CN112225770A - 一种烟酰胺单核苷酸(nmn)的化学合成方法 - Google Patents
一种烟酰胺单核苷酸(nmn)的化学合成方法 Download PDFInfo
- Publication number
- CN112225770A CN112225770A CN202011115269.6A CN202011115269A CN112225770A CN 112225770 A CN112225770 A CN 112225770A CN 202011115269 A CN202011115269 A CN 202011115269A CN 112225770 A CN112225770 A CN 112225770A
- Authority
- CN
- China
- Prior art keywords
- ethyl acetate
- beta
- nicotinamide mononucleotide
- nicotinamide
- reaction
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 14
- DAYLJWODMCOQEW-TURQNECASA-O NMN(+) Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP(O)(O)=O)O2)O)=C1 DAYLJWODMCOQEW-TURQNECASA-O 0.000 title claims abstract 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 72
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims abstract description 20
- FZAQROFXYZPAKI-UHFFFAOYSA-N anthracene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC3=CC(S(=O)(=O)Cl)=CC=C3C=C21 FZAQROFXYZPAKI-UHFFFAOYSA-N 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000003756 stirring Methods 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 8
- 239000007787 solid Substances 0.000 claims abstract description 8
- 239000007864 aqueous solution Substances 0.000 claims abstract description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000001514 detection method Methods 0.000 claims abstract 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 claims abstract description 4
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 238000011033 desalting Methods 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 4
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 4
- 239000011618 nicotinamide riboside Substances 0.000 claims abstract description 4
- 238000010791 quenching Methods 0.000 claims abstract description 4
- 230000000171 quenching effect Effects 0.000 claims abstract description 4
- 238000005070 sampling Methods 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 15
- 239000011259 mixed solution Substances 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 2
- 238000007598 dipping method Methods 0.000 claims 1
- 238000004108 freeze drying Methods 0.000 abstract description 2
- 238000012544 monitoring process Methods 0.000 abstract description 2
- DAYLJWODMCOQEW-TURQNECASA-N NMN zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP(O)([O-])=O)O2)O)=C1 DAYLJWODMCOQEW-TURQNECASA-N 0.000 description 30
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 description 16
- 229950006238 nadide Drugs 0.000 description 14
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000001413 cellular effect Effects 0.000 description 4
