NO832858L - PROCEDURE FOR PREPARING RHAMNOSE OR FUCOSE - Google Patents
PROCEDURE FOR PREPARING RHAMNOSE OR FUCOSEInfo
- Publication number
- NO832858L NO832858L NO832858A NO832858A NO832858L NO 832858 L NO832858 L NO 832858L NO 832858 A NO832858 A NO 832858A NO 832858 A NO832858 A NO 832858A NO 832858 L NO832858 L NO 832858L
- Authority
- NO
- Norway
- Prior art keywords
- bacteria
- fucose
- genus
- rhamnose
- polysaccharide
- Prior art date
Links
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 19
- PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 title claims description 17
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 title claims description 16
- PNNNRSAQSRJVSB-KCDKBNATSA-N aldehydo-L-fucose Chemical compound C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-KCDKBNATSA-N 0.000 title 1
- PNNNRSAQSRJVSB-BXKVDMCESA-N aldehydo-L-rhamnose Chemical compound C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O PNNNRSAQSRJVSB-BXKVDMCESA-N 0.000 title 1
- 150000004676 glycans Chemical class 0.000 claims description 19
- 229920001282 polysaccharide Polymers 0.000 claims description 19
- 239000005017 polysaccharide Substances 0.000 claims description 19
- 241000894006 Bacteria Species 0.000 claims description 18
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 claims description 16
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 claims description 15
- 150000008266 deoxy sugars Chemical class 0.000 claims description 13
- 241000588914 Enterobacter Species 0.000 claims description 7
- 241000588748 Klebsiella Species 0.000 claims description 6
- 241000589516 Pseudomonas Species 0.000 claims description 6
- 238000000855 fermentation Methods 0.000 claims description 6
- 230000004151 fermentation Effects 0.000 claims description 6
- 241000588986 Alcaligenes Species 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 241000588697 Enterobacter cloacae Species 0.000 claims description 2
- 241000588747 Klebsiella pneumoniae Species 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- 230000015556 catabolic process Effects 0.000 claims 1
- 235000000346 sugar Nutrition 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000008103 glucose Substances 0.000 description 9
- 239000001963 growth medium Substances 0.000 description 7
- 229920002444 Exopolysaccharide Polymers 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000005862 Whey Substances 0.000 description 6
- 102000007544 Whey Proteins Human genes 0.000 description 6
- 108010046377 Whey Proteins Proteins 0.000 description 6
- 229930182830 galactose Natural products 0.000 description 6
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 5
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 description 2
- 241000588810 Alcaligenes sp. Species 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- 102000002322 Egg Proteins Human genes 0.000 description 2
- 108010000912 Egg Proteins Proteins 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229910001424 calcium ion Inorganic materials 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 235000014103 egg white Nutrition 0.000 description 2
- 210000000969 egg white Anatomy 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 241001135265 Cronobacter sakazakii Species 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
- 108010015776 Glucose oxidase Proteins 0.000 description 1
- 239000007836 KH2PO4 Substances 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 241000588746 Raoultella planticola Species 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229920006008 lipopolysaccharide Polymers 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- -1 methyl pentoses Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007320 rich medium Substances 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
Oppfinnelsen vedrører en fremgangsmåte til fremstilling av rhamnose eller fucose, idet fremgangsmåten erkarakterisert vedat man ved fermentering med bakterier av slekten Alcaligenes, Klebsiella, Pseudomonas eller Enterobacter frembringer et på disse desoksysukkere rikt ekstracellulært polysakkarid, hydrolyserer dette og adskiller de dannede desoksysukkere. The invention relates to a method for the production of rhamnose or fucose, the method being characterized by fermentation with bacteria of the genus Alcaligenes, Klebsiella, Pseudomonas or Enterobacter producing an extracellular polysaccharide rich in these deoxysugars, hydrolysing this and separating the formed deoxysugars.
