5-formyl-2',3'-O-isopropylideneuridine | 60170-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-formyl-2',3'-O-isopropylideneuridine
• 英文别名: 1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2,4-dioxopyrimidine-5-carbaldehyde
• CAS: 60170-16-3
• 化学式: C₁₃H₁₆N₂O₇
• 分子量: 312.279
• InChiKey: YAPTZLUELYTUCL-TURQNECASA-N

物化性质

• 密度：
  1.479±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-formyl-2',3'-O-isopropylideneuridine 在 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 25.0~200.0 ℃ 、666.61 Pa 条件下， 反应 36.83h， 生成 2’,3’邻异亚丙基尿苷
  参考文献：
  名称：

  Insight into the Chemical Mechanism of Thymidylate Synthase-Catalyzed Reaction Through the Evaluation of Chemical Models: The Role of C6 Sulfhydryl Addition During the Reductive Elimination Step of the Reaction1

  摘要：

  Thymidylate synthase catalyzes the last step of the de novo synthesis of thymidine-5'-monophosphate (TMP), which has long been a target for the development of effective anticancer agents. Model compounds (15, 16, 17) were used to study the effect of C6 nucleophilic addition on the reductive elimination step of the TS-catalyzed reaction. Results suggest that C6 addition facilitates the reductive elimination of the H(2)folate moiety of the ternary intermediate (3). Therefore, the reaction pathway (pathway (b)) with the participation of C6 sulfhydryl addition during the reductive elimination process is the energetically favored process. Consequently, the elimination of the cysteine sulfhydryl group from the C6 position is the last step of the reaction before the dissociation of the products from the enzyme. (C) 1994 Academic Press, Inc.

  DOI：

  10.1006/bioo.1994.1034
• 作为产物：
  描述：

  2’,3’邻异亚丙基尿苷 在 manganese(IV) oxide 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 28.0h， 生成 5-formyl-2',3'-O-isopropylideneuridine
  参考文献：
  名称：

  Photo‐Facilitated Detection and Sequencing of 5‐Formylcytidine RNA

  摘要：

  Abstract5‐Formylcytidine (f5C) is one of the epigenetic nucleotides in tRNA. Despite the evident importance of f5C in gene expression regulation, little is known about its exact amount and position. To capture this information, we developed a modification‐specific functionalization with a semi‐stabilized ylide. The chemical labelling exhibited a high selectivity towards f5C and allowed distinction from similar 5‐formyluridine. We realized a detection strategy based on the fluorescence signal of the cyclization product 4,5‐pyridin‐2‐amine‐cytidine paC, which exhibited a high quantum yield. The results clearly identified f5C with a limit of detection at 0.58 nM. This method altered the hydrogen bonding activities of f5C and modulated its reverse transcription signature in its sequencing profile. We showed that f5C can be detected from tRNA segments with a single‐base resolution. Taken together, this approach is a sensitive, antibody‐free, and applicable detection and sequencing method for f5C‐containing RNA.

  DOI：

  10.1002/anie.202210652

文献信息

• mt-tRNA Components: Synthesis of (2-Thio)Uridines Modified with Blocked Glycine/Taurine Moieties at C-5,1
  作者：Grazyna Leszczynska、Piotr Leonczak、Agnieszka Dziergowska、Andrzej Malkiewicz

  DOI：10.1080/15257770.2013.838261

  日期：2013.11.2

  5-carboxymethylaminomethyl(-2-thio)uridine (cmnm5(s2)U) and 5-taurinomethyl(-2-thio)uridine (τm5(s2)U) with a blocked amino acid function. 2-(Trimethylsilyl)ethyl and 2-(p-nitrophenyl)ethyl esters of glycine and 2-(2,4,5-trifluorophenyl)ethyl ester of taurine were selected as protection of carboxylic and sulfonic acid residues, respectively. The first synthesis of 5-formyl-2′,3′-O-isopropylidene-2-thiouridine

