CS201336B1 - Method of preparing d-erythrose /u up 14c/ from radioactive polysaccharide /u up 14c/ and their p-nitro-phenyl-hydrazone - Google Patents

Method of preparing d-erythrose /u up 14c/ from radioactive polysaccharide /u up 14c/ and their p-nitro-phenyl-hydrazone Download PDF

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CS201336B1
CS201336B1 CS600578A CS600578A CS201336B1 CS 201336 B1 CS201336 B1 CS 201336B1 CS 600578 A CS600578 A CS 600578A CS 600578 A CS600578 A CS 600578A CS 201336 B1 CS201336 B1 CS 201336B1
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erythrose
water
solution
dissolved
allowed
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CS600578A
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Czech (cs)
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Stefan Kucar
Juraj Zemek
Kazimir Linek
Jozef Kolina
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Stefan Kucar
Juraj Zemek
Kazimir Linek
Jozef Kolina
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Priority to CS600578A priority Critical patent/CS201336B1/en
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201 336 0« (Bl) ČESKOSLOVENSKASOCIALISTICKÁREPUBLIKA( 19 )201 336 0 «(Bl) CZECHOSLOVAKCASOCIALISTREPUBLIC (19)

ÚŘAD PRO VYNÁLEZYOFFICE OFFICE

A OBJEVYAND DISCOVERY

POPIS VYNÁLEZUDESCRIPTION OF THE INVENTION

K AUTORSKÉMU OSVEDČENIU (61) (23) Výstavná priorita(22) Přihlášené 18 09 78 (21) FV 6005-78 (40) Zverejnené 29 02 80(45) Vydané 01 03 83 (51) Int. Cl? C 07 H 3/02TO THE CERTIFICATE OF CERTIFICATE (61) (23) Exhibition priority (22) Enrolled 18 09 78 (21) FV 6005-78 (40) Published 29 02 80 (45) Published 01 03 83 (51) Int. Cl? OJ C 07 H 3/02

Autor vynálezu KUČÁR ŠTEFAN RNDr. CSc., BRATISLAVA, ZEMEK JURAJ ing. CSc., LBTONICA,LINEK KAZIMÍR ing. CSc., BRATISLAVA a KOLÍNA JOZEF ing. CSc., PRAHAAuthor of the invention KUČÁR ŠTEFAN RNDr. CSc., LBTONICA, LINK KAZIMÍR ing. CSc., BRATISLAVA and KOLÍN JOZEF ing. CSc., PRAGUE

SpSsob přípravy D-erytrózy /U-14C/ z rádioaktívneho polysacharidu /U-* 1^/ a jejp-nitro-fenylhydrazónu 1Process for the preparation of D-erythrose (U-14C) from the radioactive polysaccharide (U- * 1) and its p-nitro-phenylhydrazone 1

Vynález sa týká spósobu přípravy D-erytrózy /U-^C/ z rádioaktívneho polysacharidua 0ej p-nitro-fenylhydrazónu.The invention relates to a process for the preparation of D-erythrose (U-C) from the radioactive polysaccharide and p-nitro-phenylhydrazone.

Vodorozpustný rédioaktivny polysecharid typu oC /1 —* 4/ glukénu větveného oC/1—'6/vazbami získaný v procese komplexného sprscovania radioaktivněj biomasy zelených alebomodrozelených rias kultivovaných v prostředí ^^C02 /Cel. patent 121 808/ je vhodnou su-rovinou na přípravu vzácných cukrov.The water-soluble oC / 1 44 / glucan-type polycyclic polysecharide branched by bamiC / 66 / bonds obtained in the process of complex scoring of the radioactive biomass of green or non-biodegraded algae cultured in the ^^C02 / Cel medium. Patent 121,808 / is a suitable substrate for the preparation of rare sugars.