- 239000005515 coenzyme Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000003834 intracellular effect Effects 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 241000282412 Homo Species 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- 108050002485 Sirtuin Proteins 0.000 description 2
- 230000003712 anti-aging effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 229940101270 nicotinamide adenine dinucleotide (nad) Drugs 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- -1 248.73mmol Chemical compound 0.000 description 1
- 108010013043 Acetylesterase Proteins 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 102000011724 DNA Repair Enzymes Human genes 0.000 description 1
- 108010076525 DNA Repair Enzymes Proteins 0.000 description 1
- 230000005778 DNA damage Effects 0.000 description 1
- 231100000277 DNA damage Toxicity 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 102000003960 Ligases Human genes 0.000 description 1
- 108090000364 Ligases Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- BAWFJGJZGIEFAR-NNYOXOHSSA-O NAD(+) Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-O 0.000 description 1
- 102100033223 Nicotinamide phosphoribosyltransferase Human genes 0.000 description 1
- 108010064862 Nicotinamide phosphoribosyltransferase Proteins 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 102000011990 Sirtuin Human genes 0.000 description 1
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000037149 energy metabolism Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000009758 senescence Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000004102 tricarboxylic acid cycle Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/048—Pyridine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
Abstract
本发明公开了一种烟酰胺单核苷酸(NMN)的化学合成方法,包括步骤:S1,依次将β‑烟酰胺核糖和四氢呋喃加入三颈反应瓶中,在冰浴中冷却至5℃,S2,然后缓慢添加氧氯化磷至5℃以下,滴加过程放热,S3,滴注完成,静置12小时,反应自然升温至室温,然后取样进行HPLC检测,高效液相色谱法监测β‑烟酰胺核糖反应完成后,停止反应,并将温度控制在0℃~5℃,S4,将液体缓慢倒入室温水中,对过量的氧氯化磷进行猝灭,反应析出的固体逐渐溶解,S5,然后加入乙酸乙酯,搅拌,除去乙酸乙酯层,在水层中加入醋酸和乙酸乙酯,搅拌,除去乙酸乙酯层,水层经离子交换树脂脱盐,得到β‑烟酰胺单核苷酸水溶液,S6,最后将β‑烟酰胺单核苷酸水溶液冻干,得到白色固体β‑烟酰胺单核苷酸。
Description
技术领域
本发明涉及一种生物化学领域,特别涉及一种烟酰胺单核苷酸(NMN)的化学合成方法。
技术背景
烟酰胺单核苷酸(NMN,cas号:1094-61-7)为烟酰胺腺嘌呤二核苷酸(NAD+)的合成中间体。近年来,明确了NMN通过向NAD+的转变来控制长寿基因“Sirtuin”的活性,如果将NMN施与至小鼠则显示抗衰老作用。进一步,还报道了NMN对于糖尿病、阿尔茨海默症、心力衰竭等疾病的预防、症状的改善有效果。期待这样的NMN作为功能性食品、药品、化妆品等的成分的用途,以生产性的提高为目标,高效的制造方法的研究开发正在进行着。
烟酰胺单核苷酸(NMN)在人体细胞能量生成中扮演重要角色,它参与细胞内NAD(烟酰胺腺嘌呤二核苷酸,细胞能量转化的重要辅酶)的合成。烟酰胺单核苷酸(NMN),人体内原本该物质存在,但随着年龄的增长而减少。NMN在人体细胞能量生成中扮演重要角色,它参与细胞内烟酰胺腺嘌呤二核苷酸(NAD)的合成,而NAD是细胞能量转化的重要辅酶。
在哺乳动物体内,β-烟酰胺单核苷酸由烟酰胺(Nicotinamide,Nam)在Nampt(体内一种蛋白酶)的催化下生成,随后烟酰胺单核苷酸在烟酰胺单核苷酸腺苷转移酶的催化下生成NAD+。烟酰胺单核苷酸是补充NAD+直接的方式。烟酰胺单核苷酸正是通过显著提升细胞内DNA损伤的修复能力,最Chemicalbook终实现了逆转衰老的效果。烟酰胺单核苷酸会转化成体内能量代谢必不可少的“烟酰胺腺嘌呤二核苷酸(NAD)”物质。在小鼠试验中,证实烟酰胺单核苷酸可激活体内一种叫做乙酰化酶的基因,以此发挥延年益寿和治疗糖尿病等效果。NAD是人体原本可以生成的物质,研究证实体内的NAD含量会随着年龄的增加而减少。
