DK1405856T3 - Krystaller af oligosaccharider og fremgangsmåder til fremstilling heraf - Google Patents
Krystaller af oligosaccharider og fremgangsmåder til fremstilling heraf Download PDFInfo
- Publication number
- DK1405856T3 DK1405856T3 DK02733463.0T DK02733463T DK1405856T3 DK 1405856 T3 DK1405856 T3 DK 1405856T3 DK 02733463 T DK02733463 T DK 02733463T DK 1405856 T3 DK1405856 T3 DK 1405856T3
- Authority
- DK
- Denmark
- Prior art keywords
- oligosaccharide
- crystals
- gal
- glcnac
- fuc
- Prior art date
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- 150000002482 oligosaccharides Chemical class 0.000 title claims description 112
- 229920001542 oligosaccharide Polymers 0.000 title claims description 108
- 239000013078 crystal Substances 0.000 title claims description 94
- 238000000034 method Methods 0.000 title claims description 57
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 37
- 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 35
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 claims description 35
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 claims description 35
- OVRNDRQMDRJTHS-RTRLPJTCSA-N N-acetyl-D-glucosamine Chemical group CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-RTRLPJTCSA-N 0.000 claims description 32
- MBLBDJOUHNCFQT-UHFFFAOYSA-N N-acetyl-D-galactosamine Natural products CC(=O)NC(C=O)C(O)C(O)C(O)CO MBLBDJOUHNCFQT-UHFFFAOYSA-N 0.000 claims description 31
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 claims description 31
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 claims description 30
- CERZMXAJYMMUDR-UHFFFAOYSA-N neuraminic acid Natural products NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO CERZMXAJYMMUDR-UHFFFAOYSA-N 0.000 claims description 29
- OVRNDRQMDRJTHS-KEWYIRBNSA-N N-acetyl-D-galactosamine Chemical compound CC(=O)N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O OVRNDRQMDRJTHS-KEWYIRBNSA-N 0.000 claims description 28
- SQVRNKJHWKZAKO-LUWBGTNYSA-N N-acetylneuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)CC(O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-LUWBGTNYSA-N 0.000 claims description 28
- 229940060155 neuac Drugs 0.000 claims description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 239000007864 aqueous solution Substances 0.000 claims description 25
- 238000011282 treatment Methods 0.000 claims description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 239000003960 organic solvent Substances 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 17
- 229920005989 resin Polymers 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 238000001179 sorption measurement Methods 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 11
- 150000008266 deoxy sugars Chemical group 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 7
- 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 claims description 3
- OVRNDRQMDRJTHS-CBQIKETKSA-N N-Acetyl-D-Galactosamine Chemical compound CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@H](O)[C@@H]1O OVRNDRQMDRJTHS-CBQIKETKSA-N 0.000 claims description 3
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 claims description 3
- SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 claims description 3
- 229930182830 galactose Natural products 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- 229950006780 n-acetylglucosamine Drugs 0.000 claims description 3
- WQZGKKKJIJFFOK-FPRJBGLDSA-N beta-D-galactose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-FPRJBGLDSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 30
- 150000002772 monosaccharides Chemical group 0.000 description 27
- 150000002337 glycosamines Chemical group 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000843 powder Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 5
