JP2016519952A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016519952A5 JP2016519952A5 JP2016516451A JP2016516451A JP2016519952A5 JP 2016519952 A5 JP2016519952 A5 JP 2016519952A5 JP 2016516451 A JP2016516451 A JP 2016516451A JP 2016516451 A JP2016516451 A JP 2016516451A JP 2016519952 A5 JP2016519952 A5 JP 2016519952A5
- Authority
- JP
- Japan
- Prior art keywords
- amino acid
- sialyltransferase
- seq
- acid sequence
- cmp
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- IERHLVCPSMICTF-UHFFFAOYSA-N cytidine monophosphate Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(COP(O)(O)=O)O1 IERHLVCPSMICTF-UHFFFAOYSA-N 0.000 claims description 36
- IERHLVCPSMICTF-ZAKLUEHWSA-N cytidine-5'-monophosphate Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](COP(O)(O)=O)O1 IERHLVCPSMICTF-ZAKLUEHWSA-N 0.000 claims description 36
- 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 22
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 claims description 22
- 108010092060 Acetate kinase Proteins 0.000 claims description 21
- OVRNDRQMDRJTHS-RTRLPJTCSA-N N-acetyl-D-glucosamine Chemical compound CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-RTRLPJTCSA-N 0.000 claims description 11
- 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 11
- 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 11
- 229950006780 n-acetylglucosamine Drugs 0.000 claims description 11
- 229940054269 sodium pyruvate Drugs 0.000 claims description 11
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 10
- LIPOUNRJVLNBCD-UHFFFAOYSA-N acetyl dihydrogen phosphate Chemical compound CC(=O)OP(O)(O)=O LIPOUNRJVLNBCD-UHFFFAOYSA-N 0.000 claims description 10
- 229940076788 pyruvate Drugs 0.000 claims description 10
- 108091000080 Phosphotransferase Proteins 0.000 claims description 9
- 102000020233 phosphotransferase Human genes 0.000 claims description 9
- OIZGSVFYNBZVIK-FHHHURIISA-N 3'-sialyllactose Chemical compound O1[C@@H]([C@H](O)[C@H](O)CO)[C@H](NC(=O)C)[C@@H](O)C[C@@]1(C(O)=O)O[C@@H]1[C@@H](O)[C@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)O[C@H](CO)[C@@H]1O OIZGSVFYNBZVIK-FHHHURIISA-N 0.000 claims description 8
- 108010081778 N-acylneuraminate cytidylyltransferase Proteins 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 102000003838 Sialyltransferases Human genes 0.000 claims description 6
- 108090000141 Sialyltransferases Proteins 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical class CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 claims description 5
- -1 sialic acid derivative compounds Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 102000001390 Fructose-Bisphosphate Aldolase Human genes 0.000 claims description 3
- 108010068561 Fructose-Bisphosphate Aldolase Proteins 0.000 claims description 3
- 102000004357 Transferases Human genes 0.000 claims description 3
- 108090000992 Transferases Proteins 0.000 claims description 3
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical group OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 3
- 229930182830 galactose Natural products 0.000 claims description 3
- 229930003935 flavonoid Natural products 0.000 claims description 2
- 150000002215 flavonoids Chemical class 0.000 claims description 2