Podstata vynálezu spočívá v přípravě D-erytrózy /U-^^C/ resp. jej p-N02-fenylhydra-zónu z rádioaktívneho biologického materiálu a výhodou zo zelených, resp. modrozelenýchrias tak, že hydrolyzát získaný z vodorozpustného polysacharidu /U-^^C/ typu oc /1 —— 4/glukánu účinkom minerálnych kyselin alebo enzýmu glukoamylázy sa podrobí oxidatívnemuodbúraniu octanom olovičitým. D-erytróza /U-^C/ sa izoluje z reakčného prostredia vovýtažku cca 50 % a pósobením p-nitrofenylhydrazínu sa prevedie na stabilný p-nitrofenyl-hydrazon D-erytrózy /U-^^C/. Výhodou navrhovaného spósobu přípravy D-erytrózy /U-^^C/ je jeho jednoduchost, nízképracovné náklady a možnost prechovávania D-erytrózy /U-^C/ vo formě jej stabilného hy-drazónu. D-erytróza /U-^^C/ je dóležitá látka pri biochemickom výskume a pri štúdiuchémie sacharidov. 201 336SUMMARY OF THE INVENTION The present invention is based on the preparation of D-erythrose (U -? - C) and the? its p-NO 2 -phenylhydrazone from the radioactive biological material, and preferably from green, respectively. the blue-green so that the hydrolyzate obtained from the water-soluble polysaccharide (U -? - C) of the type? 1/4 / glucan by the action of mineral acids or the enzyme glucoamylase is subjected to lead acetate oxidation degradation. D-erythrose (U-C) is recovered from the reaction medium at a rate of about 50% and is converted to stable β-nitrophenyl hydrazone D-erythrose (U U-C^ C) by p-nitrophenylhydrazine. The advantage of the proposed method for the preparation of D-erythrose (U-2-C) is its simplicity, low labor costs and the possibility of storing D-erythrose (U-C) in the form of its stable hydrazone. D-erythrosis / U-^ C / is an important substance in biochemical research and carbohydrate study. 201 336

Claims (1)