- 229930182470 glycoside Natural products 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 4
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- 238000007876 drug discovery Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000001963 growth medium Substances 0.000 description 4
- 235000013402 health food Nutrition 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 3
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000011033 desalting Methods 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 3
- 230000004151 fermentation Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000001144 powder X-ray diffraction data Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 2
- MSWZFWKMSRAUBD-CBPJZXOFSA-N 2-amino-2-deoxy-D-mannopyranose Chemical compound N[C@@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-CBPJZXOFSA-N 0.000 description 2
- MSFSPUZXLOGKHJ-PGYHGBPZSA-N 2-amino-3-O-[(R)-1-carboxyethyl]-2-deoxy-D-glucopyranose Chemical compound OC(=O)[C@@H](C)O[C@@H]1[C@@H](N)C(O)O[C@H](CO)[C@H]1O MSFSPUZXLOGKHJ-PGYHGBPZSA-N 0.000 description 2
- CERZMXAJYMMUDR-QBTAGHCHSA-N 5-amino-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid Chemical compound N[C@@H]1[C@@H](O)CC(O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO CERZMXAJYMMUDR-QBTAGHCHSA-N 0.000 description 2
- WQZGKKKJIJFFOK-CBPJZXOFSA-N D-Gulose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-CBPJZXOFSA-N 0.000 description 2
- AEMOLEFTQBMNLQ-YMDCURPLSA-N D-galactopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-YMDCURPLSA-N 0.000 description 2
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 2
- 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 2
- 241000195522 Fucales Species 0.000 description 2
- WQZGKKKJIJFFOK-VSOAQEOCSA-N L-altropyranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-VSOAQEOCSA-N 0.000 description 2
- 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 description 2
- LFTYTUAZOPRMMI-UHFFFAOYSA-N UNPD164450 Natural products O1C(CO)C(O)C(O)C(NC(=O)C)C1OP(O)(=O)OP(O)(=O)OCC1C(O)C(O)C(N2C(NC(=O)C=C2)=O)O1 LFTYTUAZOPRMMI-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 238000002523 gelfiltration Methods 0.000 description 2
- 229960002442 glucosamine Drugs 0.000 description 2
- 229940097043 glucuronic acid Drugs 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- LFTYTUAZOPRMMI-LSIJYXAZSA-N uridine-diphosphate-n-acetylglucosamine Chemical compound O1[C@@H](CO)[C@H](O)[C@@H](O)[C@H](NC(=O)C)[C@@H]1O[P@](O)(=O)O[P@](O)(=O)OC[C@H]1[C@H](O)[C@@H](O)[C@H](N2C(NC(=O)C=C2)=O)O1 LFTYTUAZOPRMMI-LSIJYXAZSA-N 0.000 description 2
- -1 ΘΙοΝΑοβΙ Chemical class 0.000 description 2
- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- 101100313763 Arabidopsis thaliana TIM22-2 gene Proteins 0.000 description 1
- WQZGKKKJIJFFOK-WHZQZERISA-N D-aldose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-WHZQZERISA-N 0.000 description 1
- WQZGKKKJIJFFOK-IVMDWMLBSA-N D-allopyranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-IVMDWMLBSA-N 0.000 description 1
- ZCLAHGAZPPEVDX-UHFFFAOYSA-N D-panose Natural products OC1C(O)C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC1COC1C(O)C(O)C(O)C(CO)O1 ZCLAHGAZPPEVDX-UHFFFAOYSA-N 0.000 description 1
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 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 1
- 239000005715 Fructose Substances 0.000 description 1
- RTVRUWIBAVHRQX-PMEZUWKYSA-N Fucosyllactose Chemical compound C([C@H]1O[C@@H]([C@H]([C@@H](O[C@@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@@H]1O)O)OC)O[C@H]1OC[C@@H](O)[C@H](O)[C@@H]1O RTVRUWIBAVHRQX-PMEZUWKYSA-N 0.000 description 1
- 101001055216 Homo sapiens Interleukin-9 Proteins 0.000 description 1
- 102100026871 Interleukin-9 Human genes 0.000 description 1
- 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 1