- 235000017173 flavonoids Nutrition 0.000 claims description 2
- 239000002773 nucleotide Substances 0.000 claims description 2
- 125000003729 nucleotide group Chemical group 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 235000011178 triphosphate Nutrition 0.000 claims description 2
- 239000001226 triphosphate Substances 0.000 claims description 2
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003275 alpha amino acid group Chemical group 0.000 claims 8
- 150000001413 amino acids Chemical class 0.000 claims 3
- 238000006467 substitution reaction Methods 0.000 claims 3
- 241000566113 Branta sandvicensis Species 0.000 claims 1
- 102100031349 N-acylneuraminate cytidylyltransferase Human genes 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 229940088710 antibiotic agent Drugs 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 229940125721 immunosuppressive agent Drugs 0.000 claims 1
- 239000003018 immunosuppressive agent Substances 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 claims 1
- 150000002772 monosaccharides Chemical class 0.000 claims 1
- 229920001542 oligosaccharide Polymers 0.000 claims 1
- 150000002482 oligosaccharides Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 8
- 239000000872 buffer Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 102000048245 N-acetylneuraminate lyases Human genes 0.000 description 7
- 108700023220 N-acetylneuraminate lyases Proteins 0.000 description 7
- 239000002253 acid Substances 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- TXCIAUNLDRJGJZ-UHFFFAOYSA-N CMP-N-acetyl neuraminic acid Natural products O1C(C(O)C(O)CO)C(NC(=O)C)C(O)CC1(C(O)=O)OP(O)(=O)OCC1C(O)C(O)C(N2C(N=C(N)C=C2)=O)O1 TXCIAUNLDRJGJZ-UHFFFAOYSA-N 0.000 description 3
- TXCIAUNLDRJGJZ-BILDWYJOSA-N CMP-N-acetyl-beta-neuraminic acid Chemical compound O1[C@@H]([C@H](O)[C@H](O)CO)[C@H](NC(=O)C)[C@@H](O)C[C@]1(C(O)=O)OP(O)(=O)OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C(N=C(N)C=C2)=O)O1 TXCIAUNLDRJGJZ-BILDWYJOSA-N 0.000 description 3
- 238000012423 maintenance Methods 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 2
- 102000003960 Ligases Human genes 0.000 description 2
- 108090000364 Ligases Proteins 0.000 description 2
- 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 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 239000008101 lactose Substances 0.000 description 2
- 229940060155 neuac Drugs 0.000 description 2
- 101150108487 pst2 gene Proteins 0.000 description 2
- 241000511343 Chondrostoma nasus Species 0.000 description 1
- 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 description 1
- 102000002307 N-acylglucosamine 2-epimerase Human genes 0.000 description 1
- 108060005182 N-acylglucosamine 2-epimerase Proteins 0.000 description 1
- 101710163270 Nuclease Proteins 0.000 description 1
- 229930012538 Paclitaxel Natural products 0.000 description 1
- 102000001253 Protein Kinase Human genes 0.000 description 1
- 108010059993 Vancomycin Proteins 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002597 lactoses Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CERZMXAJYMMUDR-UHFFFAOYSA-N neuraminic acid Natural products NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO CERZMXAJYMMUDR-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960001967 tacrolimus Drugs 0.000 description 1
