CAS: 554-01-8; 4-Amino-5-Methylpyrimidin-2(1H)-One

该化合物是一种由细胞素衍生的经修改的核子基地,其特点是将一组甲基物质添加到青糖环的碳5位置,在调节基因表达方面起着关键作用,是各种生物体,包括植物和哺乳动物的遗传机制的重要组成部分,通常见于DNA中,DNA有助于双螺旋的稳定性,并影响转录因素的结合.5-甲基基辛的存在会影响铬结构和基因的可获得性,从而影响细胞过程,例如分化和发育.在物理特性方面,5-甲基基锡因是一种白色的对非白晶状固体,在水和极有机溶剂中溶解,其化学配方是C5H6N2O,其分子重量约为126.11克/摩尔.该化合物对分子生物学和遗传学具有重大兴趣,特别是在DNA甲基化模式研究及其对健康和疾病的影响方面.

结构式图片

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

CAS号838-07-3 2 '-脱氧-5-甲基胞苷 | CAS号2140-61-6 5-甲基胞苷 | CAS号65-71-4 胸腺嘧啶 | CAS号54410-87-6 2-(Ethylthio)-5... | CAS号25902-89-0 2(1H)-Pyrimidin... | CAS号50-89-5 beta-胸苷 | CAS号7390-56-9 4-amino-5-methy... | CAS号6217-61-4 5-甲基嘧啶-2,4(1H,3... | CAS号13480-96-1 Pyrimidine,4-ch... | CAS号65-71-4 胸腺嘧啶 | CAS号69256-17-3 2'-氟-5-甲基阿拉伯糖基尿嘧啶 | CAS号160107-15-3 N4-Benzoyl-5-me... | CAS号116-09-6 羟基丙酮 | CAS号1123-95-1 5-羟甲基胞嘧啶 | CAS号32865-88-6 5-Methyl-N-(tri... | CAS号17634-60-5 2(1H)-Pyrimidin... | CAS号126354-30-1 N-(5-甲基-2-氧代-2,... | CAS号2140-61-6 5-甲基胞苷 | CAS号78636-53-0 2′-Deoxy-2′-flu...

合成工艺路线路线简述

  • 合成目标产物 5-Methylcytosine 主要起始原料 Thymine
  • (文献来源)合成步骤主要原料 Thymine
2-Ethylsulfanyl-5-Methyl-Pyrimidin-4-Ylamine 反应生成 5-甲基胞嘧啶
参考文献:Harkins; Johnson,Journal Of The American Chemical Society,1929,Vol. 51,P. 1241
标题:Harkins; Johnson,Journal Of The American Chemical Society,1929,Vol. 51,P. 1241

专利信息


专利号:US-9920084-B2
优先权日:2011-08-23
标题 :Ionic tags for synthesis of oligoribonucleotides
发明人:DAMHA MASAD J; HASSLER MATTHEW; CHAN TAK-HANG; NANDYALA MALLIKARJUNA REDDY; DONGA ROBERT ALEXANDER
权利人:DAMHA MASAD J; HASSLER MATTHEW; CHAN TAK HANG; NANDYALA MALLIKARJUNA REDDY; DONGA ROBERT ALEXANDER; THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING/MCGILL UNIV; HONG KONG POLYTECHNIC UNIV
摘要:The invention relates to the chemical synthesis of oligonucleotides, e.g., oligoribonucleotides. In another aspect, the invention relates to compounds of formula (II) processes for making these compounds, and the use thereof in the chemical synthesis of oligonucleotides, e.g., oligoribonucleotides. The invention also relates to methods of synthesis of oligomers, including but not limited to oligopeptides, oligosaccharides and oligonucleotides, particularly oligoribonucleotides and also oligodeoxyribonucleotides, in solution systems, and ionic tag linkers for use in methods provided herein.