Desoksysukrene rhamnose og fucose er bare meget vanskelig tilgjengelige på kjemisk vei. Det er kjent at tallrike bakterier er istand til å syntetisere desoksysukkere. Lipopolysakkarider inneholder meget ofte rhamnose og/eller fucose, likeledes tallrike ekstracellulære polysakkarider, imidlertid hver gang bare i meget små mengder. The deoxysugars rhamnose and fucose are only very difficult to obtain chemically. It is known that numerous bacteria are capable of synthesizing deoxysugars. Lipopolysaccharides very often contain rhamnose and/or fucose, likewise numerous extracellular polysaccharides, however each time only in very small amounts.
Det er nå funnet at bakterier av slektene Alcaligenes, Klebsiella, Pseudomonas og Enterobacter kan. syntetisere ekstracellulære polysakkarider som inneholder mer enn 10% rhamnose og/eller fucose og at disse desoksysukkere kan utvinnes fra de dannede polysakkarider også i gode utbytter.- It has now been found that bacteria of the genera Alcaligenes, Klebsiella, Pseudomonas and Enterobacter can. synthesize extracellular polysaccharides that contain more than 10% rhamnose and/or fucose and that these deoxysugars can be extracted from the formed polysaccharides also in good yields.-
I det følgende forklares nærmere foretrukne utførelses-former av oppfinnelsen. In the following, preferred embodiments of the invention are explained in more detail.
En utførelsesform av fremgangsmåten ifølge oppfinnelsen består i å fermentere en bakterie av slekten Alcaligenes i et sukkerrikt medium i luftet submerskultur, hydroly-sere det dannede polysakkarid etter foregående isolering og eventuelt tørking eller umiddelbart, og fra hydrolysatet å utvinne rhamnose. An embodiment of the method according to the invention consists in fermenting a bacterium of the genus Alcaligenes in a sugar-rich medium in an aerated submerged culture, hydrolyzing the formed polysaccharide after previous isolation and possibly drying or immediately, and extracting rhamnose from the hydrolyzate.
En annen utførelsesform ifølge oppfinnelsen bestårAnother embodiment according to the invention consists
i at en bakterie av slekten Pseudomonas, spesielt den fra EP-PS 12.552 kjente stamme ATCC 31.461, fermenteres, som omtalt og fra det rhamnoserike eksopolysakkarid isoleres rhamnosen. in that a bacterium of the genus Pseudomonas, especially the strain ATCC 31,461 known from EP-PS 12,552, is fermented, as mentioned, and rhamnose is isolated from the rhamnose-rich exopolysaccharide.
En annen utførelsesform ifølge oppfinnelsen bestårAnother embodiment according to the invention consists
i at en bakterie fra slekten Klebsiella, spesielt typen Klebsiella pneumoniae, fremfor alt den fra US-patent 4.350.769 kjente stamme ATCC 31.488, fermenteres som omtalt.og.fra.det in that a bacterium from the genus Klebsiella, especially the type Klebsiella pneumoniae, above all the strain ATCC 31,488 known from US patent 4,350,769, is fermented as described.and.from.it
fucoserike eksopolysakkarid isoleres fucosen. Tallrike ikke-patogene stammer ble i den senere tid uttatt av typen K. pneumoniae og tilordnet den nye type K. planticola. Uavhengig av fucose-rich exopolysaccharide fucosen is isolated. Numerous non-pathogenic strains were recently removed from the type K. pneumoniae and assigned to the new type K. planticola. Independent
denne nomenklatur vedrører denne utførelsesform av oppfinnelsen anvendelse av slike bakterier av slekten Klebsiella som danner fucoserike eksopolysakkarider. this nomenclature relates to this embodiment of the invention the use of such bacteria of the genus Klebsiella which form fucose-rich exopolysaccharides.
En ytterligere utførelsesform av oppfinnelsen består i å fermentere en bakterie av slekten Enterobacter, fortrinnsvis arten Enterobacter cloacae eller Enterobacter sakazaki, som nevnt ovenfor og fra det dannede polysakkarid å utvinne fucose. A further embodiment of the invention consists in fermenting a bacterium of the genus Enterobacter, preferably the species Enterobacter cloacae or Enterobacter sakazaki, as mentioned above and extracting fucose from the polysaccharide formed.