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020130062733A KR101525230B1 (ko) | 2013-05-31 | 2013-05-31 | 시알산 유도체의 제조방법 |
| KR10-2013-0062733 | 2013-05-31 | ||
| PCT/KR2014/004823 WO2014193183A1 (ko) | 2013-05-31 | 2014-05-30 | 시알산 유도체의 제조방법 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016519952A JP2016519952A (ja) | 2016-07-11 |
| JP2016519952A5 true JP2016519952A5 (enExample) | 2016-08-18 |
| JP6129412B2 JP6129412B2 (ja) | 2017-05-17 |
Family
ID=51989130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016516451A Active JP6129412B2 (ja) | 2013-05-31 | 2014-05-30 | シアル酸誘導体の製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9637768B2 (enExample) |
| EP (1) | EP3009516A4 (enExample) |
| JP (1) | JP6129412B2 (enExample) |
| KR (1) | KR101525230B1 (enExample) |
| CN (1) | CN105473728A (enExample) |
| WO (1) | WO2014193183A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2708759T3 (es) | 2013-05-13 | 2019-04-11 | Momenta Pharmaceuticals Inc | Procedimientos para el tratamiento de la neurodegeneración |
| WO2015057622A1 (en) | 2013-10-16 | 2015-04-23 | Momenta Pharmaceuticals, Inc. | Sialylated glycoproteins |
| WO2016045704A1 (en) | 2014-09-23 | 2016-03-31 | Huawei Technologies Co.,Ltd | Transmitter, receiver and methods for transmitting/ receiving synchronisation signals |
| CN106520864A (zh) * | 2016-09-28 | 2017-03-22 | 南京农业大学 | 一种酶法合成唾液酸类似物的方法及其应用 |
| WO2019020707A1 (en) * | 2017-07-26 | 2019-01-31 | Jennewein Biotechnologie Gmbh | SIALYL-TRANSFERASES AND THEIR USE IN THE PRODUCTION OF SIALYLATED OLIGOSACCHARIDES |
| JP6559763B2 (ja) * | 2017-12-14 | 2019-08-14 | ホアウェイ・テクノロジーズ・カンパニー・リミテッド | 送信機、受信機、および同期信号を送信／受信するための方法 |
| AU2018386217A1 (en) * | 2017-12-15 | 2020-07-02 | Glycosyn LLC | Sialyltransferases and uses thereof |
| CN110227164B (zh) | 2018-03-06 | 2021-11-23 | 江苏吉贝尔药业股份有限公司 | 含酮羰基的疏水性抗肿瘤药物及其缀合物、含有缀合物的纳米制剂及其制备方法及应用 |
| CN108409810A (zh) * | 2018-03-30 | 2018-08-17 | 广州中医药大学(广州中医药研究院) | 紫杉烷类化合物糖基化衍生物及其制备方法和应用 |
| GB2573539A (en) | 2018-05-09 | 2019-11-13 | Mjn Us Holdings Llc | Wellbeing supplement for postpartum maternal nutrition |
| US20220089631A1 (en) * | 2018-08-23 | 2022-03-24 | Genechem Inc. | Compound comprising multivalent sialyloligosaccharide residues, and composition for preventing or treating viral infection diseases, containing same as active ingredient |
| CN111248289B (zh) * | 2018-11-30 | 2023-04-07 | 内蒙古伊利实业集团股份有限公司 | 一种组合物、其制备方法及用途 |
| KR102245274B1 (ko) | 2019-01-28 | 2021-04-27 | 재단법인 지능형 바이오 시스템 설계 및 합성 연구단 | 최소 유전체를 갖는 신규 미생물 및 이의 제조 방법 |
| CN110396532A (zh) * | 2019-08-23 | 2019-11-01 | 中国科学院合肥物质科学研究院 | 一种制备唾液酸乳糖的方法 |
| CN111233949A (zh) * | 2020-02-10 | 2020-06-05 | 天津科技大学 | 一种神经节苷脂gm3和/或其类似物、合成方法和应用 |
| CN111249444B (zh) * | 2020-03-10 | 2023-04-07 | 西北大学 | 一种用于抑制白色念珠菌的制剂 |
| CN111394292B (zh) * | 2020-03-30 | 2022-08-09 | 江南大学 | 一种多途径复合产神经氨酸枯草芽孢杆菌及其应用 |
| EP3892731A1 (en) | 2020-04-08 | 2021-10-13 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Enzymatic method for preparation of cmp-neu5ac |
| KR20230099676A (ko) * | 2021-12-27 | 2023-07-04 | 주식회사 진켐 | 시알릴락토스를 이용한 혈뇌장벽 투과용 약물 전달체 |
| CN114736884B (zh) * | 2022-05-11 | 2023-10-20 | 中国科学院合肥物质科学研究院 | 一种胞苷单磷酸激酶突变体及其基因和应用 |