- MSFSPUZXLOGKHJ-UHFFFAOYSA-N Muraminsaeure Natural products OC(=O)C(C)OC1C(N)C(O)OC(CO)C1O MSFSPUZXLOGKHJ-UHFFFAOYSA-N 0.000 description 1
- OVRNDRQMDRJTHS-ZTVVOAFPSA-N N-acetyl-D-mannosamine Chemical compound CC(=O)N[C@@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-ZTVVOAFPSA-N 0.000 description 1
- OVRNDRQMDRJTHS-OZRXBMAMSA-N N-acetyl-beta-D-mannosamine Chemical compound CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-OZRXBMAMSA-N 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- HSCJRCZFDFQWRP-ABVWGUQPSA-N UDP-alpha-D-galactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C(NC(=O)C=C2)=O)O1 HSCJRCZFDFQWRP-ABVWGUQPSA-N 0.000 description 1
- HSCJRCZFDFQWRP-UHFFFAOYSA-N Uridindiphosphoglukose Natural products OC1C(O)C(O)C(CO)OC1OP(O)(=O)OP(O)(=O)OCC1C(O)C(O)C(N2C(NC(=O)C=C2)=O)O1 HSCJRCZFDFQWRP-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000835 electrochemical detection Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- ZCLAHGAZPPEVDX-MQHGYYCBSA-N panose Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)O[C@@H]1CO[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 ZCLAHGAZPPEVDX-MQHGYYCBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 150000004044 tetrasaccharides Chemical class 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
- C07H5/06—Aminosugars
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (11)
1. Fremgangsmåde til fremstilling af krystaller af et oligosaccharid, hvilken fremgangsmåde omfatter tilsætning af en vandig opløsning, som indeholder et oligosaccharid, der er angivet ved den almene formel (I): R1 R2 R3 R4 Gal β 1,4Glc (I) I R5 [hvor Gal betegner galactose (i det følgende forkortet på samme måde), Glc betegner glucose (i det følgende forkortet på samme måde), R1 betegner GlcNAc (hvor GlcNAc betegner N-acetylglucosamin, der i det følgende forkortes på samme måde), NeuAc (hvor NeuAc betegner N-acetylneuraminsyre, der i det følgende forkortes på samme måde), Gal, Fuc (hvor Fuc betegner fucose, der i det følgende forkortes på samme måde) eller GalNAc (hvor GalNAc betegner N-acetylgalactosamin, der i det følgende forkortes på samme måde) , R2, R3 og R4, som kan være identiske eller forskellige, hver betegner en enkeltbinding, GlcNAc, NeuAc, Gal, Fuc eller GalNAc, og R5 betegner et hydrogenatom, GlcNAc, NeuAc, Gal, Fuc eller GalNAc] til et vandblandbart organisk opløsningsmiddel, hvor det vandblandbare organiske opløsningsmiddel er methanol eller acetone.
2. Fremgangsmåde til fremstilling af krystaller af et oligosaccharid ifølge krav 1, hvor R2, R3 og R4, som kan være identiske eller forskellige, hver er GlcNAc, NeuAc, Gal, Fuc eller GalNAc.
3. Fremgangsmåde til fremstilling af krystaller af et oligosaccharid ifølge krav 1, hvor R4 er en enkeltbinding.
4. Fremgangsmåde til fremstilling af krystaller af et oligosaccharid ifølge krav 1, hvor R3 og R4 hver er en enkeltbinding.
5. Fremgangsmåde til fremstilling af krystaller af et oligosaccharid ifølge krav 1, hvor R2, R3 og R4 hver er en enkeltbinding.
6. Fremgangsmåde til fremstilling af krystaller af et oligosaccharid ifølge krav 3, hvor R1 er GlcNAc, R2 er Gal, R3 er GlcNAc og R5 er et hydrogenatom.
7. Fremgangsmåde til fremstilling af krystaller af et oligosaccharid ifølge krav 4, hvor R1 er NeuAc eller Gal, R2 er GlcNAc eller GalNAc og R5 er et hydrogenatom.
8. Fremgangsmåde til fremstilling af krystaller af et oligosaccharid ifølge krav 5, hvor R1 er GlcNAc, Gal, NeuAc eller Fuc, og R5 er et hydrogenatom eller GalNAc.
9. Fremgangsmåde til fremstilling af krystaller af et oligosaccharid ifølge krav 1, hvor i det mindste én af R1, R2, R3, R4 og R5 er en deoxysukkerrest, og den vandige opløsning, der indeholder et oligosaccharid, er en vandig opløsning, der opnås ved behandling med en syntetisk adsorptionsharpiks.