Utvalget av egnede stammer av de nevnte bakterie-typer foregår ved kromatografisk analyse av de dannede eksopolysakkarider som hydrolyseres på vanlig måte, eksempelvis ved papir-, tynnsjikt-, høytrykksvæske- eller gasskromatogra-fi av egnede derivater. The selection of suitable strains of the mentioned bacterial types takes place by chromatographic analysis of the exopolysaccharides formed which are hydrolysed in the usual way, for example by paper, thin layer, high pressure liquid or gas chromatography of suitable derivatives.
Som sukkerrike kulturmedier for ovennevnte fremgangsmåte tjener slike som som karbonkilde i det vesentlige inneholder glukose, sakkarose, laktose, galaktose, fruktose-eller andre sukkerholdige råstoffer som myse. Som nitrogenkilder tjener uorganiske salter som natriumnitrat eller ammoniumsalter og/eller organiske nitrogenkilder som mais-svellevann, gjærekstrakt, soyamel e.l. Anvendes myse som sukkerkilde, så kan på grunn av dens eggehviteinnhold meng-den av de øvrige nitrogenkilder nedsettes. Videre inneholder kulturmediene de vanlige salter og sporelementer. Those that essentially contain glucose, sucrose, lactose, galactose, fructose or other sugar-containing raw materials such as whey serve as sugar-rich culture media for the above-mentioned method. Inorganic salts such as sodium nitrate or ammonium salts and/or organic nitrogen sources such as corn-swell water, yeast extract, soy flour etc. serve as nitrogen sources. If whey is used as a sugar source, then due to its egg white content, the quantity of the other nitrogen sources can be reduced. Furthermore, the culture media contain the usual salts and trace elements.
Fermenteringsbetingelsene,tilsvarer de som er vanlige for bakterier av disse slekter. Temperaturen holdes i et område åå ca. 25 - ca. 40°C, spesielt ca. 30°C. pH-verdien innstilles på et område fra ca. 6 - 7,5, spesielt ca. 6,8, og holdes konstant. Kulturen luftes med ca. 1-2 liter, fortrinnsvis 1$ liter pr. minutt og pr. liter medium og om-røres. The fermentation conditions correspond to those common to bacteria of these genera. The temperature is kept in a range of approx. 25 - approx. 40°C, especially approx. 30°C. The pH value is set in a range from approx. 6 - 7.5, especially approx. 6.8, and is held constant. The culture is aerated with approx. 1-2 litres, preferably 1$ liter per minute and per liter of medium and stir.
Etter ca. 5-7 dager er sukkeret avbygget og bak-teriene har utskilt ca. 15 - 25 g polysakkarid pr. liter medium, minst ca. 20 g/l medium. Innholdet av rhamnose resp. fucose ligger ved ytelsesdyktige stammer over 20%, delvis over 50%. After approx. 5-7 days, the sugar has broken down and the bacteria have secreted approx. 15 - 25 g polysaccharide per liter of medium, at least approx. 20 g/l medium. The content of rhamnose resp. fucose is above 20%, partly above 50% in strains capable of performing.
Hydrolysen av polysakkaridene foregår på kjent måte, f.eks. med vandige syrer som saltsyre, svovelsyre, fosfor syre eller eddiksyre, hensiktsmessig ved forhøyet temperatur, fortrinnsvis ved ca. 80 - 120°C. The hydrolysis of the polysaccharides takes place in a known manner, e.g. with aqueous acids such as hydrochloric acid, sulfuric acid, phosphoric acid or acetic acid, suitably at an elevated temperature, preferably at approx. 80 - 120°C.
Hydrolysen er vanligvis avsluttet etter 4-10 timer. Alt etter typen av den anvendte syre, kan denne fjernes ved destillering eller nøytraliserende utfelling og den syrefrie sukkerholdige oppløsning oppdeles på kjent måte. The hydrolysis is usually finished after 4-10 hours. Depending on the type of acid used, this can be removed by distillation or neutralizing precipitation and the acid-free sugar-containing solution is divided in a known manner.
