JP2003093091A5 - - Google Patents
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- Publication number
- JP2003093091A5 JP2003093091A5 JP2002208987A JP2002208987A JP2003093091A5 JP 2003093091 A5 JP2003093091 A5 JP 2003093091A5 JP 2002208987 A JP2002208987 A JP 2002208987A JP 2002208987 A JP2002208987 A JP 2002208987A JP 2003093091 A5 JP2003093091 A5 JP 2003093091A5
- Authority
- JP
- Japan
- Prior art keywords
- cmp
- neuac
- synthetase
- glcnac
- epimerase
- 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
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 102000003960 Ligases Human genes 0.000 claims description 32
- 108090000364 Ligases Proteins 0.000 claims description 32
- 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 19
- 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 18
- 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 18
- 102000048245 N-acetylneuraminate lyases Human genes 0.000 claims description 16
- 108700023220 N-acetylneuraminate lyases Proteins 0.000 claims description 16
- 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 15
- 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 15
- 230000000694 effects Effects 0.000 claims description 13
- 210000004027 cell Anatomy 0.000 claims description 12
- 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 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- 210000005253 yeast cell Anatomy 0.000 claims description 6
- BRGMHAYQAZFZDJ-PVFLNQBWSA-N N-Acetylglucosamine 6-phosphate Chemical compound CC(=O)N[C@H]1[C@@H](O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O BRGMHAYQAZFZDJ-PVFLNQBWSA-N 0.000 claims description 5
- 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 5
- 108010081778 N-acylneuraminate cytidylyltransferase Proteins 0.000 claims description 5
- 229950006780 n-acetylglucosamine Drugs 0.000 claims description 5
- 229940107700 pyruvic acid Drugs 0.000 claims description 4
- -1 yeast cells Chemical compound 0.000 claims description 3
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 2
- 229940076788 pyruvate Drugs 0.000 claims description 2
- 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 claims 12
- 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 claims 4
- 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 3
- 229940060155 neuac Drugs 0.000 description 10
- 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 10
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 10
- 239000013612 plasmid Substances 0.000 description 8
- 108020004414 DNA Proteins 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 6
- 241000588724 Escherichia coli Species 0.000 description 6
- 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 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- 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 6
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 6
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 6
- 239000008103 glucose Substances 0.000 description 6
- 101150019075 neuA gene Proteins 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 229940054269 sodium pyruvate Drugs 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 4
- 229960000723 ampicillin Drugs 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- DTBNBXWJWCWCIK-UHFFFAOYSA-K phosphonatoenolpyruvate Chemical compound [O-]C(=O)C(=C)OP([O-])([O-])=O DTBNBXWJWCWCIK-UHFFFAOYSA-K 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 description 3
- 230000000813 microbial effect Effects 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 108091008146 restriction endonucleases Proteins 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 238000000246 agarose gel electrophoresis Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 101150041757 cmk gene Proteins 0.000 description 2
- 230000004186 co-expression Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 206010022000 influenza Diseases 0.000 description 2
- BPHPUYQFMNQIOC-NXRLNHOXSA-N isopropyl beta-D-thiogalactopyranoside Chemical compound CC(C)S[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O BPHPUYQFMNQIOC-NXRLNHOXSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000008057 potassium phosphate buffer Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 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 1
- 241000202785 Calyptronoma Species 0.000 description 1
