CS233088B1 - Trisododium salt of 6-(2-sulpho-4-(4-amino-3-sulpho-1-anthraquinone-amino)-aniline-4-(x-sulphoaniline)-1,3,5-triazine-2-yl-hydroxyet-hylcellulose and its preparation method - Google Patents
Trisododium salt of 6-(2-sulpho-4-(4-amino-3-sulpho-1-anthraquinone-amino)-aniline-4-(x-sulphoaniline)-1,3,5-triazine-2-yl-hydroxyet-hylcellulose and its preparation method Download PDFInfo
- Publication number
- CS233088B1 CS233088B1 CS402683A CS402683A CS233088B1 CS 233088 B1 CS233088 B1 CS 233088B1 CS 402683 A CS402683 A CS 402683A CS 402683 A CS402683 A CS 402683A CS 233088 B1 CS233088 B1 CS 233088B1
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- Czechoslovakia
- Prior art keywords
- amino
- sulfo
- hydroxyethylcellulose
- triazine
- sulpho
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- 239000004354 Hydroxyethyl cellulose Substances 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title description 4
- 229940071826 hydroxyethyl cellulose Drugs 0.000 title 1
- 150000003839 salts Chemical class 0.000 title 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 31
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 14
- 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 claims description 14
- 238000000034 method Methods 0.000 claims description 9
- 239000011780 sodium chloride Substances 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims description 2
- 238000003818 flash chromatography Methods 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 8
- YKCWQPZFAFZLBI-UHFFFAOYSA-N cibacron blue Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S(O)(=O)=O)C=C1NC(C=C1S(O)(=O)=O)=CC=C1NC(N=1)=NC(Cl)=NC=1NC1=CC=CC=C1S(O)(=O)=O YKCWQPZFAFZLBI-UHFFFAOYSA-N 0.000 description 7
- 150000004676 glycans Chemical class 0.000 description 6
- 229920001282 polysaccharide Polymers 0.000 description 6
- 239000005017 polysaccharide Substances 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920002307 Dextran Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- FYGDTMLNYKFZSV-URKRLVJHSA-N (2s,3r,4s,5s,6r)-2-[(2r,4r,5r,6s)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2r,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1[C@@H](CO)O[C@@H](OC2[C@H](O[C@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-URKRLVJHSA-N 0.000 description 1
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- 229920002498 Beta-glucan Polymers 0.000 description 1
- 229920001503 Glucan Polymers 0.000 description 1
- 229920002527 Glycogen Polymers 0.000 description 1
- 229920001612 Hydroxyethyl starch Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000001042 affinity chromatography Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 229940096919 glycogen Drugs 0.000 description 1
- 229940050526 hydroxyethylstarch Drugs 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Landscapes
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
(54) Trojsodná soí 6- [2-sulfo-4-(4-amino-3-sulfo-l-antrachinón- amino/j anilino-4-(x- sulfoanilino)-l,3,5‘-triazín-2-yl-hydroxyetylcelulózy a sposob jej přípravy(54) 6- [2-Sulfo-4- (4-amino-3-sulfo-1-anthraquinone-amino) -anilino-4- (x-sulfoanilino) -1,3,5'-triazine-2 trisodium salt -yl-hydroxyethylcellulose and a process for its preparation
233 088233 088
Vynález sa týká trojsodnej soli 6-[2-sulfo-4-(4-amino-3sulfo-l-antrachinón-amino)j anilino-4-(x-sulfoanilino)-l,3,5triazín-2-yl-hydroxyetylcelulózy a sposobu jej přípravy.The present invention relates to 6- [2-sulfo-4- (4-amino-3sulfo-1-anthraquinone-amino)] anilino-4- (x-sulfoanilino) -1,3,5-triazin-2-yl-hydroxyethylcellulose trisodium salt and how to prepare it.
