CS231544B1 - Processing of l-glucose and l-manose - Google Patents
Processing of l-glucose and l-manose Download PDFInfo
- Publication number
- CS231544B1 CS231544B1 CS833908A CS390883A CS231544B1 CS 231544 B1 CS231544 B1 CS 231544B1 CS 833908 A CS833908 A CS 833908A CS 390883 A CS390883 A CS 390883A CS 231544 B1 CS231544 B1 CS 231544B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- glucose
- mannose
- ethyl alcohol
- arabinose
- mixture
- Prior art date
Links
- GZCGUPFRVQAUEE-VANKVMQKSA-N aldehydo-L-glucose Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)C=O GZCGUPFRVQAUEE-VANKVMQKSA-N 0.000 title 1
- WQZGKKKJIJFFOK-ZZWDRFIYSA-N L-glucose Chemical compound OC[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-ZZWDRFIYSA-N 0.000 claims abstract description 29
- WQZGKKKJIJFFOK-JFNONXLTSA-N L-mannopyranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-JFNONXLTSA-N 0.000 claims abstract description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- 235000019441 ethanol Nutrition 0.000 claims abstract description 13
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims abstract description 11
- SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinopyranose Chemical compound O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-N 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 9
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims abstract description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001768 cations Chemical class 0.000 claims abstract description 6
- 239000003480 eluent Substances 0.000 claims abstract description 5
- 230000002378 acidificating effect Effects 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims 1
- 230000003851 biochemical process Effects 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 239000002777 nucleoside Substances 0.000 abstract description 3
- 125000003835 nucleoside group Chemical group 0.000 abstract description 3
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 238000004042 decolorization Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- HOFCJTOUEGMYBT-BXKVDMCESA-N (2s,3s,4s,5s)-6-nitrohexane-1,2,3,4,5-pentol Chemical class OC[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C[N+]([O-])=O HOFCJTOUEGMYBT-BXKVDMCESA-N 0.000 description 5
- 235000000346 sugar Nutrition 0.000 description 5
- HOFCJTOUEGMYBT-VANKVMQKSA-N (2s,3s,4s,5r)-6-nitrohexane-1,2,3,4,5-pentol Chemical class OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)C[N+]([O-])=O HOFCJTOUEGMYBT-VANKVMQKSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000008163 sugars Chemical class 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000001323 aldoses Chemical class 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 3
- 229940067157 phenylhydrazine Drugs 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- -1 molybdate ions Chemical class 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LWFUFLREGJMOIZ-UHFFFAOYSA-N 3,5-dinitrosalicylic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O LWFUFLREGJMOIZ-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- PYMYPHUHKUWMLA-VAYJURFESA-N aldehydo-L-arabinose Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-VAYJURFESA-N 0.000 description 1
- GZCGUPFRVQAUEE-BXKVDMCESA-N aldehydo-L-mannose Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-BXKVDMCESA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Abstract
Vynález sa týká sposobu přípravy L-glukózy a L-manózy. Podstata vynálezu spočívá v tom, že sa zmes L-glukózy, L-manózy a L-arabinózy, ktorá vzniká pri nitrometanove] syntéze z L-arabinózy selektívne rozdělí pomocou silné kyslého vymieňača katiónov vo vápenatej formě. Ako eluačné činidlo sa použije 40 až 60 % vodný roztok etylálkoholu. Čisté frakcie L-glukóza a L- -manóza sa po zahuštění a odfarbení aktívnym uhlím jednotlivé zahustia na rotačnej odparke a z etylálkoholu vykryštalizujú. Vynález má rozsiahle použitie pri štúdiu biochemických pochodov, v medicíně, pri přípravě nových nukleozidovThe present invention relates to a process for preparing L-glucose and L-mannose. The essence of the invention resides in that a mixture of L-glucose, L-mannose is formed and L-arabinose produced by nitromethane] synthesis from L-arabinose selectively divides using a strong acidic cation exchanger in calcium form. As eluent 40-60% aqueous solution is used ethyl alcohol. Pure L-glucose and L- -manosis is active after concentration and decolorization the individual coalesce to rotary evaporator and crystallized from ethyl alcohol. The invention has extensive use in the study biochemical processes, in medicine, at preparation of new nucleosides
Description
Vynález sa týká sposobu přípravy L-glukózy a L-manózy. Podstata vynálezu spočívá v tom, že sa zmes L-glukózy, L-manózy a L-arabinózy, ktorá vzniká pri nitrometanove] syntéze z L-arabinózy selektívne rozdělí pomocou silné kyslého vymieňača katiónov vo vápenatej formě. Ako eluačné činidlo sa použije 40 až 60 % vodný roztok etylálkoholu. Čisté frakcie L-glukóza a L-manóza sa po zahuštění a odfarbení aktívnym uhlím jednotlivé zahustia na rotačnej odparke a z etylálkoholu vykryštalizujú.The invention relates to a process for preparing L-glucose and L-mannose. SUMMARY OF THE INVENTION The present invention is characterized in that the mixture of L-glucose, L-mannose and L-arabinose resulting from nitromethane synthesis from L-arabinose is selectively separated by a strong acid cation exchanger in calcium form. A 40-60% aqueous ethyl alcohol solution was used as eluent. The pure L-glucose and L-mannose fractions are individually concentrated on a rotary evaporator after concentration and decolourisation with activated carbon and crystallized from ethyl alcohol.