10. Fremgangsmåde til fremstilling af krystaller af et oligosaccharid ifølge krav 9, hvor deoxysukkerresten er Fuc.
11. Fremgangsmåde til fremstilling af krystaller af et oligosaccharid ifølge krav 9, hvor R1 er Fuc, R2, R3 og R4 hver er en enkeltbinding, og R5 er et hydrogenatom.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001175930 | 2001-06-11 | ||
| PCT/JP2002/005787 WO2002100875A1 (fr) | 2001-06-11 | 2002-06-11 | Cristaux d'oligosaccharides et procedes de preparation correspondants |
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| Publication Number | Publication Date |
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| DK1405856T3 true DK1405856T3 (da) | 2019-01-07 |
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| DK02733463.0T DK1405856T3 (da) | 2001-06-11 | 2002-06-11 | Krystaller af oligosaccharider og fremgangsmåder til fremstilling heraf |
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| US (1) | US20040149200A1 (da) |
| EP (1) | EP1405856B1 (da) |
| JP (1) | JP4347042B2 (da) |
| KR (1) | KR100907590B1 (da) |
| CN (1) | CN100509830C (da) |
| CA (1) | CA2449736A1 (da) |
| DK (1) | DK1405856T3 (da) |
| ES (1) | ES2698398T3 (da) |
| WO (1) | WO2002100875A1 (da) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| TW200800354A (en) * | 2005-10-28 | 2008-01-01 | Kyowa Hakko Kogyo Kk | Concentration crystallizer and method |
| JPWO2007052787A1 (ja) * | 2005-11-07 | 2009-04-30 | 協和発酵バイオ株式会社 | 結晶またはアモルファスの洗浄方法および洗浄装置 |
| US8993740B2 (en) | 2010-02-19 | 2015-03-31 | Glycom A/S | Method for preparation of the tetrasaccharide lacto-N-neotetraose (LNnt) containing N-acetyllactosamine |
| IL207945A0 (en) | 2010-09-02 | 2010-12-30 | Robert Jansen | Method for the production of carbohydrates |
| US20130005954A1 (en) * | 2011-06-28 | 2013-01-03 | Apicore, Llc | Process for preparing heparinoids and intermediates useful in the synthesis thereof |
| WO2014086373A1 (en) | 2012-12-07 | 2014-06-12 | Glycom A/S | Crystallisation of human milk oligosaccharides (hmo) |
| DE202013012839U1 (de) | 2012-12-18 | 2020-05-15 | Glycom A/S | Neue Polymorphe von LNnT |
| ES2929571T3 (es) | 2014-08-22 | 2022-11-30 | Isothrive Inc | Proceso para la producción de isomaltooligosacáridos |
| CA2969748A1 (en) | 2014-08-22 | 2016-02-25 | Isothrive Llc | Process for the production of isomaltooligosaccharides |
| ES2933616T3 (es) | 2014-12-16 | 2023-02-10 | Glycom As | Separación de 2'-FL de un caldo de fermentación |
| US10696705B2 (en) | 2015-12-17 | 2020-06-30 | Glycom A/S | Crystalline forms of LNT |
| US11419884B2 (en) | 2016-06-24 | 2022-08-23 | Glycom A/S | Compositions comprising HMOS, their production and use for the prevention and/or treatment of viral and/or bacterial infections |
| CN119192256A (zh) * | 2016-10-31 | 2024-12-27 | 格礼卡姆股份公司 | 从结晶寡糖除去残余有机溶剂的方法 |
| EP3645545A4 (en) | 2017-06-30 | 2021-05-05 | Glycom A/S | PURIFICATION OF OLIGOSACCHARIDES |
| CN119655445A (zh) | 2017-07-12 | 2025-03-21 | 格礼卡姆股份公司 | 包含中性单糖或寡糖和酸性非碳水化合物组分的无定形混合物 |
| PT3897902T (pt) * | 2018-12-19 | 2023-12-06 | Glycom As | Separação de oligossacáridos |
| US20250051814A1 (en) | 2021-12-21 | 2025-02-13 | Kyowa Hakko Bio Co., Ltd. | Method for producing sugar including lacto-n-triose ii as core trisaccharide and method for producing crystals of said sugar |