β-烟酰胺单核苷酸是人体内长寿蛋白的辅因子NAD+的前体物质。NAD+是三羧酸循环的重要辅酶,促进糖、脂肪、氨基酸的代谢,参与能量的合成;NAD+又是辅酶I消耗酶的唯一底物(DNA修复酶PARP的唯一底物、长寿蛋白Sirtuins的Chemicalbook唯一底物、环ADP核糖合成酶CD38/157的唯一底物)。NAD+参与人体新陈代谢的方方面面,是关键性的辅酶,缺了NAD+,新陈代谢就不行了,老年人缺少了NAD+,于是各种大大小小的毛病就来了,通过额外补充NAD+,可以全面抗衰老。
发明内容
本发明的主要目的在于提供了一种烟酰胺单核苷酸(NMN)的化学合成方法,可以有效且准确的合成烟酰胺单核苷酸(NMN),且生产成本较低。
为实现上述目的,本发明采取的技术方案为:
一种烟酰胺单核苷酸(NMN)的化学合成方法,包括步骤:
S1,依次将β-烟酰胺核糖,即化学物(A)和四氢呋喃加入三颈反应瓶中,在冰浴中冷却至5℃;
S2,然后缓慢添加氧氯化磷至5℃以下,滴加过程放热;
S3,滴注完成,静置12小时,反应自然升温至室温,然后取样进行HPLC检测,高效液相色谱法监测β-烟酰胺核糖反应完成后,停止反应;
S4,将混合反应后的液体缓慢倒入室温水中,对过量的氧氯化磷进行猝灭,反应析出的固体逐渐溶解;
S5,然后加入乙酸乙酯,搅拌,除去乙酸乙酯层,水层经离子交换树脂脱盐,得到β-烟酰胺单核苷酸水溶液,即化学物(B);
S6,最后将β-烟酰胺单核苷酸水溶液冻干,得到白色固体β-烟酰胺单核苷酸。
进一步的,所述步骤S1~S5中的各物质的比例为:β-烟酰胺核糖2.1-2.3%,四氢呋喃10.6-10.7%,氧氯化磷2.0-2.1%,室温水53.2-53.3%,乙酸乙酯31.9%-32.0%。
进一步的,所述S5中先后加入两次乙酸乙酯,第一次加入总物质比例的21.2-21.3%的乙酸乙酯,待搅拌,除去乙酸乙酯层后,再次加入醋酸和乙酸乙酯的混合液,该混合液沾总物质的10.6-10.7%,并进行搅拌和除去乙酸乙酯层。
更进一步的,所述步骤S3中停止反应的混合液体,需要将温度控制在0-5℃。
与现有技术相比,本发明的有益效果为:
本发明中的方法操作简单,可以有效且准确的合成烟酰胺单核苷酸(NMN),且生产成本较低。
附图说明
图1为本发明的化学合成路线图。
具体实施方式
下面结合实施例对本发明作详细阐述,以使本发明的优点和特征能更易于被本领域技术人员理解,从而对本发明的保护范围作出更为清楚明确的界定。
实施例:依次将β-烟酰胺核糖40g,即465.82mmol(即化合物A)和四氢呋喃200ml加入三颈反应瓶中,在冰浴中冷却至5℃,然后缓慢添加氧氯化磷38.14g,即248.73mmol,滴加过程混合液体放热,使混合液体温度降至5以下,滴注完成,反应自然升温至室温,静置12小时,然后取样进行HPLC检测;
检测高效液相色谱法监测β-烟酰胺核糖反应完成后,停止反应,并将混合液体的温度控制在0℃~5℃。将液体缓慢倒入1L室温水中,对过量的氧氯化磷进行猝灭,反应析出的固体逐渐溶解,加入后加入乙酸乙酯400ml,搅拌,除去乙酸乙酯层,再次在水层中加入醋酸和乙酸乙酯混合液200ml,搅拌,除去乙酸乙酯层,水层经离子交换树脂脱盐,得到β-烟酰胺单核苷酸(即化合物B)水溶液,最后将β-烟酰胺单核苷酸水溶液冻干,得到白色固体β-烟酰胺单核苷酸31.4g,收率56%,。
以上所述仅为本发明的较佳实施方式,本发明的保护范围并不以上述实施方式为限,但凡本领域普通技术人员根据本发明所揭示内容所作的等效修饰或变化,皆应纳入权利要求书中记载的保护范围内。
Claims (4)
1.一种烟酰胺单核苷酸(NMN)的化学合成方法,包括步骤:
S1,依次将β-烟酰胺核糖,即化学物(A)和四氢呋喃加入三颈反应瓶中,在冰浴中冷却至5℃;
S2,然后缓慢添加氧氯化磷至5℃以下,滴加过程放热;
S3,滴注完成,静置12小时,反应自然升温至室温,然后取样进行HPLC检测,高效液相色谱法监测β-烟酰胺核糖反应完成后,停止反应;
S4,将混合反应后的液体缓慢倒入室温水中,对过量的氧氯化磷进行猝灭,反应析出的固体逐渐溶解;
S5,然后加入乙酸乙酯,搅拌,除去乙酸乙酯层,水层经离子交换树脂脱盐,得到β-烟酰胺单核苷酸水溶液,即化学物(B);
S6,最后将β-烟酰胺单核苷酸水溶液冻干,得到白色固体β-烟酰胺单核苷酸。
2.根据权利要求1所述的一种烟酰胺单核苷酸(NMN)的化学合成方法,其特征在于:所述步骤S1~S5中的各物质的比例为:β-烟酰胺核糖2.1-2.3%,四氢呋喃10.6-10.7%,氧氯化磷2.0-2.1%,室温水53.2-53.3%,乙酸乙酯31.9%-32.0%。
3.根据权利要求1所述的一种烟酰胺单核苷酸(NMN)的化学合成方法,其特征在于:所述S5中先后加入两次乙酸乙酯,第一次加入总物质比例的21.2-21.3%的乙酸乙酯,待搅拌,除去乙酸乙酯层后,再次加入醋酸和乙酸乙酯的混合液,该混合液沾总物质的10.6-10.7%,并进行搅拌和除去乙酸乙酯层。
4.根据权利要求1所述的一种烟酰胺单核苷酸(NMN)的化学合成方法,其特征在于:所述步骤S3中停止反应的混合液体,需要将温度控制在0-5℃。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202011115269.6A CN112225770A (zh) | 2020-10-19 | 2020-10-19 | 一种烟酰胺单核苷酸(nmn)的化学合成方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202011115269.6A CN112225770A (zh) | 2020-10-19 | 2020-10-19 | 一种烟酰胺单核苷酸(nmn)的化学合成方法 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN112225770A true CN112225770A (zh) | 2021-01-15 |
Family
ID=74117864
