CS224985B1 - The production of l-talose - Google Patents
The production of l-talose Download PDFInfo
- Publication number
- CS224985B1 CS224985B1 CS599782A CS599782A CS224985B1 CS 224985 B1 CS224985 B1 CS 224985B1 CS 599782 A CS599782 A CS 599782A CS 599782 A CS599782 A CS 599782A CS 224985 B1 CS224985 B1 CS 224985B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- talose
- toluidine
- galactose
- tolyl
- talozylamine
- Prior art date
Links
- GZCGUPFRVQAUEE-OMMKOOBNSA-N aldehydo-L-talose Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-OMMKOOBNSA-N 0.000 title 1
- GZCGUPFRVQAUEE-KAZBKCHUSA-N aldehydo-D-talose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)C=O GZCGUPFRVQAUEE-KAZBKCHUSA-N 0.000 claims description 15
- 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 12
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- GZCGUPFRVQAUEE-UHFFFAOYSA-N 2,3,4,5,6-pentahydroxyhexanal Chemical compound OCC(O)C(O)C(O)C(O)C=O GZCGUPFRVQAUEE-UHFFFAOYSA-N 0.000 description 1
- YVECGMZCTULTIS-HSUXUTPPSA-N D-galactal Chemical compound OC[C@H]1OC=C[C@@H](O)[C@H]1O YVECGMZCTULTIS-HSUXUTPPSA-N 0.000 description 1
- LLPWGHLVUPBSLP-IJLUTSLNSA-N [(2r,3r,4r)-3,4-diacetyloxy-3,4-dihydro-2h-pyran-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1OC=C[C@@H](OC(C)=O)[C@H]1OC(C)=O LLPWGHLVUPBSLP-IJLUTSLNSA-N 0.000 description 1
- CYAYKKUWALRRPA-RRYROLNDSA-N [(2r,3s,4s,5r)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1OC(Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O CYAYKKUWALRRPA-RRYROLNDSA-N 0.000 description 1
- 230000003851 biochemical process Effects 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- -1 molybdenum ions Chemical class 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Description
Vynález sa týká sposobu přípravy D-talózy zo zmesi cukrov D-talóza D-galaktóza.The present invention relates to a process for the preparation of D-talose from a mixture of sugars D-talose D-galactose.
D-talóza patří medzi vzácné sacharidy, aldohexózy, ktoré sú velmi ťažko dostupné. Připravuje sa z D-galaktózy viacstupňovou syntézou cez tetra-O-acetyl-D-galaktozylbromid, tri-O-acetyl-D-galaktál a D-galaktál /f. Shafizadeh: Methods Carbohyd.Chem. 2,409 /1963// , jfR.S.Tipson, H.S.Isbell: Methods Carbohyd.Chem, 1, 157 /1962// , alebo epimerizáciou za katalytického účinku molybdénanových iónov /v. Bílik:D-talose is a rare carbohydrate, aldohexose, which is very difficult to access. It is prepared from D-galactose by multistep synthesis via tetra-O-acetyl-D-galactosyl bromide, tri-O-acetyl-D-galactal and D-galactal / f. Shafizadeh: Methods Carbohyd. 2,409 (1963), J. T. Tipson, H. S.sbell: Methods Carbohyd.Chem, 1, 157 (1962), or by epimerization under the catalytic action of molybdenum ions (v. Bílik:
Coli,Czech.Chem,Commun. -^9,1621 /1974// , V uvedených prípadoch je získaná D-talóza znečistěná D-galaktózou, ktorá sa dá len ťažko a nedokonale odstranit’ frakčnou kryštalizáciou alebo skvasením.Coli Czech.Chem, Commun. In these cases, the D-talose obtained is contaminated with D-galactose, which is difficult to remove imperfectly by fractional crystallization or fermentation.
Uvedené nevýhody v podstatnej miere odstraňuje spósob přípravy D-talózy podlá vynálezu, ktorého podstata spočívá v tom, že sa zo zmesi D-talózy a D-galaktózy pomocou p-toluidínu izoluje kryštalický N-p-tolyl-D-talozylamin, ktorý sa * rozloží hydrolýzou za súčasného oddestilovania p-toluidínu vodnou parou a vykryštalizuje sa z metanolu.The above-mentioned disadvantages are substantially eliminated by the process for the preparation of D-talose according to the invention, characterized in that crystalline Np-tolyl-D-talozylamine is isolated from the mixture of D-talose and D-galactose by p-toluidine, which is decomposed by hydrolysis. while p-toluidine was distilled off with water vapor and crystallized from methanol.
Příklad 1Example 1
Příprava N-p-tolyl-D-talozylaminu. K roztoku, ktorý obsahuje D-talózu /8,0 g/ a D-galaktózu /2,0 g/ v /25 ml/ vody sa přidá roztok p-toluidínu /6,0 g/ v 96 $ etanole /25 ml/ a /0,5 ml/ 10 % kyseliny octovej. Vykryštalizuje Np-tolyl-D-talozylamin, ktorý sa odfiltruje a premyje 50 % etanolóm /150 ml/, Zís^a sa 11,0 až 11,5 g N-p-tolyl-D-talozyamínu, čo zodpovedá 7,4 až 7,7 g volnej D-talózy. Teplota topenia 124°C.Preparation of N-p-tolyl-D-talozylamine. To a solution containing D-talose (8.0 g) and D-galactose (2.0 g) in (25 ml) water was added a solution of p-toluidine (6.0 g) in 96% ethanol (25 ml). and (0.5 ml) 10% acetic acid. Np-tolyl-D-talozylamine crystallizes out and is filtered off and washed with 50% ethanol (150 ml) to give 11.0 to 11.5 g of Np-tolyl-D-talozyamine corresponding to 7.4 to 7, 7 g of free D-talose. Melting point 124 ° C.