Trojsodná sol 2-chlór-6-[2-sulfo-4-(4-amino-3-sulfo-lantrachinón-amino)] anilino-4-(x-sulfoanilino)-1,3,5-triazínu je farbivo, ktoré reaguje v alkalickom prostředí v rozmedzí teplót 70 až 80 °C s polysacharidmi za vzniku stálých éterických derivátov fo.F. Kennedy: Advan. Carbohyd. Chem. Biochem. 29, 305 (1974)] . Farbivo takto viazané na vhodný nerozpustný polysacharidový nosič slúži, na základe jeho interakcie s niektorými enzýmami, ako ligand v afinitnej chromatografii týchto enzýmov. z rozpustných polysacharidov derivatizovaných týmto farbivom boli připravené trojsodná sol 5-[2-sulfo-4-(4-amino-3-sulfo-l-antrachinón-amino)] anilino-4-(x-sulfoanilino)-l,3, 5-triazin-2-yl-dextránu, hydrolyzovaného škrobu, glykogénu [p. Gemeiner, 0. Mislovičová, 0. Zemek, L. Kuniak: Collect. Czech. Chem. Commun. 46, 419 (1981)J a hydroxyetylškrobu.Trisodium salt of 2-chloro-6- [2-sulfo-4- (4-amino-3-sulfo-lanthraquinone-amino)] anilino-4- (x-sulfoanilino) -1,3,5-triazine is a dye that reacts in an alkaline medium between 70 and 80 ° C with polysaccharides to form stable ether derivatives of fo.F. Kennedy: Advan. Carbohyd. Chem. Biochem. 29, 305 (1974)]. The dye thus bound to a suitable insoluble polysaccharide carrier serves as a ligand in the affinity chromatography of these enzymes, due to its interaction with some enzymes. from the soluble polysaccharides derivatized with this dye, the trisodium salt of 5- [2-sulfo-4- (4-amino-3-sulfo-1-anthraquinone-amino)] anilino-4- (x-sulfoanilino) -1,3,5 was prepared -triazin-2-yl-dextran, hydrolyzed starch, glycogen [p. Gemeiner, 0. Mislovic, 0. Zemek, L. Kuniak: Collect. Czech. Chem. Commun. 46, 419 (1981) J and hydroxyethyl starch.
Všetky tieto polysacharidy sú vetvené cC-glukány, na rozdiel od hydroxyetylcelulózy, ktorá je /3-glukán s lineárnym reťazcom.All these polysaccharides are branched c-glucanes, unlike hydroxyethylcellulose, which is a β-glucan with a linear chain.
Podmienky reakcie hydroxyetylcelulózy s trojsodnou solou 2-chlór-6-[2-sulfo-4-(4-amino-3-sulfo-l-antrachinón-amino)] anilino-4-(x-sulfoanilino)-1,3,5-triazínom sa líšia od podmienok farbenia dextránov[p. Gemeiner a kol.: Collect. Czech. Chem. Commun, 46, 419 (1981)] tým, že sú miernejsie ale sa pri nich dosiahne rovnaký stupeň substitúcie. Oe to spósobené váčšou reaktivitou hydroxyetylcelulózy v důsledku přítomnosti váčšieho množstva primárné alkoholických skupin, ktoré reagujú přednostně. Pri izolácii ziskanej trojsodnej soli 6-[2-sulfo-.4-(4-amino-sulfo-l-antrachinón-amino)J anilino-4-( x-sulfoanilino)-1,3,5-triazin-2-yl-hydroxyetylcelulózy nie je možné priConditions of reaction of hydroxyethylcellulose with trisodium salt of 2-chloro-6- [2-sulfo-4- (4-amino-3-sulfo-1-anthraquinone-amino)] anilino-4- (x-sulfoanilino) -1,3,5 -triazine differs from dextran staining conditions [p. Gemeiner et al., Collect. Czech. Chem. Commun, 46, 419 (1981)] by being milder but achieving the same degree of substitution. This is due to the greater reactivity of the hydroxyethylcellulose due to the presence of a greater amount of primary alcohol groups which react preferentially. In the isolation of the obtained trisodium salt of 6- [2-sulfo-4- (4-amino-sulfo-1-anthraquinone-amino)] anilino-4- (x-sulfoanilino) -1,3,5-triazin-2-yl - hydroxyethylcellulose is not possible with
- 3 233 088 molekulových hmotnostiach nad 100 000 použiť metodu gélovej chroraatografie pre velmi vysokú viskozitu roztoku tejto zlúčeniny.- 3,233,088 molecular weights above 100,000 to use the gel chromatography method for the very high viscosity of the solution of this compound.
