CS271975B1 - é-Metylumbelliferyl-2,3-di-O-acetyl-/3- -D-xylopyranozid a sposob jaho pripravy - Google Patents
é-Metylumbelliferyl-2,3-di-O-acetyl-/3- -D-xylopyranozid a sposob jaho pripravy Download PDFInfo
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- CS271975B1 CS271975B1 CS887599A CS759988A CS271975B1 CS 271975 B1 CS271975 B1 CS 271975B1 CS 887599 A CS887599 A CS 887599A CS 759988 A CS759988 A CS 759988A CS 271975 B1 CS271975 B1 CS 271975B1
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- xylopyranoside
- methylumbelliferyl
- acetyl
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- tri
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Abstract
Rlešenle ea týká novej zlúčeniny a spSsobu pripravy 4-metylumbelliferyl-4- -D-2,3-di-O-acetyl-xylopyranozidu. Uvedeného účelu ea dosiahne tým, že na 4-metylumbellifery1-2,3,4-tri-O-acetyl- -d-D-xylopyranozid v prostredi pyridinu sa porobi hydrazinhydrátom po dobu 2 hodin při teplote 20 až 25 t>C a zo vznlknutej reakčnej zmesi sa chromatografickou saparáciou zleka 4-matylurabelliferyl-2,3- -di-O-acetyl-d-D-xylopyranozid. Riešenie má použitie jednak v základnom chemickom a biologickora výskume sacharidov, jednak pri priprava komerčně zaujimavých 4-metylumbelliferyl-A-glykozidov oligosacharidov, potenciálnycn fluoroganných eubetrátov pre niektoré endo-4-l,4-xylanázy a yj-xylozidázy.
Description
Vynález sa týká 4-metylumbellifsryl-2,3-di-O-acstyl-ó-O-xylopyranozidu a sposobu jeho pripravy. 4-Matylumbellifaryl-/?-D-xylopyranozid (UMB-j-D-xylopyranozid) prip. jeho deriváty možu nájat uplatnenia v biochémii sacharidov ako fluoroganné eubetráty pra ó-xylozidázy (EC 3,2.1.37). 4-Metylumbsllifaryl-2,3-di-O-acetyl-rf-D-xylopyranozid Je vhodným prskurzorom pri priprava 4-metylumbellifaryl-£-glykozidov oligoaacharldov, potanciálnych eubstrátov pra niektoré typy ando-Λ-Ι,4-xylanáz (EC 3,2.1,8) a 4_D“Xyl°zidáz xylobiózového a exo-xylanázového typu. Analogická deriváty glukózy, calobiózy a laktózy aa využívajú na datekciu a difaranciáciu calulolytických enzýmov /Van Tilbeurgh H., Claeyesens M., Oe Bruyna C.K. FEBS Letters 149, 152 (1982), Van Tilbeurgh H., Clayaseane M., FEBS Lattara 178 283 (1985), Bialy P., Markovič O., Biotachnol. Appl. Biochem. JO, 99 (1988)/. 4-Metylumbellifaryl-2,3-di-O-acetyl-yJ-D-xylopyrazonid, ktorý nebol doteraz v literatúre popiaaný ja predmetom tohto vynálezu. Podstata vynálezu spočiva tiež v posoboni hydrazin hydrátu pri teplota 20 až 25 °C na 4-matylumballifaryl-2,3,4-tri-0-acetyl-Á-D-xylopyranozid v proatradi pyridinu po dobu 2 hodin, Výťažok 4-metylumbelliferyl-2,3-di-O-acetyl-4-D-xylopyranozidu v tajto reakcii Ja cca 23 %, Z vedlajSich produktov, okrem 9alšich di-O-acatyl derivátov 4-matylumbellifaryl-/|-D-xylopyranozidu, převláda východzi 4-metylumbelliferyl-2,3,4-tri-0-acetyl-/f-D-xylopyranozidu v cca 40 % zaetúpeni, ktorý po separácii možno použit na clalšiu hydrazlnolyzu. výhodou tohto postupu ja jednoduchost prevedenia a možnost pripravy 4-metylumbelliferyl-2,3-di-O-acetyl-4-D-xylopyrenozidu v jednom reakčnom stupni. Přiklad 1 2,17 g 4-metylumbelliferyl-2,3,4-tri-0-acetyl-y?-D-xylopyranozidu ea rozpustí v 50 ml pyridinu a do roztoku sa přidá 1 ml hydrazin hydrátu, výsledný reakčný roztok se drži pri teplote 20 - 25 °C po dobu 2 hodin. Potom sa k němu přidá 50 ml acetonu a po 2 hodinovom mieéani sa zahusti do sirupu. Separácia 4-metylumbelllferyl-2,3-diacetyl-yí-D-xylopyranozidu z reakčnej zmesi sa uekutočni chromatografiou na koloně 8 nóplňou eilikagélu v chromatograflekej súetave octan etylovy : benzén : hexán (5:2:2 objemových podielov). Ziska aa 0,45 g (23 %) chromatografický čistého 4-metylumbellif eryl-2,3-di-0-ecetyWJ-D-xylopyranozidu o t.t, 108 až 110 °C a/oc/θ° -14,5° (CHClg).
Vynález može nájat uplatnenie pri syntéze komerčně zaujimavych 4-metylumbelliferyl-4-glykozidov oligosacharidov, potanciálnych fluoroganných subetrátov pre niektoré endo-/J-l,4-xylenázy a #-xylozidézy.
Claims (2)
- PREDMET VYNÁLEZU 1· 4-Metylumbelllferyl-2,3-di-O-acetyl-/J-D-xylopyranozid.
- 2. Sposob pripravy 4-metylumballifaryl-2,3-di-O-acatyl-/í-D-xylopyranozidu podía bodu 1 vyznačeny tym, že sa poeobi na 4-metylumbelliferyl-2,3,4-tri-O-acetyl-/5-D-xylopyra- nozid hydrazin hydrátom v proetredi pyridinu po dobu 2 hod. pri teplote 20 až 25 °C a po chromatograflekej separácii sa získá čisty produkt.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS887599A CS271975B1 (cs) | 1988-11-21 | 1988-11-21 | é-Metylumbelliferyl-2,3-di-O-acetyl-/3- -D-xylopyranozid a sposob jaho pripravy |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS887599A CS271975B1 (cs) | 1988-11-21 | 1988-11-21 | é-Metylumbelliferyl-2,3-di-O-acetyl-/3- -D-xylopyranozid a sposob jaho pripravy |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS759988A1 CS759988A1 (en) | 1990-03-14 |
| CS271975B1 true CS271975B1 (cs) | 1990-12-13 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS887599A CS271975B1 (cs) | 1988-11-21 | 1988-11-21 | é-Metylumbelliferyl-2,3-di-O-acetyl-/3- -D-xylopyranozid a sposob jaho pripravy |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS271975B1 (cs) |
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1988
- 1988-11-21 CS CS887599A patent/CS271975B1/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS759988A1 (en) | 1990-03-14 |
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