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202011115269.6A Pending CN112225770A (zh) | 2020-10-19 | 2020-10-19 | 一种烟酰胺单核苷酸(nmn)的化学合成方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN112225770A (zh) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110483601A (zh) * | 2019-08-12 | 2019-11-22 | 上海龙翔生物医药开发有限公司 | 制备β-烟酸胺单核苷酸的方法及其应用 |
CN111548383A (zh) * | 2020-06-11 | 2020-08-18 | 湖南和泰康瑞生物技术有限公司 | 一种β-烟酰胺单核苷酸的工艺制备方法 |
-
2020
- 2020-10-19 CN CN202011115269.6A patent/CN112225770A/zh active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110483601A (zh) * | 2019-08-12 | 2019-11-22 | 上海龙翔生物医药开发有限公司 | 制备β-烟酸胺单核苷酸的方法及其应用 |
CN111548383A (zh) * | 2020-06-11 | 2020-08-18 | 湖南和泰康瑞生物技术有限公司 | 一种β-烟酰胺单核苷酸的工艺制备方法 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Rafikova et al. | Focus on early events: pathogenesis of pulmonary arterial hypertension development | |
Matthews et al. | Inhibition of pig liver methylenetetrahydrofolate reductase by dihydrofolate: some mechanistic and regulatory implications | |
Kalckar et al. | Galactosemia, a congenital defect in a nucleotide transferase: a preliminary report | |
CN110483601A (zh) | 制备β-烟酸胺单核苷酸的方法及其应用 | |
US8257758B2 (en) | Process for the extraction, purification and enzymatic modification of soy 7S globulin alpha' subunit for use as hypocholesterolemizing agent | |
CN101230373B (zh) | 一种s-腺苷蛋氨酸的制备方法 | |
WO2011110056A1 (zh) | 一种微生物生产环腺苷酸的方法 | |
Smellie et al. | The nucleic acid metabolism of animal cells in vitro: I. The incorporation of 14C-formate | |
CN116589533A (zh) | 南极磷虾小分子活性肽及其制备方法和应用 | |
CN112225770A (zh) | 一种烟酰胺单核苷酸(nmn)的化学合成方法 | |
Krungkrai et al. | Mitochondrial NADH dehydrogenase from Plasmodium falciparum and Plasmodium berghei | |
CN107254520A (zh) | 一种叶酸代谢相关基因的检测方法 | |
CN101468955A (zh) | 一种n-乙酰-l-谷氨酰胺的生产方法 | |
CN111378705B (zh) | 一种腺苷水解酶水解腺苷制备腺嘌呤和d-核糖的方法 | |
CN111088301B (zh) | 一种l型稀有己酮糖的制备方法 | |
Rogers | The components of Life: From nucleic acids to carbohydrates | |
JPWO2017199951A1 (ja) | 糖尿病予防効果を有する酵母エキス | |
Kumar et al. | Guanine deaminase in rat liver and mouse liver and brain | |
TWI327918B (zh) | ||
Wei et al. | Integrated transcriptomics, proteomics and metabolomics to identify biomarkers of astragaloside IV against cerebral ischemic injury in rats | |
Zhang et al. | Mechanism of extraordinary DNA digestion by pepsin | |
Yoshida et al. | Alterations of tetrahydrobiopterin biosynthesis and pteridine levels in mouse tissues during growth and aging | |
Kang et al. | An efficient cell-free protein synthesis system using periplasmic phosphatase-removed S30 extract | |
Cerecedo | The chemistry and metabolism of the nucleic acids, purines, and pyrimidines | |
WO2021134439A1 (zh) | 一种提高磷脂酶d转脂活性的方法以及用其生产磷脂酰丝氨酸的方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
RJ01 | Rejection of invention patent application after publication | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20210115 |