Vynález má rozsiahle použitie pri štúdiu biochemických pochodov, v medicíně, pri přípravě nových nukleozidov.The invention has extensive application in the study of biochemical processes, in medicine, in the preparation of new nucleosides.
Vynález sa týká přípravy kryštalickej L-glukózy a L-manózy zo zmesi cukrov po nitrometanovej syntéze L-arabinózy.The invention relates to the preparation of crystalline L-glucose and L-mannose from a mixture of sugars after nitromethane synthesis of L-arabinose.
L-glukóza a L-manóza sú hexózy vzácné sacharidy, ktoré sa v prírode nenachádzajú a preto sa pripravujú synteticky. Najstaršou a najznámejšou metodou přípravy je tzv. kyanhydrinová syntéza. Aldózy poskytujú působením kyanovodíka kyanhydriny aldóz ich kyslou hydrolýzou vznikajú aldónové kyseliny, ktoré sa prevedú na laktón a v tejto formě redukujú napr. sodíkovým amalgámom za vzniku aldózy a jeden uhlíkový atóm. Tak vzniká z L-arabinózy L-glukóza a L-manóza [C. S. Hudson: Adv. Carbohydr. Chem. 1, 1 [1945); E. Fischer: Ber. 22, 2204 (1889)]. Najvhodnejšou metodou přípravy L-glukózy a L-manózy je kondenzácia L-arabinózy s nitrometanom v přítomnosti metylátu sodného. Pri tejto syntéze vzniká krystalická zmes sodných solí 1-deoxy-l-nitro-L-glucitolu a 1-deoxy-l-nitro-L-manitolu, ktoré pomocou katalyzátore kyseliny sírovej alebo peroxida vodíka sa rozkladajú za vzniku L-glukózy a L-manózy [J. C. Sowden, H. O. L. Fischer: J. Am. Chem. Soc. 67. 1963 (1947); J. C. Sowden: Methods Carbohydr. Chem. L. 132 (1962); V. Bílik: Coll. Czech. Chem. Commun. 39, 1621 (1974)]. V preparatívnom množstve sa L-glukóza a L-manóza připravuje z čistých krystalických látok 1-deoxy-l-nitro-L-glucitolu a 1-deoxy-l-nitro-L-manitolu získaných frakčnou kryštalizáciou s acetonom [J. C. Sowden, H. O. L. Fischer: J. Am, chem. Soc. 67, 1963 (1947); J. Kubala a kol.: Coll. Czech. Commun. v tlači], Alebo sa využívá priamy rozklad sodných solí, kde L-manóza sa izoluje vo formě fenylhydrazónu a po uvolnění sa katalyticky epimerizuje pomocou molybdenanových iónov na L-glukózu [Čs. AO 149463], Uvedená metoda přípravy L-glukózy a L-manózy kyanhydrinovou syntézou je značné komplikovaná pre náročnost viac stupňovej syntézy a má len teoretický význam v porovnaní so spůsobom přípravy kondenzácie s nitrometanom. Pri príprave L-glukózy, resp. L-manózy z čistých 1-deoxy-l-nitro-L-glucitolu a 1-deoxy-l-nitro-L-manitolu výstupu je obmedzujúci faktor ich vzájomnej preferenčnej kryštalizácie zo zmesi v prospěch 1-deoxy-l-nitro-L-manitolu. Pri priamom rozklade zmesi sodných solí 1-deoxy-l-nitro-L-glucitolu a 1-deoxy-l-nitro-L-manitolu izolácia L-manózy pomocou fenylhydrazínu je stažená tým, že získaná zmes vždy obsahuje vel'ké množstvo L-arabinózy, čím příprava nedosahuje uspokojivé výtažky a naviac fenylhydrazín je nebezpečný jed.L-glucose and L-mannose are hexose rare carbohydrates that are not found in nature and are therefore synthetically prepared. The oldest and best known method of preparation is so-called. cyanohydrin synthesis. Aldoses provide cyanohydrins of aldoses by the action of hydrogen cyanide to form aldonic acids by acid hydrolysis, which are converted to lactone and in this form reduced e.g. sodium amalgam to form aldose and one carbon atom. Thus, L-glucose and L-mannose arise from L-arabinose [C. S. Hudson: Adv. Carbohydr. Chem. 1, 1 [1945]; E. Fischer: Ber. 22, 2204 (1889)]. The most suitable method of preparing L-glucose and L-mannose is by condensing L-arabinose with nitromethane in the presence of sodium methylate. In this synthesis, a crystalline mixture of sodium salts of 1-deoxy-1-nitro-L-glucitol and 1-deoxy-1-nitro-L-mannitol is formed which decomposes with the aid of a sulfuric acid catalyst or hydrogen peroxide to form L-glucose and L- mannose [J. C. Sowden, H.O. L. Fischer: J. Am. Chem. Soc. 67, 1963 (1947); J. C. Sowden, Methods Carbohydr. Chem. L. 132 (1962); V. Bilik: Coll. Czech. Chem. Commun. 