Uvedený problém rieši tento vynález. Podstatou vynálezu je trojsodná soX 6-[2-sulfo-4-(4-aminO“Sulfo-l-antrachinónamino)J anilino-4-(x-sulfoanilino)-1,3,5-triazxn-2-yl-hydroxyetylcelulózy, kde x je poloha substituenta 2 alebo 4 vzorca IThe present invention solves this problem. The present invention provides the trisodium salt of 6- [2-sulfo-4- (4-amino-sulfon-1-anthraquinonamino)] anilino-4- (x-sulfoanilino) -1,3,5-triazin-2-yl-hydroxyethylcellulose, wherein x is the position of substituent 2 or 4 of formula I
kde R představuje hydroxyetylcelulózu so stupňom substitúciewherein R represents hydroxyethylcellulose with a degree of substitution
2,5 a priememej molekulovej hmotnosti 2.104 až 5,4.105. Ďalej podstatou vynálezu je spósob přípravy týchto derivátov, ktorý sa vyznačuje tým, že jednotlivé frakcie hydroxyetylcelulózy reagujú vo vodnom alkalickom prostředí a za přítomnost i 1,7 % chloridu sodného pri teplote 70 až 80 °C a počas dvoch hodin s trojsodnou solou 2-chlór-6~[2-sulfo-4-(4-amino-3-sulfo-l-antrachinón-amino)J anilino-4-(x-sulfoanilino)-1,3 ,5-triazxnu vzorca II pri váhových pomeroch trojsodná sol 2-chlór-6-2.5 and average molecular weight 2.10 4 to 5.4.10 5 . The invention further provides a process for the preparation of these derivatives, characterized in that the individual fractions of hydroxyethylcellulose are reacted in an aqueous alkaline medium and in the presence of 1.7% sodium chloride at a temperature of 70 to 80 ° C and for 2 hours with trisodium salt. -6- [2-sulfo-4- (4-amino-3-sulfo-1-anthraquinone-amino)] anilino-4- (x-sulfoanilino) -1,3,5-triazine of formula II at weight ratios trisodium salt 2-chloro-6-
233 088233 088
- [2-sulfo-4-(4-amino~3-sulfo-l-antrachinón-amino j] anilino-4-(x-sulfoanilino)-1,3,5-triazínu : hydroxyetylcelulóza : uhličitan sodný = 0,2 až 0,32 : 1 : 0,54 až 0,59, načo sa zafarbená hydroxyetylcelulóza oddělí od nenaviazaného farbiva bu3 gólovou chromatografiou (do priemernej molekulovej hmotnosti Mw 100 000) alebo 6 až 7 násobným zrážaním a následnou centrifugáciou z 0,5 % vodného roztoku chloridu sodného (nad Mw 100 000).- [2-sulfo-4- (4-amino-3-sulfo-1-anthraquinone-amino)] anilino-4- (x-sulfoanilino) -1,3,5-triazine: hydroxyethylcellulose: sodium carbonate = 0.2 up to 0.32: 1: 0.54 to 0.59, whereupon the stained hydroxyethylcellulose is separated from the unbound dye by either flash chromatography (up to an average molecular weight Mw of 100,000) or by 6 to 7 fold precipitation followed by centrifugation from 0.5% aqueous sodium chloride solution (above Mw 100 000).
Výhodou navrhovaného spósobu přípravy trojsodnej soli 6-[2-sulfo-4-(4-amino-3-sulfo-l-antrachinón-amino)] anilino-4-(x-sulfoanilino)-1,3,5-triazín-2-yl-hydroxyetylcelulózy je, že poskytuje farebné deriváty vodorozpustného polysacharidu s lineárnou strukturou t.j. hydroxyetylcelulózy, ktoré sú vhodné pre štúdium interakcie farebného polysacharidu s enzýmom. Ďalšou výhodou je spósob izolácie tejto látky z reakčnej zmesi na základe jej nerozpustnosti v roztoku solí v 50 až 60 % výtažku.The advantage of the proposed process for the preparation of the trisodium salt of 6- [2-sulfo-4- (4-amino-3-sulfo-1-anthraquinone-amino)] anilino-4- (x-sulfoanilino) -1,3,5-triazine-2 -yl-hydroxyethylcellulose is that it provides colored derivatives of water-soluble polysaccharide with a linear structure ie hydroxyethylcelluloses which are useful for studying the interaction of a colored polysaccharide with an enzyme. A further advantage is the method of isolating this material from the reaction mixture because of its insolubility in the salt solution in 50 to 60% yield.