Alt etter hydrolysatets sammensetning foregår ut-skillelsen av det ønskede desoksysukker ved hjelp av kroma-tografiske metoder, eksempelvis ved ionutvekslerkromatogra-fi eller adsorbsjon på egnede overflaterike stoffer som zeolitter. En annen foretrukket opparbeidelse består i at hydrolysatet opparbeides fermentativt idet biproduktene av-bygges og det ønskede desoksysukker anrikes. Depending on the composition of the hydrolyzate, the separation of the desired deoxysugar takes place using chromatographic methods, for example by ion exchange chromatography or adsorption on suitable surface-rich substances such as zeolites. Another preferred processing consists in the hydrolyzate being processed fermentatively as the by-products are broken down and the desired deoxysugar is enriched.
De ifølge oppfinnelsen oppnåelige metylpentoser, rhamnose og fucose egner seg som utgangsstoff for fremstil-lingen av aromastoffer. The methyl pentoses, rhamnose and fucose obtainable according to the invention are suitable as starting materials for the production of flavoring substances.
Ic.de følgende eksempler refererer prosentangivel-sene seg til vekt hvis intet annet er angitt. In the following examples, the percentages refer to weight if nothing else is stated.
Eksempel 1Example 1
Alcaligenes sp. dyrkes i et kulturmedium som pr. liter inneholder følgende stoffer: Alcaligenes sp. grown in a culture medium which per liter contains the following substances:
Kulturens temperatur innstilles på 30°C og pH-verdien på 6,8 og holdes konstant. Den omrørte kultur for-sørges med 1,5 liter luft pr. minutt og pr. liter medium. The temperature of the culture is set at 30°C and the pH at 6.8 and kept constant. The stirred culture is supplied with 1.5 liters of air per minute and per liter medium.
Etter 6 dager er sukkeret aybygget.^After 6 days, the sugar is aybygged.^
Pr. liter kulturmedium ble det utskilt ca. 20 g polysakkarid som bestod til ca. 50% av rhamnose, 30% glukose, 15% galaktose samt ca. 5% fucose. Per liter of culture medium, approx. 20 g of polysaccharide which consisted of approx. 50% of rhamnose, 30% glucose, 15% galactose and approx. 5% fucose.
Polysakkaridet ble hydrolysert med vandig saltsyre ved ca. 100°C i løpet av 6 timer. Deretter ble klorhydro-genet fjernet ved destillering. The polysaccharide was hydrolysed with aqueous hydrochloric acid at approx. 100°C within 6 hours. The hydrogen chloride was then removed by distillation.
Det nøytrale hydrolysat fortynnes til en sukker-konsentrasjon på ca. 20% med vann og tilsettes 1% gjærekstrakt, 0,6% urinstoff, 0,12% KH2P04og 0,018% Na2HP04. The neutral hydrolyzate is diluted to a sugar concentration of approx. 20% with water and add 1% yeast extract, 0.6% urea, 0.12% KH2PO4 and 0.018% Na2HP04.
Etter innstilling av pH-verdien på 6,0 - 6,5 podes med en gjær av typen Saccharomyces cerevisiae som forgjærer gly-kosen og galaktosen fra det spaltede polysakkarid under an-aerobe betingelser ved 30 - 37°C til etanol og lar det bli tilbake desoksysukker. After setting the pH value to 6.0 - 6.5, it is inoculated with a yeast of the type Saccharomyces cerevisiae which preferments the glucose and galactose from the cleaved polysaccharide under anaerobic conditions at 30 - 37°C to ethanol and allows it to become back deoxysugar.
I kulturmediet kan i stedet for glukose som sukker også anvendes sakkarose, laktose, galaktose, mannose, fruk-tose eller myse, idet i tilfellet myse etter bestemmelse av laktoseinhholdet det likeledes anvendes ca.. 50 g sukker pr. liter. På grunn av mysens eggehviteinnhold reduseres meng-den av kornstøp pg NaNO^tilsvarende. Man får således mellom 15 og 25 g polysakkarid pr. liter som til 40 -60% består av rhamnose, 20 - 40% av glukose, 10 - 20% av galaktose samt 1-5% fucose. In the culture medium, instead of glucose as sugar, sucrose, lactose, galactose, mannose, fructose or whey can also be used, in the case of whey after determining the lactose content, approx. 50 g of sugar per litres. Due to the whey's egg white content, the amount of grain cast is reduced by NaNO^ correspondingly. You thus get between 15 and 25 g of polysaccharide per liter which consists of 40-60% rhamnose, 20-40% glucose, 10-20% galactose and 1-5% fucose.