39, 1621 (1974)]. In preparative amounts, L-glucose and L-mannose are prepared from the pure crystalline substances 1-deoxy-1-nitro-L-glucitol and 1-deoxy-1-nitro-L-mannitol obtained by fractional crystallization with acetone [J. C. Sowden, H.O.L. Fischer: J. Am. Chem. Soc. 67, 1963 (1947); J. Kubala et al., Coll. Czech. Commun. or in the direct decomposition of sodium salts, where L-mannose is isolated in the form of phenylhydrazone and, upon release, is catalytically epimerized with molybdate ions to L-glucose [Cs. AO 149463], The method of preparing L-glucose and L-mannose by cyanohydrin synthesis is considerably complicated due to the difficulty of multi-stage synthesis and is of theoretical importance only as compared to the method of preparing condensation with nitromethane. When preparing L-glucose, resp. L-mannose from pure 1-deoxy-1-nitro-L-glucitol and 1-deoxy-1-nitro-L-mannitol output is a limiting factor of their preferential crystallization from the mixture in favor of 1-deoxy-1-nitro-L- mannitol. In the direct decomposition of a mixture of sodium salts of 1-deoxy-1-nitro-L-glucitol and 1-deoxy-1-nitro-L-mannitol, the isolation of L-mannose by phenylhydrazine is withdrawn because the mixture always contains a large amount of L- arabinose, whereby the preparation does not achieve satisfactory yields and, moreover, phenylhydrazine is a dangerous poison.
Uvedené nevýhody v podstatnej miere odstraňuje spósob přípravy L-glukózy a L-manózy podta vynálezu, ktorého podstata spočívá v tom, že sa zmes cukrov uvolněných po nitrometanovej syntéze selektívne rozdělí pomocou silné kyslého vymieňača katiónov vo vápenatej formě. Ako eluačné činidlo sa použije vodný roztok 40 až 60 % etylalkoholu. Frakcie L-glukózy a L-manózy sa zahustia na rotačnej odparke na sirup a z etylalkoholu vykryštalizujú.The above-mentioned disadvantages are substantially eliminated by the process for the preparation of L-glucose and L-mannose according to the invention, which consists in that the mixture of sugars released after nitromethane synthesis is selectively separated by means of a strong acid cation exchanger in calcium form. An aqueous solution of 40 to 60% ethyl alcohol is used as eluent. The L-glucose and L-mannose fractions are concentrated on a rotary evaporator to a syrup and crystallized from ethyl alcohol.
Výhodou navrhovaného sposobu přípravy L-glukózy a L-manózy oproti doterajším postupom přípravy je, že předmětný spůsob přípravy dovoluje vyrobit obidva sacharidy v jednom stupni. Je zdravotně nezávadný, hospodárnější, umožňuje pracovat v jednoduchých zariadeniach, ktoré sú bežne dostupné. Umožňuje pracoval bez látok, ktoré znečísťujú životné prostredie ako fenylhydrazín, ktorý ako zvlášť nebezpečný jed je karclnogénnou látkou a jeho odstránenie v prevádzkovom měřítku je nákladné, vyžaduje si speciálně zariadenie. Vyrobené produkty L-glukóza a L-manóza sa získajú vo vysokej čistotě.An advantage of the proposed method of preparing L-glucose and L-mannose over the prior art processes is that the present method of preparation allows both carbohydrates to be produced in one step. It is harmless to health, more economical, allows to work in simple devices that are commonly available. It allows to work without environmental pollutants like phenylhydrazine, which as a particularly dangerous poison is a carclogenous substance and its removal on an industrial scale is expensive, requires a special device. The products L-glucose and L-mannose are obtained in high purity.