| CN119351382A (zh) * | 2023-11-28 | 2025-01-24 | 深圳瑞德林生物技术有限公司 | 酶组合物及其在制备唾液酸乳糖中的应用 |
| CN119662773A (zh) * | 2024-11-12 | 2025-03-21 | 深圳瑞德林生物技术有限公司 | 高通量平板筛选3-唾液酸转移酶突变体的试剂和方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3937891A1 (de) | 1989-11-15 | 1991-05-16 | Forschungszentrum Juelich Gmbh | Enzymatisches verfahren zur herstellung von n-acetylneuraminsaeure |
| JP3131655B2 (ja) | 1992-02-03 | 2001-02-05 | マルキン忠勇株式会社 | Ｎ−アセチルノイラミン酸の製造法 |
| WO1995026399A1 (fr) | 1994-03-25 | 1995-10-05 | Marukin Shoyu Co., Ltd. | Epimerase |
| ATE222294T1 (de) * | 1995-04-11 | 2002-08-15 | Neose Technologies Inc | Verbesserte verfahren zur enzymatischen synthese von oligosacchariden |
| JP3944866B2 (ja) | 1996-06-18 | 2007-07-18 | マルキンバイオ株式会社 | Ｎ−アセチルノイラミン酸シンターゼ、及びこれを用いるｎ−アセチルノイラミン酸の製造方法 |
| US6846656B1 (en) | 1999-08-30 | 2005-01-25 | Kyowa Hakko Kogyo Co., Ltd. | Process for producing N-acetylneuraminic acid |
| CN1301330C (zh) | 2002-07-18 | 2007-02-21 | 雅玛山酱油株式会社 | Cmp－n－乙酰神经氨酸的制造方法 |
| KR100888513B1 (ko) * | 2006-12-15 | 2009-03-12 | 주식회사 진켐 | 신규 ｎ―아세틸글루코사민―２―에피머라아제 및 이를이용한 ｃｍｐ―ｎ―아세틸뉴라민산의 제조방법 |
| CN103108956A (zh) * | 2010-07-16 | 2013-05-15 | 格力康公司 | 新型唾液酸寡糖衍生物的合成 |
-
2013
- 2013-05-31 KR KR1020130062733A patent/KR101525230B1/ko active Active
-
2014
- 2014-05-30 CN CN201480042946.2A patent/CN105473728A/zh active Pending
- 2014-05-30 WO PCT/KR2014/004823 patent/WO2014193183A1/ko not_active Ceased
- 2014-05-30 EP EP14803659.3A patent/EP3009516A4/en not_active Withdrawn
- 2014-05-30 JP JP2016516451A patent/JP6129412B2/ja active Active
- 2014-05-30 US US14/894,757 patent/US9637768B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2016519952A5 (enExample) | ||
| JP6129412B2 (ja) | シアル酸誘導体の製造方法 | |
| TWI567200B (zh) | 寡醣之大規模酵素合成 | |
| Ichikawa et al. | Enzyme-catalyzed oligosaccharide synthesis | |
| US20160289721A1 (en) | DIVERSIFICATION OF HUMAN MILK OLIGOSACCHARIDES (HMOs) OR PRECURSORS THEREOF | |
| WO1994025615A1 (en) | USE OF TRANS-SIALIDASE AND SIALYLTRANSFERASE FOR SYNTHESIS OF SIALYLα2→3βGALACTOSIDES | |
| CN103443113A (zh) | 新型含岩藻糖的糖类衍生物的合成 | |
| Chien et al. | Sequential one-pot enzymatic synthesis of oligo-N-acetyllactosamine and its multi-sialylated extensions | |
| US5770407A (en) | Process for preparing nucleotide inhibitors of glycosyltransferases | |
| Yan et al. | Chemoenzymatic synthesis of mono-and di-fluorinated Thomsen–Friedenreich (T) antigens and their sialylated derivatives | |
| Li et al. | Efficient chemoenzymatic synthesis of novel galacto-N-biose derivatives and their sialylated forms | |
| WO2024040628A1 (zh) | 酶催化合成嘌呤核苷的方法及组合物 | |
| CN104561195A (zh) | 一种尿苷二磷酸葡萄糖的制备方法 | |
| CN106811493A (zh) | 葡萄糖1-磷酸的制备方法 | |
| JP4601060B2 (ja) | アジド化アミノ糖ヌクレオチド及びその応用 | |
| WO2007144168A1 (en) | Enzymatic process for preparation of 5'-monophosphate-nucleotides | |
| CN116814720B (zh) | 一种巯基修饰寡糖的合成方法 | |
| KR20250151691A (ko) | 시알릴올리고당의 제조방법 | |
| JP4910091B2 (ja) | ４位ハロゲン化ガラクトース含有糖鎖及びその応用 | |
| JP2006271372A (ja) | 糖鎖の製造法 | |
| CN121204190A (zh) | 一种n-乙酰葡萄糖胺6号位磺基化人乳寡糖的合成方法 | |
| CN119351496A (zh) | 一种酶法合成血型抗原nor1五糖的方法 | |
| CN109072272A (zh) | 一种酶法制备磷酸氟达拉滨的方法 | |
| CN120989038A (zh) | 一种用于合成功能聚糖的多酶催化系统及方法 | |
| WO2023115798A1 (zh) | 一种由UDP-GlcNAc合成稀有糖核苷酸的方法 |