2 201 330 Příklad 1 K 1 ml 1 % roztoku vodorozpustného polysaeharidu /U-^C/ zo zelených rias o celko-vé j aktivitě 50/jGí sa přidalo 180 mg celulózového papiera Whatman 3 MM, obsahujúcehochemicky viazanú glukoamylézu /obsah proteinu 40 mg/g papiera o špecifickej aktivitě160 U/g nosiča připraveného podl'a čs. autorského osvedčenia č. 189472. Reakčné zmessa neché pretrepévať pri teplote 20 °C po dobu 6 hod. Po přeběhnutí reakcie sa glukoamy-láza zakotvené na papieri odfiltruje a zmes sa rozdělí na chromatografickom papieriWhatman No 1 v systéme octan etylnatý : 2-propanol : voda /6:2:1/. Ródiochemický výťažokD-glukózy /U-14C/ je 45 /íCi /90 %/. K tomuto množstvu sa přidá eáte 200 mg neaktivnějD-glukózy, rozpustí sa v 12,5 ml kyseliny octovej. Po přidaní 0,87 % octanu olovičitéhodo reakčného roztoku sa zmes neché stéť 10 min. pri laboratórnej teplote. Vzniknutý octanolovnatý sa vyzráža roztokom kyseliny šťavelovej /252 mg dihydrótu kyseliny sťavelovejv 2,8 ml Ityseliny octovej/, po 10 min. sa zrazenina odfiltruje a filtrát sa zahustí prizníženom tlaku pri 35 °C. K zvyšku sa přidá 10 ml octanu et.vlnatého, vypadnutá zrazeninasa odfiltruje a filtrát sa premyje 3 x 1 ml vody, vysuší so sírnanom sodným a zahustí. Získá sa 115 mg di-O-formyl-D-erytrózy /U-14C/, ktoré sa rozpustí v 11,5 ml 5 % kyselinyoctovej a nechá refluxovat 2 hod. Potom sa roztok zahustí pri zníženom tlaku a zvyšoksa trikrát odpaří s etanolom. Chromatografia v systéme octan etylnatý : kyselina octová : 4 % kyselina ortoborité ukazuje 97 % čistotu D-erytrózy /U-14C/ o aktivitě 23,4/iCi /52 %/.Výťažok 78,8 mg. Příprava p-NOg-fenylhydrazónu D-erytrózy 70 mg D-erytrózy /U-14C/ sa rozpustí v 10 ml etanolu, k roztoku sa přidá 89 mgp-NOg-fanylhydrazínu a zmes sa refluxuje 15 minút. Potom sa reakčná zmes zahustí na po-lovičný objem a nechá kryštalizovať. Vypadnuté kryštély sa prekryštali*zujú z vody,pričom sa získá 95,4 mg /64,8 %/ chromatograficky čistého p-NOg-fenylhydrazónu D-erytrózy/U-14C/ o t.t. = 208 až 210 °C. Příklad 2 Tak ako je uvedené v postupe podTa příkladu 1, s tým rozdielom, že hydrolýza vodo-rozpustného polysaeharidu /U-^C/ sa vykoná účinkom 1 N kyseliny chlorovodíkovéj pri100 °C po dobu 2 hod. Po odstránení kyseliny chlorovodíkovej sa získaný hydrolyzétpodrobí oxidatívněmu odbúraniu, tak ako je uvedené v příklade 1. PŘEĎME T V ϊ N X L E Z U Spdsob přípravy D-erytrózy /U-^4C/ z rédioaktívneho polysaeharidu a jej p-nitro--fenylhydrazónu vyznačujúci sa tým, že hydrolyzét, získaný z vodorozpustného polysacha-ridu /U-14C/ typu eC /1—4/ glukánu účinkom minerélnych kyselin alebo enzýmu gluko-amylázy, sa podrobí exidatívněmu odbúraniu octanom olovičitým a získané D-erytróza/U-14C/ sa rozpustí v etanole a refluxuje s p-nitro-fenyl-hydrazinom, zmes sa potom za- 3 201 330 hustí na polovičný objem a nechá kryštalizovať. OPRAVA popisu vynálezu k autorskému osvědčení č.201 336/51/ Int.Cl?C 07 H 3/02 V popisu vynálezu k autorskému osvědčení č.201 336 je chybau druhého autora v názvu bydliště. Místo! ..., ZEMEK JURAJ ing.CSo., LETONICA Správně: ZEMEK JURAJ ing.CSo., LEHNICA ÚŘAD PRO VYNÁLEZY A OBJEVYExample 1 To 1 ml of a 1% solution of water-soluble polysaccharide (U /C) from green algae with a total activity of 50 µg was added 180 mg of cellulose paper Whatman 3 MM containing chemically bound glucoamylase / protein content 40 mg / g of paper having a specific activity of 160 U / g of carrier prepared by MS. The reaction mixture was allowed to shake at 20 ° C for 6 hours. After the reaction had run out, the glucamylase anchored on the paper was filtered off and the mixture was separated on a chromatographic paper with No.1 in ethyl acetate: 2-propanol: water (6: 2: 1). Rhodochemical yield of D-glucose (U-14C) is 45 (Ci / 90%). To this amount was added 200 mg of inactive D-glucose, dissolved in 12.5 ml of acetic acid. After adding 0.87% lead acetate and the reaction solution, the mixture was allowed to stand for 10 min. at room temperature. The resulting acetanol is precipitated with a solution of oxalic acid / 252 mg of oxalic acid dihydrate in 2.8 ml of acetic acid (10 min). the precipitate was filtered off and the filtrate was concentrated under reduced pressure at 35 ° C. 10 ml of ethyl acetate are added to the residue, the precipitated precipitate is filtered off and the filtrate is washed with 3 x 1 ml of water, dried with sodium sulphate and concentrated. 115 mg of di-O-formyl-D-erythrose (U-14C) are obtained, which is dissolved in 11.5 ml of 5% acetic acid and refluxed for 2 hours. The solution is then concentrated under reduced pressure and the residue is evaporated three times with ethanol. Ethyl acetate: acetic acid: 4% orthoboric acid showed 97% purity of D-erythrose / U-14C (23.4 µCi / 52%) 78.8 mg. Preparation of D-erythrose p-NOg-phenylhydrazone 70 mg of D-erythrose (U-14C) is dissolved in 10 ml of ethanol, 89 mg of p-NOg-fanylhydrazine are added to the solution and refluxed for 15 minutes. Then the reaction mixture is concentrated to a volume volume and allowed to crystallize. The precipitated crystals are recrystallized from water to give 95.4 mg (64.8%) of D-erythrose (U-14C) pure p-NOg-phenylhydrazone (m.p. = 208-210 ° C. Example 2 As described in Example 1, except that the hydrolysis of the water-soluble polysaccharide (U-C) is carried out with 1 N hydrochloric acid at 100 ° C for 2 hours. oxidative degradation, as described in Example 1. EXAMPLES FOR NXLEZES Preparation of D-erythrose (U-4C) from the reductive polysaccharide and its p-nitro-phenylhydrazone, characterized in that the hydrolyzet obtained from the water-soluble polysaccharide (U-14C / type eC / 1-4) glucan by mineral acids or enzyme glucosylase, is subjected to exidative lead acetate dissolution and the obtained D-erythrose (U-14C) is dissolved in ethanol and refluxed with p-nitro-phenyl The hydrazine mixture is then inflated to half the volume and allowed to crystallize. REPAIR OF THE DESCRIPTION OF THE INVENTION FOR AUTHORIZED CERTIFICATE NO.201 336/51 / Int.Cl? C 07 H 3/02 In the description of the invention for author's certificate no. Place! ..., ZEMEK JURAJ ing.CSo., LETONICA Correct: ZEMEK JURAJ ing.CSo., LEHNICA OFFICE AND DISCOVERY
CS600578A 1978-09-18 1978-09-18 Method of preparing d-erythrose /u up 14c/ from radioactive polysaccharide /u up 14c/ and their p-nitro-phenyl-hydrazone CS201336B1 (en)

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