Hydrolysen kan istedenfor med saltsyre også foregå med svovelsyre, fosforsyre eller eddiksyre ved 80 - 120°C i løpet av 4 - 10 timer. Etter hydrolysen kan eddiksyren som saltsyren fjernes ved destillering, mens svovelsyre og fosforsyre kan adskilles ved hjelp av kalsiumioner. Instead of using hydrochloric acid, the hydrolysis can also take place with sulfuric acid, phosphoric acid or acetic acid at 80 - 120°C during 4 - 10 hours. After the hydrolysis, the acetic acid and the hydrochloric acid can be removed by distillation, while sulfuric acid and phosphoric acid can be separated using calcium ions.
Adskillelsen av glukose og galaktose fra hydrolysatet ved gjæring kan istedenfor med Saccharomyces cerevisiae også foregå med andre gjærtyper, enkeltvis, eller, sammen. The separation of glucose and galactose from the hydrolyzate by fermentation can, instead of with Saccharomyces cerevisiae, also take place with other yeast types, individually or together.
Fra hydrolysatet kan glukosen også ved hjelp av enzymet glukoseoksydase i nærvær av oksygen overføres i glukonsyre som kan adskilles ved pH 11 - 12 med kalsium-eller magnesiumioner i form av tungt oppløselige salter.' Herved forblir det ikke omsatte sukker oppløst i det over-stående, hvorfra det isoleres, og hvis nødvendig, kan adskilles ved kjente metoder. From the hydrolyzate, the glucose can also be transferred with the aid of the enzyme glucose oxidase in the presence of oxygen into gluconic acid, which can be separated at pH 11 - 12 with calcium or magnesium ions in the form of poorly soluble salts.' Hereby, the unreacted sugar remains dissolved in the supernatant, from which it is isolated and, if necessary, can be separated by known methods.
Eksempel 2Example 2
Eksempel 1 modifiseres således at kulturmediet istedenfor NaNO^og KH2?04pr. liter inneholder 1 g gjæreks trakt og istedenfor 1,5 g kornstøp inneholder 2 g. Videre anvendes istedenfor Alcaligenes sp. Enterobacter sakazaki. Fermenteringspararaetrene stemmer overens med eksempel 1. Example 1 is modified so that the culture medium instead of NaNO^ and KH2?04pr. liter contains 1 g yeast funnel and instead of 1.5 g grain cast contains 2 g. Furthermore, instead of Alcaligenes sp. Enterobacter sakazakii. The fermentation parameters correspond to Example 1.
I kulturen dannes etter 6 dager 16 g polysakkarid pr. liter idet glukosen er avbygget til 9 5%. Polysakkaridet inneholder ca. 30% fucose. In the culture, after 6 days, 16 g of polysaccharide per liter as the glucose has broken down to 95%. The polysaccharide contains approx. 30% fucose.
Arbeider man istedenfor glukose med andre i eksempel 1 nevnte sukkere resp. myse, så får man i løpet av 5 - 7 dager pr. liter kulturmedium 12 - 18 g polysakkarid som inneholder 20 - 40% fucose. If you work instead of glucose with other sugars mentioned in example 1 or whey, then you get within 5 - 7 days per liter of culture medium 12 - 18 g polysaccharide containing 20 - 40% fucose.
Eksempel 3Example 3
Det ifølge eksempel 1 i EP-PS 12.552 dannede rhamnoserike eksopolysakkarid opparbeides ifølge eksempel 1 og rhamnosen isoleres. The rhamnose-rich exopolysaccharide formed according to example 1 in EP-PS 12,552 is worked up according to example 1 and the rhamnose is isolated.
