CS221039B1 - Method of preparation of the d-tagatose - Google Patents
Method of preparation of the d-tagatose Download PDFInfo
- Publication number
- CS221039B1 CS221039B1 CS93282A CS93282A CS221039B1 CS 221039 B1 CS221039 B1 CS 221039B1 CS 93282 A CS93282 A CS 93282A CS 93282 A CS93282 A CS 93282A CS 221039 B1 CS221039 B1 CS 221039B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- tagatose
- galactose
- preparation
- exchange resin
- pyridine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 6
- BJHIKXHVCXFQLS-PQLUHFTBSA-N keto-D-tagatose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-PQLUHFTBSA-N 0.000 title 1
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 claims description 22
- LKDRXBCSQODPBY-OEXCPVAWSA-N D-tagatose Chemical compound OCC1(O)OC[C@@H](O)[C@H](O)[C@@H]1O LKDRXBCSQODPBY-OEXCPVAWSA-N 0.000 claims description 12
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000003957 anion exchange resin Substances 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 238000010956 selective crystallization Methods 0.000 claims description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 239000003729 cation exchange resin Substances 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-KAZBKCHUSA-N D-altritol Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KAZBKCHUSA-N 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 241000589232 Gluconobacter oxydans Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Vynález sa týká spůsobu výroby D-tagatózy z D-galaktózy.The invention relates to a process for the production of D-tagatose from D-galactose.
Na přípravu D-tagatózy sa využívá C. A. Lobry De Bruyn and W. Alberda Van Ekensteinova izomerizácia [Rec. Trav. Chim, 14, 195 (1895); 16, 257, 262, 274 (1897)], ktorý ako prvý připravil D-tagatózu z D-galaktózy za použitia pyridinu. Túto reakciu modifikoval T. Reichstein, W. Bosshard [Hevl. Chem. Acta 17, 753 (1934)], kde ako izomerizačné činidlo použil zmes pyridinu a oxidu vápenatého a nezreagovanú D-galaktózu odstránil fermentáciou za použitia kultúry Saccharomyces cerevisiae Y-30. D-tagatóza bola získaná v 6 % výtažku. Vo výtažku až 80 °/o 'bola D-tagatóza připravená oxidáciou D-talito'lu kultúrou Acetobacter suboxydans [E. L. Totton, H. A. Lardy J.: Am. Chem. Soc. 71, 3076 (1949)]. Příprava D-tagatózy pomocou pyridinu alebo pyridinu a oxidu vápenatého, resp. oxidáciou talitolu je v preparatívnom měřítku ťažko realizovatelná, pretože práca s pyridínom za tepla je zdraviu nebezpečná. Příprava D-tagatózy oxidáciou D-talitolu je ekonomicky nevýhodná, pretože východisková surovina je drahšia ako konečný produkt.C.A. Lobry De Bruyn and W. Alberda Van Ekenstein's isomerization [Rec. Trav. Chim, 14,195 (1895); 16, 257, 262, 274 (1897)], which first prepared D-tagatose from D-galactose using pyridine. This reaction was modified by T. Reichstein, W. Bosshard [Hevl. Chem. Acta 17, 753 (1934)], wherein it used a mixture of pyridine and calcium oxide as isomerizing agent and removed unreacted D-galactose by fermentation using a culture of Saccharomyces cerevisiae Y-30. D-tagatose was obtained in 6% yield. In a yield of up to 80% D-tagatose was prepared by oxidation of the D-talito by a culture of Acetobacter suboxydans [E. L. Totton, H.A. Lardy J .: Am. Chem. Soc. 71, 3076 (1949)]. Preparation of D-tagatose using pyridine or pyridine and calcium oxide, respectively. Oxidation of talitol is difficult to carry out on a preparative scale because working with pyridine while hot is dangerous to health. The preparation of D-tagatose by oxidation of D-talitol is economically disadvantageous since the starting material is more expensive than the end product.
Uvedené nevýhody v podstatnej miere odstraňuje spósob přípravy D-tagatózy podfa vynálezu, ktorého podstata spočívá v tom, že sa D-galakitóza izomerizuje vo vodnom iprostredí za katalytického účinku ionomeniča silné bázického anexu v OH- formě pri teplote 30 až 90 °C po dobu 4 až 12 hodin. Zo vzniknutej reakčnej zmesi D-galaktózy a D-tagatózy sa časť D-galaktózy od dělí selektívnou kryštalizáciou a D-tagaitóza sa získá chromatografiou na sline kyslom katexe, ktorý je vo vápenatej formě.The above-mentioned disadvantages are substantially eliminated by the process for the preparation of D-tagatose according to the invention, which is characterized in that D-galakitosis isomerized in an aqueous environment under the catalytic action of a strong basic anion exchange resin in OH - form at a temperature of 30 to 90 ° C. up to 12 hours. From the resulting reaction mixture of D-galactose and D-tagatose, a portion of D-galactose is separated from the crystallization by selective crystallization and D-tagaitose is obtained by salification with a cationic acid which is in calcium form.
Výhodou navrhovaného spósobu přípravy D-tagatózy oproti doterajším postupom přípravy je, že předmětný spósob je jednoduchší, ekonomicky nenáročný a zdravotně nezávadný.The advantage of the proposed process for the preparation of D-tagatosis over the prior art processes is that the process is simpler, economically undemanding and harmless to health.