  在本文中，我们讨论了在三乙酰氧基硼氢化钠（NaBH（OAc）3）存在下，用甘氨酸或牛磺酸酯对5-甲酰基-2'，3'-O-异亚丙基（-2-硫基）尿苷进行氨基化还原胺化的有用性。用于合成天然线粒体（mt）tRNA组分5-羧甲基氨基甲基（-2-硫代）尿苷（cmnm5（s2）U）和5-牛磺基甲基（-2-硫代）尿苷（τm5（s2）U）氨基酸功能。分别选择甘氨酸的2-（三甲基甲硅烷基）乙酯和2-（对硝基苯基）乙酯和牛磺酸的2-（2,4,5-三氟苯基）乙酯作为羧酸和磺酸残基的保护剂。还报道了5-甲酰基-2'，3'-O-异亚丙基-2-硫尿苷的首次合成。
• Novel entry to the synthesis of (<i>S</i>)- and (<i>R</i>)-5-methoxycarbonylhydroxymethyluridines – a diastereomeric pair of wobble tRNA nucleosides
  作者：Robert Borowski、Agnieszka Dziergowska、Elzbieta Sochacka、Grazyna Leszczynska

  DOI：10.1039/c9ra08548c

  日期：——

  equimolar mixtures of (S)- and (R)-diastereomers of 5-methoxycarbonylhydroxymethyluridine (mchm5U) have been developed. The first method involved α-hydroxylation of a 5-malonate ester derivative of uridine (5) with SeO2, followed by transformation to (S)- and (R)-5-carboxymethyluridines (cm5U, 8) and, finally, into the corresponding methyl esters. In the second approach, (S)- and (R)-mchm5-uridines were

  已经开发了两种制备5-甲氧基羰基羟甲基尿苷 (mchm 5 U)的 ( S )- 和 ( R )- 非对映异构体的几乎等摩尔混合物的新方法。第一种方法涉及用 SeO 2对尿苷 ( 5 )的 5-丙二酸酯衍生物进行 α-羟基化，然后转化为 ( S )- 和 ( R )-5-羧甲基尿苷 (cm 5 U, 8 )，最后，转化为相应的甲酯。在第二种方法中，( S )-和( R )-mchm 5-尿苷是从5-甲酰尿苷衍生物( 9)通过水解在含5-氰醇的尿苷( 10b )与甲醇的酸催化反应中制备的亚胺酸盐( 11 )。在这两种方法中，mchm 5 U 的 ( S )- 和 ( R ) 非对映异构体均通过制备型 C18 RP HPLC 有效分离。
• Site-selected incorporation of 5-carboxymethylaminomethyl(-2-thio)uridine into RNA sequences by phosphoramidite chemistry
  作者：Grazyna Leszczynska、Jakub Pięta、Karolina Wozniak、Andrzej Malkiewicz

  DOI：10.1039/c3ob42302f

  日期：——

  report the first site-selected incorporation of cmnm5U and cmnm5s2U into RNA sequences by phosphoramidite chemistry on a CPG solid support. Trifluoroacetyl and 2-(trimethylsilyl)ethyl were selected for the protection of the amine and carboxyl functions, respectively.

  5-羧甲基氨基甲基尿苷（cmnm 5 U）和5-羧甲基氨基甲基-2-硫尿苷（cmnm 5 s 2 U）位于几个胞质和线粒体tRNA序列的摆动位置。在本文中，我们报告了通过CPG固体支持物上的亚磷酰胺化学方法将cmnm 5 U和cmnm 5 s 2 U首次定点掺入RNA序列。选择三氟乙酰基和2-（三甲基甲硅烷基）乙基分别用于保护胺和羧基官能团。
• A chemical model for the fragmentation reaction in thymidylate synthase catalysis. Synthesis and evaluation of a 5-methylene-1-(1,2,3,4-tetrahydroquinolyl)-6-allyluridine
  作者：John R. Kagel、Binghe Wang、Mathias P. Mertes

  DOI：10.1021/jo00062a014

  日期：1993.5

  Compounds 5 and 6 were synthesized as models to investigate the reactivity of proposed intermediate 2 in thymidylate synthase (TS) catalysis as it fragments to form dTMP. The mechanism of the fragmentation (homolytic or heterolytic) of model 6 was determined via subsequent interaction of the fragmented center with the C6 allyl substituent. The results were consistent with an ionic fragmentation of 6, followed by loss of an allylic proton, and subsequent thermal electrocyclic or Diels-Alder reactions of the resulting trienes 13 and 14, respectively. Independent generation of radicals analogous to that produced from a radical fragmentation of model 6 did not result in formation of trienes 13 and 14.
• Ahmed, A. F. Sayed, Journal of Chemical Research, Miniprint, 1998, # 11, p. 3011 - 3018
  作者：Ahmed, A. F. Sayed

  DOI：——

  日期：——