Příklad 1 mg hydroxyetylcelulózy (HEC) o priemernej molekulovej hmotnosti (Mw) 350 000 sa rozpustí v 2 ml destilovanej vody pri teplote 60 °C. Potom sa přidá 7 mg trojsodnej soli 2-chlór-6-(2-sulfo-4-(4-amino-3-sulfo-l-ant rachinón-amino)] anilino-4-(x-sulfoanilino)-1,3 ,5-triazínu (Cibacron Blue 3G-A) rozpustenej v 0,2 ml destilovanej vody. Reakčná zmes sa mieša pri teplote 60 °C po dobu 30 min. Potom sa přidá 43,75 mg chloridu sodného a pokračuje sa v miešaní ešte po dobu 30 min. Po zvýšeni teploty na 80 °C sa přidá 15 mg uhličitanu sodného rozpuštěného v 0,05 ml destilovanej vody a reakčná zmes sa mieša ešte po dobu 2 h. Po ochladení sa reakčná zmes zriedi s 20 ml destilovanej vody a zneutralizuje zriedenou kyselinou chlorovodíkovou na pH 7. Zafarbená hydroxyetylcelulóza sa vyzráža přidáním 20 ml 1 % vodného roztoku chloridu sodného a ochladením na teplotu 4 °C. Zrazenina sa odcentrifuguje pri 4.10 otáčkách za min. Supernatant sa oddělí a zrazenina sa rozpusti v 20 ml destilovanej vody pri teplote 50 °C. Z roztoku sa Cibacron Blue-HEC znovu vyzráža s 20 ml 1 % vodného roztoku chloridu sodného pri teplote 4 °C a znovu odcentrifuguje. Toto sa opakuje 6 krát, až kým je supernatant bezfarebný. Získaná Cibacron Blue-HEC sa rozpustí v 20 ml destilovanej vody a dialyzuje po dobu 24 h protiExample 1 mg of hydroxyethylcellulose (HEC) with an average molecular weight (Mw) of 350,000 is dissolved in 2 ml of distilled water at 60 ° C. 7 mg of 2-chloro-6- (2-sulfo-4- (4-amino-3-sulfo-1-anthroquinone-amino)] anilino-4- (x-sulfoanilino) -1,3 trisodium salt is then added. 5-triazine (Cibacron Blue 3G-A) dissolved in 0.2 mL of distilled water The reaction mixture is stirred at 60 ° C for 30 min, then 43.75 mg of sodium chloride is added and stirring is continued After raising the temperature to 80 ° C, 15 mg of sodium carbonate dissolved in 0.05 ml of distilled water are added and the reaction mixture is stirred for a further 2 h. After cooling, the reaction mixture is diluted with 20 ml of distilled water and neutralized with dilute water. hydrochloric acid to pH 7. The colored hydroxyethylcellulose is precipitated by adding 20 ml of 1% aqueous sodium chloride solution and cooling to 4 DEG C. The precipitate is centrifuged at 4.10 rpm and the supernatant is separated and the precipitate is dissolved in 20 ml of distilled water at 50 DEG C. Cibacron Blue-HEC is reprecipitated from the solution with 20 ml of 1% aq of sodium chloride at 4 ° C and centrifuged again. This is repeated 6 times until the supernatant is colorless. The obtained Cibacron Blue-HEC is dissolved in 20 ml of distilled water and dialyzed for 24 h against
233 088 destilovanej vodě. Po oddělení nerozpustných podielov odfiltrováním sa získaný modrý roztok odpaří na vákuovej rotačnej odparke do sucha pri tlaku 5 kPa* po přidaní a znovu odpaření etanolu a potom acetonu sa získá suchý Cibacron Blue-HEC (15,2 mg) s obsahom 68 yumólu Cibacron Blue-HEC/g.233 088 distilled water. After separation of the insolubles by filtration, the resulting blue solution is evaporated to dryness in a vacuum rotary evaporator at 5 kPa * after addition and re-evaporation of ethanol and then acetone to give a dry Cibacron Blue-HEC (15.2 mg) containing 68 yumole of Cibacron Blue- HEC / g.