Eksempel 4Example 4
Etter angivelsen i U.S. patent 4.350.769 frembringes et fucoserikt eksopolysakkarid og opparbeides ifølge eksempel 1. Following the listing in the U.S. patent 4,350,769, a fucose-rich exopolysaccharide is produced and processed according to example 1.
Claims (13)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3229700 | 1982-08-10 | ||
| DE3300633A DE3300633A1 (en) | 1982-08-10 | 1983-01-11 | METHOD FOR PRODUCING RHAMNOSE OR FUCOSE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO832858L true NO832858L (en) | 1984-02-13 |
Family
ID=25803655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO832858A NO832858L (en) | 1982-08-10 | 1983-08-09 | PROCEDURE FOR PREPARING RHAMNOSE OR FUCOSE |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0102535A2 (en) |
| AU (1) | AU1782083A (en) |
| BR (1) | BR8304279A (en) |
| DD (1) | DD210074A5 (en) |
| DE (1) | DE3300633A1 (en) |
| DK (1) | DK363483A (en) |
| ES (1) | ES524806A0 (en) |
| FI (1) | FI832848A (en) |
| GR (1) | GR78922B (en) |
| IL (1) | IL69444A0 (en) |
| NO (1) | NO832858L (en) |
| OA (1) | OA07517A (en) |
| PT (1) | PT77172B (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2574429B1 (en) * | 1984-12-06 | 1987-12-11 | Roussel Uclaf | ACYLGLYCANNES EXTRACTED FROM KLEBSIELLA, PROCESS FOR OBTAINING THEM, THEIR APPLICATION AS MEDICAMENTS AND THE COMPOSITIONS CONTAINING THEM |
| JPS61146200A (en) * | 1984-12-20 | 1986-07-03 | 呉羽化学工業株式会社 | High purity separation of ramnose from gum arabic |
| US4806636A (en) * | 1985-03-20 | 1989-02-21 | The Dow Chemical Company | Heteropolysaccharide produced by Enterobacter sakazakii |
| JPS62126193A (en) * | 1985-11-26 | 1987-06-08 | Towa Kasei Kogyo Kk | Production of l-rhamnose |
| US4933281A (en) * | 1987-03-17 | 1990-06-12 | The University Of Iowa Research Foundation | Method for producing rhamnose |
| FR2624522B1 (en) * | 1987-12-11 | 1990-03-09 | Bioeurope | CULTURE OF A KLEBSIELLA SP. MICROORGANISM, AND PROCESS FOR PRODUCING A MIXTURE OF BONES WITH A HIGH RHAMNOSE CONTENT USING THIS CULTURE |
| EP0339445A1 (en) * | 1988-04-27 | 1989-11-02 | Hoechst Aktiengesellschaft | Rhamnose-containing polysaccharide, process for its preparation and its use |
| US7037378B2 (en) | 2003-09-24 | 2006-05-02 | Danisco Sweetners Oy | Separation of sugars |
| IT1405680B1 (en) | 2010-09-13 | 2014-01-24 | Inalco Spa | PROCESS FOR THE PRODUCTION OF L-FUCOSIUM. |
| ITFI20120052A1 (en) | 2012-03-13 | 2013-09-14 | Inalco Spa | PROCESS FOR RECOVERY OF L-FUCOSIO FROM ESOPOLISACCARIDES. |
| US9902984B2 (en) | 2013-09-06 | 2018-02-27 | Glycom A/S | Fermentative production of oligosaccharides |
| EP3486326A1 (en) | 2017-11-21 | 2019-05-22 | Jennewein Biotechnologie GmbH | Method for the purification of n-acetylneuraminic acid from a fermentation broth |
-
1983
- 1983-01-11 DE DE3300633A patent/DE3300633A1/en not_active Withdrawn
- 1983-08-05 EP EP83107721A patent/EP0102535A2/en not_active Withdrawn
- 1983-08-08 PT PT77172A patent/PT77172B/en unknown
- 1983-08-08 GR GR72164A patent/GR78922B/el unknown
- 1983-08-08 ES ES524806A patent/ES524806A0/en active Granted
- 1983-08-08 IL IL69444A patent/IL69444A0/en unknown
- 1983-08-08 DD DD83253796A patent/DD210074A5/en unknown