PřikladlEXAMPLE
Zmes 500 g D-galaktózy sa rozpustí v 5 1 vody a přidá sa 0,5 kg ionomeniča v OH“ formě a mieša pri 60 °C po dobu 6 hodin. Roztok sa od ionomeniča oddělí filtráciou a přečistí prídavkom 100 g aktívneho uhlia, filtruje a filtrát zahustí na sirup, ktorý sa znova rozpustí prídavkom 500 ml metanolu a nechá sa pri teplote 10 °C krystalizovat. Kryštalický podiel D-gaiaktózy sa odfiltruje, zahustí a kryštalizácia sa opakuje. Dvojnásobnou kryštalizáciou sa získá 300 g D-gálaktózy v 60 % výtažku. Filtrát sa zahustí na 80% sirup, rozpustí v 360 ml 50 % etanolu a chromatografuje na silné kyslom ionomeniči vo vápenatej formě. Ako elučné činidlo sa použije 50 % etanol. Reakčná zmes sa frakcionuje na kolóne silné kyslého ionomeniča vo vápenatej formě s dížkou 100 cm a priemerom 8 cm pri prietoku 1 ml/ /min elučného činidla 50 % etanolu, čím sa získá 103 g kryštalickej D-tagatózy o t. t. 124CC, [«]D 20 —4,8 (c = 5 vo vodě] v 20,6 % výtažku.A mixture of 500 g of D-galactose is dissolved in 5 l of water and 0.5 kg of ion exchanger in OH form is added and stirred at 60 ° C for 6 hours. The solution is separated from the ion exchanger by filtration and purified by the addition of 100 g of activated carbon, filtered and the filtrate is concentrated to a syrup which is redissolved by the addition of 500 ml of methanol and left to crystallize at 10 ° C. The crystalline portion of D-galactose is filtered off, concentrated and the crystallization is repeated. Two crystallizations yielded 300 g of D-galactose in 60% yield. The filtrate is concentrated to 80% syrup, dissolved in 360 ml of 50% ethanol and chromatographed on a strong acid ion exchanger in calcium form. 50% ethanol was used as eluent. The reaction mixture was fractionated on a strong calcium ion exchanger column in calcium form having a length of 100 cm and a diameter of 8 cm at a flow rate of 1 ml / min of 50% ethanol eluent to give 103 g of crystalline D-tagatose of mp 124 ° C. D 20 - 4.8 (c = 5 in water) in 20.6% yield.
D-tagatóza patří medzi vzácné keto-cukry a može nájsť široké použitie pri štúdiu biochemických iprocesov a v medicíně.D-tagatosis is a rare keto-sugar and can be widely used in the study of biochemical iprocesses and in medicine.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS93282A CS221039B1 (en) | 1982-02-11 | 1982-02-11 | Method of preparation of the d-tagatose |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS93282A CS221039B1 (en) | 1982-02-11 | 1982-02-11 | Method of preparation of the d-tagatose |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS221039B1 true CS221039B1 (en) | 1983-04-29 |
Family
ID=5342436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS93282A CS221039B1 (en) | 1982-02-11 | 1982-02-11 | Method of preparation of the d-tagatose |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS221039B1 (en) |
-
1982
- 1982-02-11 CS CS93282A patent/CS221039B1/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4521252A (en) | Process for producing a high-purity isomaltose | |
| AU594316B2 (en) | Process for the preparation of crystalline maltitol | |
| EP0554090B1 (en) | Process for preparing high alpha-glycosyl-L-ascorbic acid | |
| US3755294A (en) | Process for the production of d-arabinose | |
| FI66830B (en) | FOERFARANDE FOER FRAMSTAELLNING AV D-MANNITOL | |
| Bílik | Reactions of Saccharides Catalyzed by Molybdate Ions. III.* Preparation of L-Glucose by Epimerization of L-Mannose or L-Mannose Phenylhydrazone | |
| EP0021231A2 (en) | Process for the preparation of 5'-deoxy-5-fluoro uridine and intermediates in this process | |
| JPH0569116B2 (en) | ||
| EP0075262B1 (en) | Process for the preparation of 5-ribo nucleotides | |
| KR100508724B1 (en) | How to prepare trehalose and sugar alcohol | |
| JPH0631285B2 (en) | Method for producing high-purity oligoglucosylfructoside | |
| CS221039B1 (en) | Method of preparation of the d-tagatose | |
| CA1083988A (en) | High mannitol process (enzymatic isomerization) | |
| KR19980080086A (en) | Method for producing D-glucuronolactone | |
| JPS60239496A (en) | Preparation of n6-substituted-adenosine-3',5'-cyclic phosphate and salt thereof | |
| JP3643603B2 (en) | Process for producing purified fructooligosaccharides | |
| US5856469A (en) | Method for producing palatinitol | |
| JP2787689B2 (en) | Isomaltose-rich powder and method for producing the same | |
| Stevens et al. | Synthesis and reactions of azido halo sugars | |
| CN111909224B (en) | Method for separating and purifying trehalose from mixture containing trehalose and maltose | |
| JPH0584090A (en) | Production of high-purity isomaltose | |
| JPS6216497A (en) | Purification of cytidine-5'-diphosphate choline | |
| SK69795A3 (en) | Method of producing alpha, alpha-trehaloze | |
| CS221038B1 (en) | A method of preparing D-sorbose | |
| CS239597B1 (en) | Preparation method of melibiose and d-fructose |