Příklad 1Example 1
Silno kyslý vymieňač katiónov (Dowex 50 wx 8 0,07 až 0,13 mm) sa naplní do kolony dlžky 100 cm a priemeru 2,5 cm postupné sa premýva 10 % kyselinou chlorovodíkovou (1000 ml) po dobu 24 h. Ionomenič sa premyje destilovanou vodou do neutrálněj reakcie pH 7 (5000 ml). Aktivácia iontomeniča do vápenatej formy sa uskutoční 20 % roztokom chloridu vápenatého (2000 ml) a po 24 h sa nadbytočné ióny vymyjú destilovanou vodou do negatívnej reakcie na chloridy (5000 ml). Zmes cukrov 26 % L-glukózy, 71?% L-manózy a 3 % L-arabinózy (5 gj sa rozpustí v 40% etylalkohole (10 ml) a nanesie na kolonu naplnenú silno kyslým vymieňačom katiónov (Dowex 50 wx 8 0,07 až 0,13 mm vo vápenatej formě) s dížkou 100 cm a priemerom 2,5 cm. Ako eluačné činidlo sa použije 40 % etylalkohol. Pomocou zberača frakcií pri prietoku 12 ml/h sa jednotlivé frakcie sledujú papierovou chromatografiou (chromatografický papier Whatman No lj vzostupnou chromatografiou v sústave etylacetát, pyridin, voda v objemovom pomere 8:2:1a detegujú alkalickým dusičnanom strieborným, alebo za pomoci kyseliny 3,5 dinitrosalicylovej spektrofotometricky. Frakcia 1 až 42 bola negativna na cukry, frakcia 43 až 52 obsahovala L-glukózu, frakcia 53 až 56 bola negativna na cukry, frakcia 57 až 68 obsahovala L-manózu, frakcia 69 až 90 bola negativna na cukry a frakcia 91 až 93 obsahovala L-arabinózu. Frakcie, ktoré obsahovali L-glukózu a L-manózu sa jednotlivé zahustia na rotačnej odparke na sirup, prečistia prídavkom aktívneho uhlia (0,5 g) filtrujú a znovu zahustia na sirup L-glukóza (1,25 g), L-manóza (3,50 g). Prídavkom 96% etylalkoholu (20 ml) vykrystalizuje L-glukóza (1,05 g) a L-manóza (3,0 gj. Opakovanou kryštalizáciou matečných sirupov sa dosiahla výťažnosť L-glukózy 93,1 % (a)D 20 — 52° (C = 5 HgO), teplota topenia 141 až 143 °C a L-manózy 91,7 θ/0 («)D 20 —The strongly acidic cation exchanger (Dowex 50 wx 8 0.07-0.13 mm) is packed into a 100 cm long column and 2.5 cm in diameter successively washed with 10% hydrochloric acid (1000 mL) for 24 h. The ion exchanger was washed with distilled water to neutral pH 7 (5000 mL). Activation of the ion exchanger into the calcium form is carried out with a 20% calcium chloride solution (2000 ml) and after 24 h the excess ions are washed out with distilled water to a negative reaction to the chlorides (5000 ml). Mixture of 26% L-glucose, 71% L-mannose and 3% L-arabinose sugars (5 gj is dissolved in 40% ethyl alcohol (10 ml) and applied to a column packed with a strongly acid cation exchanger (Dowex 50 wx 8 0.07) up to 0.13 mm (in calcium form) with a length of 100 cm and a diameter of 2.5 cm using 40% ethyl alcohol as the eluent and using a fraction collector at a flow rate of 12 ml / h, the individual fractions are monitored by paper chromatography (Whatman No lj chromatography paper) by chromatography on a system of ethyl acetate, pyridine, water (8: 2: 1, v / v), they were detected by alkaline silver nitrate, or by means of 3,5 dinitrosalicylic acid spectrophotometrically. fraction 53-56 was negative for sugars, fraction 57-68 contained L-mannose, fraction 69-90 was negative for sugars, and fraction 91-93 contained L-arabinose. Fractions containing L-glucose and L-mannose were individually concentrated and on a rotary evaporator to a syrup, purified by addition of activated carbon (0.5 g), filtered and re-concentrated to syrup L-glucose (1.25 g), L-mannose (3.50 g). Addition of 96% ethyl alcohol (20 ml) to crystallize L-glucose (1.05 g) and L-mannose (3.0 gj. Recrystallization of the mother syrup to achieve the recovery of L-glucose 93.1% (a) H 20-52 ° (C = 5 HgO), mp 141-143 ° C and L-mannose 91.7 θ / 0 ()) D 20 -
ΒΒ
14° (C = 5 HžO), teplota topenia 130 až 132 °C.14 ° (C = 5 H 2 O), mp 130-132 ° C.