专利号:US-9884885-B2
优先权日:2009-05-18
标题:Synthesis of labile base protected-modified deoxy and modified ribo nucleosides, corresponding phosphoramidites and supports and their use in high purity oligonucleotide synthesis
发明人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P
权利人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P; CHEMGENES CORP
摘要:This invention relates to novel method of synthesis of RNA utilizing N-2-acetyl protected guanine as nucleoside base, nucleosides, succinates, phosphoramidites, corresponding solid supports that are suitable for oligo deoxy nucleosides and RNA oligonucleotide synthesis. Our discovery using N-acetyl protected guanine as nucleoside base protecting group, which is significantly faster base labile protecting group, yet significantly more stable than commonly utilized-2-isobutyryl guanosine is a novel approach to obtain highest purity oligonucleotides. This approach is designed to lead to very high purity and very clean oligonucleotide, after efficient removal of the protecting groups, including acetyl group from guanine and to produce high purity therapeutic grade DNA oligonucleotides, RNA oligonucleotides, diagnostic DNA, diagnostic RNA for microarray platform. The deprotection of acetyl protecting groups of the natural deoxy and ribonucleosides occurs under substantially reduced time in contact with mild deprotection conditions such as mild bases, secondary amines for removal of such groups under such conditions would allows synthesis of various DNA and RNA of highest purity for diagnostics and therapeutic application. This approach is designed to lead to high purity large scale therapeutic grade oligonucleotide chimeras which consist of fluoro sugar modification in conjunction with deoxy nucleosides, ribonucleosides, modified base and modified sugar nucleosides. This approach is further designed to use acetyl guanine protecting group when other bases are sensitive nucleoside, and for use in oligo peptide synthesis and for support bound oligo nucleotides.

专利号:WO-2024185734-A1
优先权日:2023-03-03
标 题:Polyphosphorylated nucleoside, phosphate-activated nucleotide used for synthesis of polyphosphorylated nucleoside and method for synthesis of same, and method for synthesis of polyphosphorylated nucleoside using phosphate-activated nucleotide
发明人:KATAOKA MASANORI; FUKUI CHIHARU; TSUJI YOHEI; FUJIMURA Kazuma
权利人:NATIAS INC
摘要:The present invention provides: a polyphosphorylated nucleoside which has a structure represented by formula (I) and can be efficiently produced by a short process and a simple operation with use of a less expensive material; a phosphate-activated nucleotide which is used for the synthesis of the polyphosphorylated nucleoside and a method for the synthesis of this phosphate-activated nucleotide; and a method for the synthesis of a polyphosphorylated nucleoside using a phosphate-activated nucleotide. In the formula, B represents a protected or unprotected, natural or artificial nucleoside base; R 1 , R 2 , R 4 and R 5 each represent H or an alkyl group or the like, and R 1 , R 2 , R 4 and R 5 may be the same as or different from each other; X and Y each represents H, OH, OCH 3 or the like; h represents an integer of 1 to 3; p, n, m and q each represent 0 or an integer, and p, n, m and q are in no particular order; and (p + n + m + q) is an integer of 0 to 5,000.

专利号:US-8981076-B2
优先权日:2008-11-29
标 题 :Synthesis of N-FMOC protected deoxy nucleosides, ribo nucleosides, modified deoxy and ribo nucleosides, and phosphoramidites, and their use in oligonucleotide synthesis
发明人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P
权利人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P; CHEMGENES CORP
摘要:This invention relates to synthesis of novel -N-FMOC protected nucleosides, succinates, phosphoramidites, corresponding solid supports that are suitable for oligo deoxy nucleosides and RNA oligonucleotide synthesis. Our discovery using N-FMOC as nucleoside base protecting group, which is highly base labile protecting group is a novel approach to obtain highest purity oligonucleotides. This approach is designed to lead to very high purity and very clean oligonucleotide, after efficient removal of the protecting groups and to produce high purity therapeutic grade DNA oligonucleotides, RNA oligonucleotides, diagnostic DNA, diagnostic RNA for microarray platform. The deprotection of FMOC protecting groups of the natural deoxy and ribonucleosides occurs under very mild deprotection conditions such as mild bases, secondary and tertiary amines for removal of such groups under such conditions would allows synthesis of various DNA and RNA of highest purity for diagnostics and therapeutic application. This approach is further designed to use FMOC protecting group on various base sensitive nucleoside, and for use in oligo peptide synthesis and for support bound oligo nucleotides. DNA oligonucleotides containing 3′-end dA at the 3′-terminal will be produced using the FMOC-dA-supports would lead to much reduced M−1 deletion sequences, and thereby high purity.

专利号:US-12188072-B2
优先权日:2018-03-19
标题 :Compositions and methods for rapid in vitro synthesis of bioconjugate vaccines in vitro via production and N-glycosylation of protein carriers in detoxified prokaryotic cell lysates
发明人:JEWETT MICHAEL CHRISTOPHER; STARK JESSICA CAROL; DELISA MATTHEW P; JAROENTOMEECHAI THAPAKORN
权利人:UNIV NORTHWESTERN; UNIV CORNELL
摘要:Disclosed are methods, systems, components, and compositions for cell-free synthesis of glycosylated carrier proteins. The glycosylated carrier proteins may be utilized in vaccines, including anti-bacterial vaccines. The glycosylated carrier proteins may include a bacterial polysaccharide conjugated to a carrier, which may be utilized to generate an immune response in an immunized host against the polysaccharide conjugated to the carrier. The glycosylated carrier proteins may be synthesized in cell-free glycoprotein synthesis (CFGpS) systems using prokaryote cell lysates that are enriched in components for glycoprotein synthesis such as oligosaccharyltransferases (OSTs) and lipid-linked oligosaccharides (LLOs) including OSTs and LLOs associated with synthesis of bacterial O antigens.