- 101100245749 Campylobacter jejuni subsp. jejuni serotype O:23/36 (strain 81-176) pseF gene Proteins 0.000 description 1
- 102000012410 DNA Ligases Human genes 0.000 description 1
- 108010061982 DNA Ligases Proteins 0.000 description 1
- 230000004544 DNA amplification Effects 0.000 description 1
- 241001646716 Escherichia coli K-12 Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 101150026829 JUNB gene Proteins 0.000 description 1
- 101100126960 Mus musculus Cmpk1 gene Proteins 0.000 description 1
- AFPIKWGSISSARS-QOHRVMPQSA-N N-Acetylglucosamine phosphate Chemical compound CC(=O)N[C@@]12OP3(=O)O[C@]1(O)O[C@H](CO)[C@@H](O)[C@@]2(O)O3 AFPIKWGSISSARS-QOHRVMPQSA-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
- 108010035265 N-acetylneuraminate synthase Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 108020004511 Recombinant DNA Proteins 0.000 description 1
- 102100029954 Sialic acid synthase Human genes 0.000 description 1
- KBGAYAKRZNYFFG-BOHATCBPSA-N aceneuramic acid Chemical compound OC(=O)C(=O)C[C@H](O)[C@@H](NC(=O)C)[C@@H](O)[C@H](O)[C@H](O)CO KBGAYAKRZNYFFG-BOHATCBPSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- QDSLHWJDSQGPEE-WCTZXXKLSA-N aldehydo-N-acetyl-D-mannosamine 6-phosphate Chemical compound CC(=O)N[C@H](C=O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O QDSLHWJDSQGPEE-WCTZXXKLSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000013611 chromosomal DNA Substances 0.000 description 1
- 238000010367 cloning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000013613 expression plasmid Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- IBONACLSSOLHFU-KEWYIRBNSA-N n-[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]acetamide Chemical compound CC(=O)NC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O IBONACLSSOLHFU-KEWYIRBNSA-N 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229930029653 phosphoenolpyruvate Natural products 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002208987A JP3833584B2 (ja) | 2001-07-19 | 2002-07-18 | Ｃｍｐ−ｎ−アセチルノイラミン酸の製造法 |
| EP03700563A EP1541693A4 (en) | 2002-07-18 | 2003-01-15 | PROCESSES FOR PRODUCING CMP-N-ACETYLNEURAMINIC ACID |
| AU2003201882A AU2003201882A1 (en) | 2002-07-18 | 2003-01-15 | Processes for producing cmp-n-acetylneuraminic acid |
| CA002492838A CA2492838A1 (en) | 2002-07-18 | 2003-01-15 | Process for producing cmp-n-acetylneuraminic acid |
| KR1020057000945A KR100922085B1 (ko) | 2002-07-18 | 2003-01-15 | Ｃｍｐ-ｎ-아세틸뉴라민산의 제조 방법 |
| PCT/JP2003/000258 WO2004009830A1 (ja) | 2002-07-18 | 2003-01-15 | Cmp-n-アセチルノイラミン酸の製造法 |
| JP2004522712A JPWO2004009830A1 (ja) | 2002-07-18 | 2003-01-15 | Ｃｍｐ−ｎ−アセチルノイラミン酸の製造法 |
| CNB038170701A CN1301330C (zh) | 2002-07-18 | 2003-01-15 | Cmp－n－乙酰神经氨酸的制造方法 |
| CNB2006101003873A CN100413974C (zh) | 2002-07-18 | 2003-01-15 | Cmp-n-乙酰神经氨酸的制造方法 |
| US10/521,576 US7955825B2 (en) | 2002-07-18 | 2003-01-15 | Process for producing CMP-N-acetylneuraminic acid |
| US13/049,381 US20110207179A1 (en) | 2002-07-18 | 2011-03-16 | Process for producing cmp-n-acetylneuraminic acid |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001219242 | 2001-07-19 | ||
| JP2001-219242 | 2001-07-19 | ||
| JP2002208987A JP3833584B2 (ja) | 2001-07-19 | 2002-07-18 | Ｃｍｐ−ｎ−アセチルノイラミン酸の製造法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003093091A JP2003093091A (ja) | 2003-04-02 |
| JP2003093091A5 true JP2003093091A5 (enExample) | 2005-03-10 |
| JP3833584B2 JP3833584B2 (ja) | 2006-10-11 |
Family
ID=26618982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002208987A Expired - Fee Related JP3833584B2 (ja) | 2001-07-19 | 2002-07-18 | Ｃｍｐ−ｎ−アセチルノイラミン酸の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3833584B2 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7955825B2 (en) | 2002-07-18 | 2011-06-07 | Yamasa Corporation | Process for producing CMP-N-acetylneuraminic acid |
| JP5140242B2 (ja) | 2003-09-26 | 2013-02-06 | ヤマサ醤油株式会社 | Ｃｍｐ−ｎ−アセチルノイラミン酸の製造法 |
| JP2006271372A (ja) * | 2005-03-01 | 2006-10-12 | Yamasa Shoyu Co Ltd | 糖鎖の製造法 |
| JP5079272B2 (ja) * | 2006-06-30 | 2012-11-21 | 協和発酵バイオ株式会社 | シチジン‐５´‐一リン酸‐ｎ‐アセチルノイラミン酸およびｎ‐アセチルノイラミン酸含有糖質の製造法 |
| JP4901447B2 (ja) * | 2006-12-18 | 2012-03-21 | ヤマサ醤油株式会社 | Ｃｍｐ−デアミノノイラミン酸の製造法 |
| CN114014896B (zh) * | 2021-10-09 | 2023-12-05 | 中国科学院合肥物质科学研究院 | 一种高纯度3`-唾液酸乳糖的分离纯化方法 |
-
2002
- 2002-07-18 JP JP2002208987A patent/JP3833584B2/ja not_active Expired - Fee Related
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