnotu zhodnú s farebným prechodom fenolftaleinu. Přidá sa 50 pl preparátualkalickej fosfatázy a po 3 až 6 hodinovej inkubácii sa zmes op&ť zahřeje na 100 °C na 2 až 3 min. Do vychladanéj zmesi, ktorej pH je zhodné s farebným prechodom fenolftaleinusa přidá 50 pl roztoku fosfodiesterázy z Crotalus terr, terr a zmes sa nechá inkubovaťpri laboratórnej teplote 2 až1 3 hodiny. Po tomto čase, ke3 sa dosiahne úplný rozklad uri-dín difosfo-^4C-D-glukózy na uridín 5’-monofosfát a 14C-et-D-glukózo-l-fosfát, sa inkubač-ná zmes zahustí na 0,5 až 1 ml a chromatografuje sa na vodou premytých papieroch Whatman 3 MM v systéme etanol - 1 M octan amónny (pH 7,3) 5 : 2 po dobu 60 až 80 hodin. Chromato-gram sa po lokalizácii uridín monofosfátu a ^C-D-glukózo-l-fosfátu dčkladne odsolí premy-
Claims (1)
- 3 196 962 tím v absolútnom etanole a acetone. 14C- ot-D-glukozo-l-fosfát sa eluuje z vysušeného chro-matogramu vodou a přečistí sa rechromatografiou za tých istých podmienok. Výtažky na vý-chodziu ^4C-D-glukozu sa pohybujú v rozmedzí 40 až 60 %. PŘED MET VYNÁLEZU TA* z Spósob přípravy C-oč-D-glukozo-l-fosfátu vysokéj molovej rádioaktivity a rádioche-mickej čistoty enzymatickou syntézou, vyznačujúci sa tým, že 14C-D-glukóza sa enzymatickyprevedie na uridín difoso-14C-D-glukózu, ktorá sa priamo v pfivodnej reakónej zmesi po· roz-klade ostatných fosforylováných derivátov alkalickou fosfatázou štiepi účinkom hádej fos-fodiesterázy na uridín 5’-monofosfát a 14C-eC-D-glukozo-l-fosfát, ktorý sa zo zmesi izolu-je papierovou chromatografiou.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS43578A CS196962B1 (en) | 1978-01-23 | 1978-01-23 | Process for preparing 14c-alpha-d-glucoso-1-phosphate with high molar radioactivity and radiochemical purity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS43578A CS196962B1 (en) | 1978-01-23 | 1978-01-23 | Process for preparing 14c-alpha-d-glucoso-1-phosphate with high molar radioactivity and radiochemical purity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS196962B1 true CS196962B1 (en) | 1980-04-30 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS43578A CS196962B1 (en) | 1978-01-23 | 1978-01-23 | Process for preparing 14c-alpha-d-glucoso-1-phosphate with high molar radioactivity and radiochemical purity |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS196962B1 (cs) |
-
1978
- 1978-01-23 CS CS43578A patent/CS196962B1/cs unknown
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