CS274091B1 - 4-0-beta-d-xylopyranozyl-d-glucopyranose - Google Patents
4-0-beta-d-xylopyranozyl-d-glucopyranose Download PDFInfo
- Publication number
- CS274091B1 CS274091B1 CS491989A CS491989A CS274091B1 CS 274091 B1 CS274091 B1 CS 274091B1 CS 491989 A CS491989 A CS 491989A CS 491989 A CS491989 A CS 491989A CS 274091 B1 CS274091 B1 CS 274091B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- glucopyranose
- xylopyranozyl
- beta
- xylopyranosyl
- enzyme
- Prior art date
Links
- 102000004190 Enzymes Human genes 0.000 abstract description 5
- 108090000790 Enzymes Proteins 0.000 abstract description 5
- 244000005700 microbiome Species 0.000 abstract description 3
- 229940088598 enzyme Drugs 0.000 abstract 2
- 229940079919 digestives enzyme preparation Drugs 0.000 abstract 1
- 150000002016 disaccharides Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- -1 3-D-xylopyranosyl-O-glucopyranose Chemical compound 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- QYCFXXCSGBEENZ-RKQHYHRCSA-N [(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-3-hydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1O QYCFXXCSGBEENZ-RKQHYHRCSA-N 0.000 description 1
- AVNRQUICFRHQDY-LMLFDSFASA-N [(3r,4s,5r,6s)-4,5-diacetyloxy-6-bromooxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](Br)[C@H](OC(C)=O)[C@H]1OC(C)=O AVNRQUICFRHQDY-LMLFDSFASA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
Vynález sa týká 4-0- /í-O-xylopyranozyl-D-glukopyranózy.
Doteraz bole připravená 6-0-Á?-Q-xylopyranozyl-0-glukopyrenóza J^B.Helfarich, R. Steinpreis: Chem. Ber. 91, 1794 (1958)] · Tento diaacharid bol použitý pri Stúdiu enzymových reakclí. Nevýhodou vSak bolo,’ že nie Je vhodným aubatrátom pre mnohé enzýmy a mikroorganizmy. Doteraz 4-0-/3-D-xylopyranozyl-0-glukopyranóza nebole připravená, Túto nevýhodu odstraňuje tento vynález. Podatatou vynálezu Je 4-0-/J»D-xylopyranozyl-O-glukopyranóza vzorce
Výhodou tejto látky je, ža roziiruja možnost testovat enzýmy a mikroorganizmy. Přiklad 1
Klg 1,2,3,6-tetra-0-acetyl-/3-D-glukopyranózy aa přidá 1,5 g kyanidu ortufnatého v 10 ml ocetonltrilu a 2 g 2,3,4-tri-O-acetyl-«ί-D-xylopyranozylbromidu a za stálého mieáania ea roakčnó zmes udržuje pri teplote 20 °C počae 2 hodin. Potom ea reakčná zmea odfiltruje, zriedi 50 ml chloroformu, dvakrát vytrepe 50 ml 1 molérneho roztoku bromidu draselného, 50 ml vody, vyauči pridanim bezvodého síranu sodného, odfiltruje, zahuati. Po chromatografickom čieteni ea zíaka 1,13 g (65 %) l,2,3,6-tetro-0-ecetyl-4-0-(2,3,4-tri0-acetyl-/í-D-xylopyranozyl)-/í-O-flukopyranózy, po rakryčtalizácii z etanolu a teplotou topenia 160 až 161 °C,’ Specifickou otáčavoafouToí]25 - 38,6 0 (e 0/86,1 chloroform). 0 ·
Elementárna analýza pre ^gHggOj?, mol. hmotnost 806,52i vypočítané: 49,50 hmot. % uhlíka,' 5,82 hmot, % vodíka, zlatěné : 49,51 hmot. % uhlíka, 5,72 hmot. % vodika.
