胸腺嘧啶脱氧核苷3-单磷酸铵盐水合物 | 2642-43-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核糖核苷3'-磷酸盐
• 中文名称: 胸腺嘧啶脱氧核苷3-单磷酸铵盐水合物
• 中文别名: 胸酰嘧啶-3-磷酸
• 英文名称: thymidine 3'-monophosphate
• 英文别名: 3'-thymidine monophosphate；[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] dihydrogen phosphate
• CAS: 2642-43-5
• 化学式: C₁₀H₁₅N₂O₈P
• 分子量: 322.211
• InChiKey: XXYIANZGUOSQHY-XLPZGREQSA-N

物化性质

• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  8

SDS

Version 1.4
Regulation (EC) No 1907/2006

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1 - Product and Company Information

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Product Name THYMIDINE 3'-MONOPHOSPHATE AMMONIUM
SALT HYDRATE

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2 - Hazards Identification

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3 - Composition/Information on Ingredients

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Product Name CAS # EC no Annex I
Index Number
THYMIDINE 3'-MONOPHOSPHATE None None None
AMMONIUM SALT HYDRATE
Formula C10H14N2O8P · xNH3 · yH2O
Molecular Weight 321,2000 AMU

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4 - First Aid Measures

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5 - Fire Fighting Measures

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6 - Accidental Release Measures

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7 - Handling and Storage

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STORAGE
Store at -20°C

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8 - Exposure Controls / Personal Protection

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9 - Physical and Chemical Properties

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pH N/A
BP/BP Range N/A
MP/MP Range N/A
SIGMA www.molbase.com
Flash Point N/A
Flammability N/A
Autoignition Temp N/A
Oxidizing Properties N/A
Explosive Properties N/A
Explosion Limits N/A
Vapor Pressure N/A
Partition Coefficient N/A
Viscosity N/A
Vapor Density N/A
Saturated Vapor Conc. N/A
Evaporation Rate N/A
Bulk Density N/A
Decomposition Temp. N/A
Solvent Content N/A
Water Content N/A
Surface Tension N/A
Conductivity N/A
Miscellaneous Data N/A
Solubility N/A

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10 - Stability and Reactivity

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11 - Toxicological Information

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12 - Ecological Information

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No data available.

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13 - Disposal Considerations

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14 - Transport Information

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RID/ADR
Non-hazardous for road transport.
IMDG
Non-hazardous for sea transport.
IATA
Non-hazardous for air transport.

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15 - Regulatory Information

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Caution: Substance not yet fully tested (EU).
COUNTRY SPECIFIC INFORMATION
Germany
WGK: 3
Self-Classification

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16 - Other Information

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WARRANTY
The above information is believed to be correct but does not
purport to be all inclusive and shall be used only as a guide. The
SIGMA www.molbase.com
information in this document is based on the present state of our
knowledge and is applicable to the product with regard to
appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Inc.,
shall not be held liable for any damage resulting from handling or
from contact with the above product. See reverse side of invoice
or packing slip for additional terms and conditions of sale.
Copyright 2010 Co. License granted to make
unlimitedpaper copies for internal use only.
DISCLAIMER
For R&D use only. Not for drug, household or other uses.
SIGMA www.molbase.com

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  胸腺嘧啶脱氧核苷3-单磷酸铵盐水合物 在 cerium(III) chloride 、 HEPES buffer 、 氧气 作用下， 以 水 为溶剂， 生成 beta-胸苷
  参考文献：
  名称：

  Hydrolysis of phosphomonoesters in nucleotides by cerium(IV) ions. Highly selective hydrolysis of monoester over diester in concentrated buffers