| DK181566B1 (en) | 2021-12-21 | 2024-05-24 | Dsm Ip Assets Bv | Crystallization of LNnT |
| WO2023175130A1 (en) | 2022-03-17 | 2023-09-21 | Dsm Ip Assets B.V. | Crystalline lacto-n-triose ii |
| EP4502168A1 (en) | 2022-03-25 | 2025-02-05 | Kirin Holdings Kabushiki Kaisha | Production method for lactodifucotetraose (ldft) |
| CN117003803B (zh) * | 2022-05-07 | 2026-05-26 | 恒睿（青岛）生物科技有限公司 | 一种三糖的晶型 |
| CN115873051B (zh) * | 2022-05-17 | 2024-06-25 | 山东恒鲁生物科技有限公司 | 三糖的新晶型 |
| WO2025012361A1 (en) | 2023-07-11 | 2025-01-16 | Chr. Hansen A/S | Crystallization of lacto-n-triose ii |
| KR20250118895A (ko) | 2024-01-30 | 2025-08-07 | 경희대학교 산학협력단 | 아밀로수크라제를 이용한 수용성 아밀로오스 제조방법 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS56115796A (en) * | 1980-02-18 | 1981-09-11 | Rikagaku Kenkyusho | Novel oligosaccharide and its preparation |
| JPS60232095A (ja) * | 1984-05-01 | 1985-11-18 | Norin Suisansyo Shokuhin Sogo Kenkyusho | オリゴ糖還元物の結晶およびその製造方法 |
| JPS63109789A (ja) * | 1986-10-27 | 1988-05-14 | Yakult Honsha Co Ltd | オリゴ糖の製造法 |
| JPS63246391A (ja) * | 1987-04-01 | 1988-10-13 | Nisshin Seito Kk | 新規オリゴ糖類 |
| US5158939A (en) * | 1989-07-21 | 1992-10-27 | Wisconsin Alumni Research Foundation | Method of stimulating the immune systems of animals and compositions useful therefor |
| JPH0670075B2 (ja) * | 1990-08-28 | 1994-09-07 | ホクレン農業協同組合連合会 | １―ケストース結晶およびその製造方法 |
| JP3623974B2 (ja) * | 1993-09-13 | 2005-02-23 | カルピス株式会社 | オリゴ糖類の精製方法 |
| EP0670327B1 (en) * | 1994-03-01 | 1998-10-21 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Crystalline maltotetraosyl glucoside, and its production and use |
| JPH11221079A (ja) * | 1998-02-04 | 1999-08-17 | Kyowa Hakko Kogyo Co Ltd | 糖転移酵素および該酵素をコードするｄｎａ |
| JP2000279191A (ja) * | 1999-03-31 | 2000-10-10 | Snow Brand Milk Prod Co Ltd | オリゴ糖の製造法 |
| JP3611110B2 (ja) | 2001-03-19 | 2005-01-19 | 株式会社八十二銀行 | 先日付完結処理のシステム、方法、プログラム及びこれに用いる取消再カットメイン処理用プログラム並びに資源利用最適化システム、プログラム及びこれに用いる取消再実行メイン処理用プログラム |
-
2002
- 2002-06-11 CN CNB028086082A patent/CN100509830C/zh not_active Expired - Lifetime
- 2002-06-11 WO PCT/JP2002/005787 patent/WO2002100875A1/ja not_active Ceased
- 2002-06-11 KR KR1020037016131A patent/KR100907590B1/ko not_active Expired - Lifetime
- 2002-06-11 JP JP2003503641A patent/JP4347042B2/ja not_active Expired - Lifetime
- 2002-06-11 US US10/479,050 patent/US20040149200A1/en not_active Abandoned
- 2002-06-11 CA CA002449736A patent/CA2449736A1/en not_active Abandoned
- 2002-06-11 ES ES02733463T patent/ES2698398T3/es not_active Expired - Lifetime
- 2002-06-11 EP EP02733463.0A patent/EP1405856B1/en not_active Expired - Lifetime
- 2002-06-11 DK DK02733463.0T patent/DK1405856T3/da active
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002100875A1 (fr) | 2002-12-19 |
| KR100907590B1 (ko) | 2009-07-14 |
| EP1405856A4 (en) | 2007-01-03 |
| ES2698398T3 (es) | 2019-02-04 |
| CN1503803A (zh) | 2004-06-09 |
| KR20040014550A (ko) | 2004-02-14 |
| JPWO2002100875A1 (ja) | 2004-09-24 |
| US20040149200A1 (en) | 2004-08-05 |
| JP4347042B2 (ja) | 2009-10-21 |
| EP1405856A1 (en) | 2004-04-07 |
| EP1405856B1 (en) | 2018-09-26 |
| CN100509830C (zh) | 2009-07-08 |
| CA2449736A1 (en) | 2002-12-19 |
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