Acetylové skupiny aa odstránia pSeobenim 1 molérneho matanolétu sodného. Produkt aa po ketlonizácli na katexe a funkčnými eulfoakupinami (Domex 80 W X 4 0,040 až 0,075 mm) kryéta llzoval z metanolu,· teplota topenia po rakryitallzácii bola 218 až 220 °C, Specifická otáčavoet ♦ 24,5 0 (c 0,97, voda).
Elementárna analýza pre θχχΗ20°10* B0^· hmotnost 312,27« vypočítané i 42,'31 hmot. % uhlika, 6,45 hmot. % vodika. zlatěné; 42,10 hmot. % uhlika, 6,53 hmot. % vodíka* 4-0-^-D-Xylopyranožyl-D-glukopýřanóza može néjat áiroké použitie v enzýmovaj, organickej chémii a na rozliěenle raikroorganizmov.
The present invention relates to 4-O-N-O-xylopyranosyl-D-glucopyranose.
6-0-β-β-xylopyranosyl-O-glucopyrenose prepared by JH B. Helfarich, R. Steinpreis: Chem. Ber. 91, 1794 (1958)] · This diaacharide was used in the Study of Enzyme Reactions. The disadvantage, however, is that it is not a suitable aubatrate for many enzymes and microorganisms. So far, 4-O- (3-D-xylopyranosyl-O-glucopyranose) has not been prepared. DETAILED DESCRIPTION OF THE INVENTION There is a 4-O- (D-xylopyranosyl-O-glucopyranose) formula
The advantage of this substance is that it extends the ability to test enzymes and microorganisms. Example 1
Klg of 1,2,3,6-tetra-O-acetyl-β-D-glucopyranose and add 1.5 g of orthophosphate cyanide in 10 ml of ocetonltril and 2 g of 2,3,4-tri-O-acetyl-β -D-xylopyranosyl bromide and maintained at 20 [deg.] C. with stirring for 2 hours. Then, the reaction mixture is filtered off, diluted with 50 ml of chloroform, shaken twice with 50 ml of 1 molar potassium bromide solution, 50 ml of water, extracted with anhydrous sodium sulfate, filtered and concentrated. After chromatographic purification, 1.13 g (65%) of 1,2,3,6-tetro-O-ethyl-4-O- (2,3,4-tri-acetyl- [beta] -D-xylopyranosyl) is obtained. [beta] -O-flucopyranose, after racialization from ethanol and m.p. 160-161 [deg.] C., " Specific Rotation " 0 ·
Elemental analysis for? GHgO3 ?, mol. mass 806.52i calculated: 49.50 wt. % carbon, '5.82 wt.% hydrogen, gold: 49.51 wt. % carbon, 5.72 wt. % vodika.
The acetyl groups and aa are removed by treatment with 1 molar sodium methanolate. The product a, after ketlonation on cation exchanger and functional sulfonates (Domex 80 WX 4 0.040-0.075 mm), was lysed from methanol, the melting point was 218-220 ° C, the specific rotation was 24.5 ° (c 0.97, water ).
Elemental analysis for CH 2 O 2 O 10 · B 2 O · Mass 312.27 Calcd. % carbon, 6.45 wt. % vodika. golden; 42.10 wt. % carbon, 6.53 wt. % hydrogen of 4-O-D-Xylopyranosyl-D-glucopyranoside may not be widely used in enzyme, organic chemistry, and microbial diversity.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS491989A CS274091B1 (en) | 1989-08-22 | 1989-08-22 | 4-0-beta-d-xylopyranozyl-d-glucopyranose |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS491989A CS274091B1 (en) | 1989-08-22 | 1989-08-22 | 4-0-beta-d-xylopyranozyl-d-glucopyranose |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS491989A1 CS491989A1 (en) | 1990-08-14 |
| CS274091B1 true CS274091B1 (en) | 1991-04-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS491989A CS274091B1 (en) | 1989-08-22 | 1989-08-22 | 4-0-beta-d-xylopyranozyl-d-glucopyranose |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS274091B1 (en) |
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1989
- 1989-08-22 CS CS491989A patent/CS274091B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS491989A1 (en) | 1990-08-14 |
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