  摘要：

  在生理条件下，核苷酸中的磷酸单酯可被 CeIV 离子有效水解。在 pH 值为 7.2、温度为 50 °C 的条件下（[CeIV] = 10 mM），残基的半衰期约为 10 分钟。CeIV 离子水解磷酸单酯的速度快于水解磷酸二酯的速度。值得注意的是，使用浓缩缓冲溶液（TRIS 和 HEPES）可显著提高单酯水解对二酯水解的选择性。在 500 mM TRIS 缓冲溶液中，pdA 和 dAp 的水解速度分别是 d(ApA) 的 500 倍和 580 倍，而在 50 mM TRIS 缓冲溶液中的相应比率分别为 85 倍和 90 倍。在这些浓缩缓冲液中，CeIV 可以选择性地去除 d(pApA)的末端单磷酸。

  DOI：

  10.1039/a701481c
• 作为产物：
  描述：

  保护胸苷 在 sodium hydroxide 、 TPS-TAZ 、 溶剂黄146 作用下， 以 吡啶 、 乙醇 、 水 为溶剂， 反应 2.83h， 生成 胸腺嘧啶脱氧核苷3-单磷酸铵盐水合物
  参考文献：
  名称：

  核苷磷酸化的新方法

  摘要：

  开发了一种新的磷酸化试剂2- O-（4,4'-二甲氧基三苯甲基）乙基磺酰lethan-2'-基磷酸酯（1），用于磷酸化核苷的伯醇和仲醇。在许多研究的实例中，磷酸化步骤的收率非常好（约80％至95％）。该方法不仅在核苷和核苷酸化学中，而且在诸如碳水化合物和氨基酸的生物分子的磷酸化中都有广泛的应用潜力。

  DOI：

  10.1016/s0040-4039(00)01251-x

文献信息

• The synthesis of di- and oligo-nucleotides containing a phosphorodithioate internucleotide linkage with one of the sulfur atoms in a 5′-bridging position
  作者：Magdalena Olesiak、Wojciech J. Stec、Andrzej Okruszek

  DOI：10.1039/b901791g

  日期：——

  phosphorodithioate linkage is described, wherein one of the sulfur atoms occupies a 5′-bridging position. Representative dinucleotides possessing such a bond were synthesized by S-alkylation of nucleoside-3′-O-phosphorodithioates with 5′-halogeno-5′-deoxy-nucleosides. A fully protected dithymidylate containing internucleotide 5′-S-phosphorodithioate linkage was converted into a 3′-O-phosphoramidite

  描述了一种新型的核苷酸间二硫代磷酸酯键，其中一个硫原子占据5'-桥接位置。具有这种键的代表性二核苷酸是通过将核苷-3'- O-二硫代磷酸酯与5'-卤素-5'-脱氧核苷进行S-烷基化而合成的。将含有核苷酸间5'- S-二硫代磷酸酯键的完全保护的二胸苷酸转化为3'- O-亚磷酰胺衍生物，并用于将修饰的二核苷酸引入寡核苷酸序列的预定位置。5'- S发现二核苷酸类似物中的β-二硫代磷酸酯键抗蛇毒PDE和核酸酶P1的核酸降解。然而，在小牛脾PDE处理下，观察到5'- S-二硫代磷酸二硫代二胸苷类似物的非对映异构体的P-立体选择性降解。在碘的存在下碘溶液容易降解新的5'- S-磷酸二硫酯键。水。还发现含有单个5'- S-磷酸二硫酯键的寡胸苷酸酯与其互补序列形成弱得多的双链体。
• SYNTHESIS OF NUCLEOSIDE PHOSPHOTRIESTERS CONTAINING AMIDATE OR THIOATE FUNCTIONS
  作者：Stan A. A. van Boeckel、Gijs van der Marel、Gerry Wille、Jacq H. van Boom

  DOI：10.1246/cl.1981.1725

  日期：1981.12.5

  Phosphorylation of properly protected nucleosides with aryl or alkyl phosphorodichloridates, in the presence of 1-hydroxybenzotriazole, gives phosphorylated intermediates which react smoothly with different amine or thiol functions to afford the corresponding amidate or thioate phosphotriester derivatives.