Přiklad 2Example 2
Postup podlá příkladu 1 s tým rozdielom, že sa použije HEC (Mw = 41 OOO) a 6,6 mg farbiva Cibacron Blue 3G-A, Zafarbená HEC sa oddělí od nenaviazaného farbiva na koloně naplnenej dextránom sieťovaným epichlórhydrínom (Sephadex G-25 fine). Objem náplně kolony je 100 ml, výška 21,5 cm a priemer 2,5 cm. Eluuje sa destilovanou vodou, pri prietoku eluátu kolonou 30 až 35 ml/h Ziska sa suchý Cibacron Blue-HEC (21 mg) s obsahom 79,3 yumólu Cibacron Blue/g.The procedure of Example 1 except that HEC (Mw = 41,000) and 6.6 mg of Cibacron Blue 3G-A was used. . The column volume is 100 ml, 21.5 cm high and 2.5 cm diameter. Elute with distilled water, eluting with a column flow of 30 to 35 ml / h to obtain dry Cibacron Blue-HEC (21 mg) containing 79.3 yumole Cibacron Blue / g.
Příklad 3Example 3
Postup podlá příkladu 1 s tým rozdielom, že sa použije HEC (Mw = 540 000) a 6,6 mg farbiva Cibacron Blue 3G-A. Získá sa suchý Cibacron Blue-HEC (17,8 mg) s obsahom 60,6 yuroólu Cibacron Blue/g.The procedure of Example 1 except that HEC (Mw = 540,000) and 6.6 mg of Cibacron Blue 3G-A was used. Dry Cibacron Blue-HEC (17.8 mg) was obtained containing 60.6 yuroole of Cibacron Blue / g.
Příklad 4Example 4
Postup podlá příkladu 1 s tým rozdielom, že sa použije HEC (Mw 350 000, 8 mg farbiva Cibacron Blue 3G-A a teplota 70 °C. Získá sa suchý Cibacron Blue-HEC (16,5 mg) s obsahom 65,4 ^umól Cibacron Blue/g.The procedure of Example 1 was followed except that HEC (Mw 350,000, 8 mg of Cibacron Blue 3G-A and 70 ° C) was obtained to obtain a dry Cibacron Blue-HEC (16.5 mg) containing 65.4%. umol Cibacron Blue / g.
Vynález má využitie v enzýmovom inžxnierstve a v biochémii a to pri izolácii a purifikácii enzýmov alebo ako substráty a inhibitory enzýmami katalyzovaných reakcii.The invention has utility in enzyme engineering and in biochemistry for the isolation and purification of enzymes or as substrates and inhibitors of enzyme-catalyzed reactions.
PREDMET VYNÁLEZUOBJECT OF THE INVENTION
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS402683A CS233088B1 (en) | 1983-06-03 | 1983-06-03 | Trisododium salt of 6-(2-sulpho-4-(4-amino-3-sulpho-1-anthraquinone-amino)-aniline-4-(x-sulphoaniline)-1,3,5-triazine-2-yl-hydroxyet-hylcellulose and its preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS402683A CS233088B1 (en) | 1983-06-03 | 1983-06-03 | Trisododium salt of 6-(2-sulpho-4-(4-amino-3-sulpho-1-anthraquinone-amino)-aniline-4-(x-sulphoaniline)-1,3,5-triazine-2-yl-hydroxyet-hylcellulose and its preparation method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS233088B1 true CS233088B1 (en) | 1985-02-14 |
Family
ID=5382041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS402683A CS233088B1 (en) | 1983-06-03 | 1983-06-03 | Trisododium salt of 6-(2-sulpho-4-(4-amino-3-sulpho-1-anthraquinone-amino)-aniline-4-(x-sulphoaniline)-1,3,5-triazine-2-yl-hydroxyet-hylcellulose and its preparation method |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS233088B1 (en) |
-
1983
- 1983-06-03 CS CS402683A patent/CS233088B1/en unknown
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