- 1983-08-08 FI FI832848A patent/FI832848A/en not_active Application Discontinuation
- 1983-08-09 AU AU17820/83A patent/AU1782083A/en not_active Abandoned
- 1983-08-09 NO NO832858A patent/NO832858L/en unknown
- 1983-08-09 BR BR8304279A patent/BR8304279A/en unknown
- 1983-08-09 DK DK363483A patent/DK363483A/en not_active Application Discontinuation
- 1983-08-10 OA OA58084A patent/OA07517A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT77172B (en) | 1986-03-27 |
| ES8404412A1 (en) | 1984-05-01 |
| FI832848A (en) | 1984-02-11 |
| ES524806A0 (en) | 1984-05-01 |
| GR78922B (en) | 1984-10-02 |
| EP0102535A2 (en) | 1984-03-14 |
| DK363483A (en) | 1984-02-11 |
| FI832848A0 (en) | 1983-08-08 |
| AU1782083A (en) | 1984-02-16 |
| PT77172A (en) | 1983-09-01 |
| OA07517A (en) | 1985-03-31 |
| DD210074A5 (en) | 1984-05-30 |
| IL69444A0 (en) | 1983-11-30 |
| BR8304279A (en) | 1984-03-20 |
| DK363483D0 (en) | 1983-08-09 |
| DE3300633A1 (en) | 1984-03-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BE533886A (en) | ||
| NO832858L (en) | PROCEDURE FOR PREPARING RHAMNOSE OR FUCOSE | |
| AU558746B2 (en) | A method for producing ethanol from xylose-containing substance | |
| JPS63112965A (en) | Production of yeast extract | |
| Gibbs et al. | Pullulan | |
| DE102011003394A1 (en) | Process for the fermentative production of 2,3-butanediol | |
| JPH0787987A (en) | Preparation of vanillin by biological conversion of benzenoid precursor | |
| GB1564020A (en) | Method of producting a polysaccharide through fermentation and the product obtained thereby | |
| US5686277A (en) | Fermentation process for preparing xylitol using mutant cells | |
| US6287830B1 (en) | Fermentation process for preparing erythritol by a high salt tolerant mutant of Candida sp. | |
| Park et al. | Fungal invertase as an aid for fermentation of cane molasses into ethanol | |
| DE102013216658A1 (en) | Process for the fermentative production of C4 products and microorganism strains suitable therefor | |
| AU597264B2 (en) | Fermentation process for the production of fructose from aqueous mixtures of fructose and glucose and zymomonas mobilis mutants which can be used for such fermentation | |
| US8871476B2 (en) | Process for production of fructo-oligosaccharides | |
| JP4055228B2 (en) | Method for producing erythritol | |
| DE69930071T2 (en) | Fermentation process for the production of erythritol by means of a mutant of Candida sp. with high salt tolerance | |
| JP4194152B2 (en) | Method for producing erythritol | |
| JPS5951798A (en) | Production of ramnose and fucose | |
| JPS6363390A (en) | Production of mannosyl erythritol | |
| NO802863L (en) | PROCEDURE FOR THE PREPARATION OF 2,5-DICETOGLUCONIC ACID | |
| JP3376859B2 (en) | Method for producing ribitol | |
| JPH02291293A (en) | Production of ethyl-alpha-glucoside | |
| KR890002698B1 (en) | Heteropoly saccharide s-184 and process for preparation thereof | |
| Park | The Preparation of Crystalline OD-Mannopyranosyl-(1→ 4)-O-D-Glucopyranosyl-(1→ 4)-D-Mannopyranose (MGM) from Konjac Glucomannan Using Xylogone sphaerospora β-mannanase System and Candida guilliermondii Fermentation | |
| JP2002000283A (en) | Method of fermentation for producing erythriitol by high-salt-tolerant mutant of candida bacterial strain |