Příklad 2Example 2
Postupuje sa ako v příklade 1, s tým rozdielom, že namiesto 40 % etylalkoholu sa použije 60 % etylalkohol. Získá sa 94 % výťažnosť L-glukózy (c«)d20 — 53° (C = 5 HzO), teplota topenia 142 až 144 °C a L-manózy 92,5% («)d20 — 14,5° (C = 5 H2O), teplota topenia 131 až 132 °C.The procedure is as in Example 1, except that 60% ethyl alcohol is used instead of 40% ethyl alcohol. To give 94% yield of L-glucose (c ') d 20-53 ° (C = 5 HZO), mp 142 to 144 ° C, and L-mannose 92.5% (') d 20 to 14.5 ° ( Mp 131-132 ° C.
Vynález má rozsiahle využitie pri štúdiu biochemických pochodv, v medicíně, pri príprave nových nukleozidov v genetickom inžinierstve. L-glukóza a L-manóza patria medzi vzácné a ťažko dostupné sacharidy.The invention has extensive application in the study of biochemical processes, in medicine, in the preparation of novel nucleosides in genetic engineering. L-glucose and L-mannose are rare and hardly available carbohydrates.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS833908A CS231544B1 (en) | 1983-06-01 | 1983-06-01 | Processing of l-glucose and l-manose |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS833908A CS231544B1 (en) | 1983-06-01 | 1983-06-01 | Processing of l-glucose and l-manose |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS390883A1 CS390883A1 (en) | 1984-02-13 |
| CS231544B1 true CS231544B1 (en) | 1984-11-19 |
Family
ID=5380519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS833908A CS231544B1 (en) | 1983-06-01 | 1983-06-01 | Processing of l-glucose and l-manose |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS231544B1 (en) |
-
1983
- 1983-06-01 CS CS833908A patent/CS231544B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS390883A1 (en) | 1984-02-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3140775B2 (en) | Method for producing rhamnose from rhamnolipid | |
| US5015296A (en) | Continuous epimerization of sugars, in particular D-arabinose to D-ribose | |
| JPH11506456A (en) | Improved oxidation process | |
| MX2013003870A (en) | Method for manufacturing high-purity sorbitol syrups from sucrose and uses thereof. | |
| Bílik | Reactions of Saccharides Catalyzed by Molybdate Ions. III.* Preparation of L-Glucose by Epimerization of L-Mannose or L-Mannose Phenylhydrazone | |
| FI66830C (en) | FOERFARANDE FOER FRAMSTAELLNING AV D-MANNITOL | |
| EP0039127B1 (en) | A process for making ketose sugars | |
| JP4865128B2 (en) | High purity production of L-ribose from L-arabinose | |
| CS231544B1 (en) | Processing of l-glucose and l-manose | |
| KR910005658B1 (en) | How to separate nucleotides and nucleotides | |
| CA1242710A (en) | Crystalline maltopentaose and process for producing the same | |
| US5433793A (en) | Preparation of high purity D-allose from D-glucose | |
| US2847421A (en) | Ascorbic acid intermediates | |
| US4112221A (en) | Process for preparing 8,2'-O-anhydropurine nucleosides | |
| Hirase et al. | Constituents of the mucilage of Gloiopeltis furcata | |
| US3980719A (en) | Process for obtaining xylitol from natural products containing xylan | |
| US2779760A (en) | Lithium maltobionate and process for making same | |
| CS233220B1 (en) | Method of d-manose preparation | |
| US20040082776A1 (en) | Process for recovery of uridine from molasses | |
| JPS6337635B2 (en) | ||
| US5550227A (en) | Method for the preparation of rhamnose monohydrate from rhamnolipids | |
| CS231545B1 (en) | Processing of d-psicose | |
| CS224984B1 (en) | The production of l-talose | |
| CS227527B1 (en) | Method of preparing l-galactose | |
| UEHARA et al. | PREPARATION OF D-RIBOSE FROM D-ERYTHROSE BY CYANOHYDRIN REACTION |