专利号:US-8138330-B2
优先权日:2006-09-11
标 题 :Process for the synthesis of oligonucleotides
发明人:LEUCK MICHAEL; WOLTER ANDREAS; STUMPE ALFRED
权利人:LEUCK MICHAEL; WOLTER ANDREAS; STUMPE ALFRED; SIGMA ALDRICH CO LLC
摘要:The present invention discloses novel methods for the synthesis of oligonucleotides with nucleoside phosphoramidites on solid supports. The methods comprise the stepwise chain assembly of oligonucleotides on supports with 5′-acyl phosphoramidites. The synthesis cycles consist of a front end deprotection step which is conducted with a solution of a primary amine or a phenolate, a phosphoramidite coupling step with a 5′-acyl nucleoside phosphoramidite in the presence of an activator, a phosphite oxidation step and an optional capping step. The novel methods improve the quality of synthetic oligonucleotides due to the irreversibility of the front end deprotection step, which prevents the formation of deletion sequences, and due to the avoidance of acidic reagents in the synthesis cycles, which prevent the formation of depurination side products. The invention further discloses novel nucleoside phosphoramidite compositions wherein the phosphoramidites carry acyl front end protective groups which are cleavable with primary amines or phenolates. The invention is applicable to the synthesis of oligodeoxyribonucleotides, oligoribonucleotides and oligonucleotides with modifications in their sugar or phosphate groups.
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主要参考文献


1: Hardwick JS, Lane AN, Brown T. Epigenetic Modifications of Cytosine: Biophysical Properties, Regulation, and Function in Mammalian DNA. Bioessays. 2018 Mar;40(3). doi: 10.1002/bies.201700199. Epub 2018 Jan 25. Review. doi: 10.1002/tcr.201700088. Epub 2017 Dec 18. Review. pii: E2387. doi: 10.3390/ijms18112387. Review.
8: Block T, El-Osta A. Epigenetic programming, early life nutrition and the risk of metabolic disease. Atherosclerosis. 2017 Nov;266:31-40. doi: 10.1016/j.atherosclerosis.2017.09.003. Epub 2017 Sep 5. Review. Review. doi: 10.1016/j.gde.2017.07.011. Epub 2017 Sep 6. Review. doi: 10.1016/j.preteyeres.2017.08.003. Epub 2017 Aug 31. Review.
12: Miranda-Morales E, Meier K, Sandoval-Carrillo A, Salas-Pacheco J, Vázquez-Cárdenas P, Arias-Carrión O. Implications of DNA Methylation in Parkinson's Disease. Front Mol Neurosci. 2017 Jul 18;10:225. doi: 10.3389/fnmol.2017.00225. eCollection 2017. Review.

合成参考文献


参考文献:10.18632/aging.100106
摘要:Pegoraro G, Misteli T. The central role of chromatin maintenance in aging. Aging (Albany NY). 2009 Dec 09;1(12):1017–22.
参考文献:10.1021/tx9003962
摘要:Su DG, Taylor JS, Gross ML. A new photoproduct of 5-methylcytosine and adenine characterized by high-performance liquid chromatography and mass spectrometry. Chem Res Toxicol. 2010 Mar 15;23(3):474–9.
参考文献:10.1186/1471-2164-11-s1-s1
摘要:Tsai AG, Lieber MR. Mechanisms of chromosomal rearrangement in the human genome. BMC Genomics. 2010 Feb 10;11 Suppl 1():S1.
参考文献:10.1016/j.toxlet.2011.05.1039
摘要:Liu Q, Yang L, Gong C, Tao G, Huang H, Liu J, Zhang H, Wu D, Xia B, Hu G, Wang K, Zhuang Z. Effects of long-term low-dose formaldehyde exposure on global genomic hypomethylation in 16HBE cells. Toxicol Lett. 2011 Sep 10;205(3):235–40. doi: 10.1016/j.toxlet.2011.05.1039.
参考文献:10.1007/978-1-61779-188-8_3
摘要:Hari Y, Kodama T, Imanishi T, Obika S. 2'-O,4'-C-methyleneoxymethylene bridged nucleic acids (2',4'-BNA(COC)). Methods Mol Biol. 2011;764():31–57. doi: 10.1007/978-1-61779-188-8_3.
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