  在 1-羟基苯并三唑的存在下，用芳基或烷基二氯磷酸酯对适当保护的核苷进行磷酸化，得到磷酸化的中间体，该中间体与不同的胺或硫醇官能团顺利反应，得到相应的酰胺或硫代磷酸三酯衍生物。
• Oligonucleotides and nucleotidopeptides. XLII. Efficacy of the intramolecular influence of the carboxy groups of amino acids in nucleotidyl-(P → N)-amino acids (peptides) as a function of their positions
  作者：B. A. Yuodka、L. E. Lioranchaite、V. R. Baltenas

  DOI：10.1007/bf00579428

  日期：1982.11

  has been established that remote carboxy groups in nucleotidyl-(5′ → N)-β-alanine and -alanylalanine do not affect the mechanism of the cleavage of the phosphoramide center. The situation is different in the case of nucleotidyl-(5′ → Nɛ)-lysine. It has been shown that in the 3′-phenylalanine derivative of dTMP, the influence of the α-carboxy group of the amino acid is only half as great as in the 5′-analog

  已经确定核苷酸基-(5' → N)-β-丙氨酸和-丙氨酸丙氨酸中的远程羧基不影响磷酰胺中心裂解的机制。核苷酸-(5′ → Nɛ)-赖氨酸的情况有所不同。已经表明，在 dTMP 的 3'-苯丙氨酸衍生物中，氨基酸的 α-羧基的影响仅为 5'-类似物的一半。寡核苷酸基-(Pin → N)-氨基酸中氨基酸的α-羧基也削弱了磷酰胺中心裂解的机制。
• A general approach to nucleoside 3′- and 5′- monophosphates
  作者：Y. Hayakawa、S. Wakabayashi、T. Nobori、R. Noyori

  DOI：10.1016/s0040-4039(00)96095-7

  日期：1987.1

  Diallyloxyphosphorylation of nucleoside hydroxyls followed by palladium(0)-catalyzed deallylation provides a new, general method for the preparation of the 3′- and 5′-monophosphates.

  核苷羟基的二烯丙氧基磷酸化反应，再由钯（0）催化的脱醛反应，为制备3'-和5'-单磷酸酯提供了一种新的通用方法。
• Precolumn Derivatization of Nucleotides Based on Fluorescent Carbamate Formation on the Sugar Moieties in High-Performance Liquid Chromatography.
  作者：Hiroaki NAGAOKA、Hitoshi NOHTA、Mikihiko SAITO、Yosuke OHKURA

  DOI：10.1248/cpb.40.2559

  日期：——

  The fluorescence derivatization of nucleotides with 2-(5-chlorocarbonyl-2-oxazolyl)5, 6-methylenedioxybenzo-furan in the presence of sodium azide and the separation of the derivatives by high-performance liquid chromatography are described. The reagent reacts with 5'-terminal hydroxyl groups of nucleotides to produce the correspoding fluorescent carbamates. The derivatives of mono- and oligonucleotides are separated by chromatography on a reversed phase column (TSKgel ODS-80TM) and the derivatices of octa- and deca-nucletides on a size exclusion column (TSKgel G3000SWXL). The detection limits (signal-to-noise ratio-3) are 0.8-6.0 pmol on column. 5'-Phosphorylated nucleotide also gives a fluorescent derivative after alkaline phosphatase-mediated dephosphorylation.

  描述了核苷酸与2-(5-氯碳酰基-2-噁唑基)5,6-亚甲基二氧苯并呋喃在存在叠氮化钠的条件下进行荧光衍生化，并通过高效液相色谱分离衍生物。该试剂与核苷酸的5'末端羟基反应，生成相应的荧光氨基甲酸酯。单核苷酸和寡核苷酸的衍生物通过反相色谱柱（TSKgel ODS-80TM）分离，而八核苷酸和十核苷酸的衍生物则在尺寸排阻柱（TSKgel G3000SWXL）上分离。检测限（信噪比3）为0.8-6.0 pmol。在碱性磷酸酶介导的脱磷酸化后，5'-磷酸化核苷酸也会生成荧光衍生物。