J!J!
224 985 fríprava kryštalickej D-talózy. N-p-tolyl-D-talozylamin /7»5 g/ sa suspenduje v /200 ml/ vody a zmes sa podrobí destilaci! s vodnou parou, aby sa odstranil p-toluidín. Získaný roztok D-talózy sa odfarbí aktívnym uhlím /15 g/ a zahustí na sirup, ktorý sa rozpustí /40 ml/ metanolu, Vykrystalizuje 7,o g . D-talózy chrornatcgraficky čistej. + 20,6°,· Teplota topenia 151°C, v 87,5 A výtažku z množstva D-talózy prítomnej v povodnej zmesi cufcrov.224 985 crystalline D-talose fraction. N-p-tolyl-D-talozylamine (7.5 g) was suspended in (200 ml) water and the mixture was distilled! with water vapor to remove p-toluidine. The D-talose solution obtained is decolourised with activated charcoal (15 g) and concentrated to a syrup which is dissolved (40 ml) of methanol. D-talose in chromatoscopically pure. + 20.6 °, m.p. 151 ° C, in 87.5 A extract from the amount of D-talose present in the float mixture.
Vynález má rozsiahle použitie pri studiu biochemických a biologických pochodov a v medicíně. D-talóza patří medzi vzácné a ťažko dostupné sacharidy.The invention has extensive application in the study of biochemical and biological processes and in medicine. D-talose is a rare and hardly available carbohydrate.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS599782A CS224985B1 (en) | 1982-08-13 | 1982-08-13 | The production of l-talose |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS599782A CS224985B1 (en) | 1982-08-13 | 1982-08-13 | The production of l-talose |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS224985B1 true CS224985B1 (en) | 1984-02-13 |
Family
ID=5406036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS599782A CS224985B1 (en) | 1982-08-13 | 1982-08-13 | The production of l-talose |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS224985B1 (en) |
-
1982
- 1982-08-13 CS CS599782A patent/CS224985B1/en unknown
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 | |
| EP0914312B1 (en) | Method for producing xylitol | |
| Anderson et al. | Stereochemical Studies in the Aminodesoxyinositol Series. meso-Inosamine-2 and scyllo-Inosamine1 | |
| JPS62126193A (en) | Method for producing L-rhamnose | |
| Smith | 588. The constitution of mesquite gum. Part III. The structure of the monomethyl glucuronic acid component | |
| FI66830B (en) | FOERFARANDE FOER FRAMSTAELLNING AV D-MANNITOL | |
| TWI295294B (en) | Process for producing high 2-o-α-d-glucopyranosyl-l-ascorbic acid content product | |
| CS224985B1 (en) | The production of l-talose | |
| Jones et al. | Synthesis of sugars from smaller fragments: part XII. Synthesis of D-glycero-D-altro-, L-glycero-L-galacto-, D-glycero-L-gluco-, and D-glycero-L-galacto-octulose | |
| Frush et al. | Sugars: Preparation of D-Arabinose-5-C14 From D-Fructose-1, 6-C14 (1, 2) | |
| Sephton et al. | The Isolation of a Second Octulose and of a Heptose from the Avocado: D-glycero-L-galacto-Octulose and D-glycero-D-galacto-Heptose1 | |
| JPS6327496A (en) | Production of l-fucose | |
| DE3437571A1 (en) | METHOD FOR PRODUCING A D-RIBOSE-CONTAINING SOLUTION | |
| JPS6147495A (en) | Maltopentaose crystal and its preparation | |
| Irvine et al. | XXVII.—The action of ammonia and alkylamines on reducing sugars | |
| Schaffer | The isomerization of d-manno-3-heptulose by alkali | |
| Hall et al. | Formation of arabinose, ribulose and tartronic acid from 2-keto-d-gluconic acid | |
| US20040082776A1 (en) | Process for recovery of uridine from molasses | |
| Ingold | CCCXXII.—The conditions underlying the formation of unsaturated and cyclic compounds from halogenated open-chain derivatives. Part V. Products derived from α-halogenated β-methylglutaric acids | |
| Hough et al. | 244. The synthesis of sugars from simpler substances. Part I. The in vitro synthesis of the pentoses | |
| Woods et al. | PREPARATION OF SOME NEW BRANCHED-CHAIN CARBOHYDRATES FROM d-α-FRUCTOHEPTONIC LACTONE | |
| FI59241C (en) | CRYSTALIZATION OF XYLITOL IN VAT | |
| Pravdić et al. | Allylic Displacement Reactions of a 2-Acetamido-D-glucal Derivative with Acids and Phenols | |
| Ballou et al. | The Preparation and Alkali Sensitivity of Some New Enol Glucosides and Glucosides of β-Hydroxy Carbonyl Compounds1 |