1''-[3-(2'-deoxy-α-D-erythropentafuranosyl)-3H-imidazo[2,1-i]purin-7-yl]heptane-2''-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 1''-[3-(2'-deoxy-α-D-erythropentafuranosyl)-3H-imidazo[2,1-i]purin-7-yl]heptane-2''-one
• 英文别名: 1''-[3-(2'-deoxy-β-D-erythro-pentafuranosyl)-3H-imidazo[2,1-i]purin-7-yl]heptan-2''-one；1''-[3-(2'-deoxy-β-D-erythropentafuranosyl)-3H-imidazo[2,1-i]purin-7-yl]heptane-2''-one；dA-ONE；1-[3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazo[2,1-f]purin-7-yl]heptan-2-one
• 化学式: C₁₉H₂₅N₅O₄
• 分子量: 387.439
• InChiKey: RVCFSFNCHSAGKY-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2'-脱氧腺苷 以 乙醇 、 水 为溶剂， 反应 96.0h， 生成 1''-[3-(2'-deoxy-α-D-erythropentafuranosyl)-3H-imidazo[2,1-i]purin-7-yl]heptane-2''-one
  参考文献：
  名称：

  衍生自4-氧代-2-壬烯醛（脂质过氧化的新产物）的2'-脱氧腺苷加合物的表征。

  摘要：

  通过液相色谱/质谱法分析2'-脱氧腺苷与4-氧代-2-壬烯醛之间的反应，发现存在三种主要产物（加合物A（1），A（2）和B）。加合物A（1）和A（2）是异构体；它们在室温下相互转化，并且每个都容易脱水形成加合物B。通过碰撞诱导解离与多串联质谱联用获得的加合物B的质谱特征与取代的乙炔加合物所预期的一致。NMR光谱显示加合物B的结构与取代的乙炔-2'-脱氧腺苷加合物1''-[3-（2'-脱氧-β-D-赤藓型呋喃呋喃糖基）-3H-咪唑并[2，1 -i]嘌呤-7-基]庚烷-2'-一。结构的明确证据来自加合物A（1）和A（2）（加合物B的前体）与硼氢化钠的反应。加合物A（1）和A（2）各自形成相同的还原产物，其中包含八个额外的氢原子。该还原产物的质谱特性确定了2'-脱氧腺苷的环外氨基（N（6））连接到4-氧代-2-壬烯醛的C-1。还显示了4-氧代-2-壬烯醛与小牛胸腺DNA的反应导致形成取代的乙醇加

  DOI：

  10.1021/tx000057z

文献信息

• Formation of a Substituted 1,<i>N</i>⁶-Etheno-2‘-deoxyadenosine Adduct by Lipid Hydroperoxide-Mediated Generation of 4-Oxo-2-nonenal
  作者：Diane Rindgen、Seon Hwa Lee、Masaharu Nakajima、Ian A. Blair

  DOI：10.1021/tx0000771

  日期：2000.9.1

  13-hydroperoxylinoleic acid by liquid chromatography/constant neutral loss mass spectrometry revealed the presence of two major products (adducts A and B). Adduct A was shown to be a mixture of two isomers (A(1) and A(2)) that each decomposed with the loss of water to form adduct B. The mass spectral characteristics of adduct B were consistent with the substituted 1, N(6)-etheno-2'-deoxyadensoine adduct 1' '-[3-

  通过液相色谱/恒定中性损失质谱法分析2'-脱氧腺苷和13-氢过氧亚油酸之间的反应，发现存在两种主要产物（加合物A和B）。加合物A被证明是两种异构体的混合物（A（1）和A（2）），每一种异构体都随着水的流失而分解形成加合物B。加合物B的质谱特性与被取代的1，N （6）-乙炔基-2'-脱氧腺苷加合物1''-[3-（2'-脱氧β-D-赤型-五呋喃糖基）-3H-咪唑并[2,1-i]嘌呤-7-基]庚-2'--一。当用合成的4-氧代-2-壬烯醛处理2'-脱氧腺苷时，形成加合物A（1），A（2）和B，这表明它是由13-氢过氧亚油酸的分解形成的。加合物A（1），A（2），当在Fe（II）存在下孵育13-氢过氧亚油酸和2'-脱氧腺苷时，观察到B。因此，4-氧代-2-壬烯醛最有可能通过均溶过程形成。尽管在4-羟基-2-壬烯醛和2'-脱氧腺苷之间的反应中形成了加合物A（1），A（2）和B，但观察到许多其他产物。
• MR1 LIGANDS AND PHARMACEUTICAL COMPOSITIONS FOR IMMUNOMODULATION
  申请人：Universität Basel

  公开号：EP3889602A1

  公开（公告）日：2021-10-06

  The invention relates to a method for modulating an interaction between an MR1 polypeptide and an MR1-specific T cell receptor molecule, whereby a MR1 polypeptide is contacted with a MR1 ligand compound that is a nucleobase adduct product reflecting a state of metabolic distress of a eukaryotic cell. The invention further relates to the use of compounds identified as MR1 ligands in vaccination or modulation of an MR1-restricted immune response.

  本发明涉及一种调节MR1多肽与MR1特异性T细胞受体分子之间相互作用的方法，其中MR1多肽与MR1配体化合物接触，MR1配体化合物是反映真核细胞代谢窘迫状态的核碱基加合物产物。 本发明进一步涉及鉴定为 MR1 配体的化合物在疫苗接种或调节 MR1 限制性免疫反应中的用途。
• Identification of Octenal-Related dA and dC Adducts Formed by Reactions with a Hemin-ω-6-fat Peroxidation Model System
  作者：Kazuaki Kawai、Yuya Kawasaki、Yumiko Kubota、Tomoyuki Kimura、Ryuichi Sawa、Tomonari Matsuda、Hiroshi Kasai

  DOI：10.1021/tx400245a

  日期：2013.10.21

  Deoxynucleosides were reacted in a lipid peroxidation model system, emulsified hemin-ethyl linoleate, and the adducts thus produced were analyzed by HPLC. Substantial amounts of stable adducts were detected in the dA- and dC-reaction mixtures. The structures of the major dA and dC adducts, other than the known 4-oxo-2-nonenal adducts, were determined to be etheno-type adducts, with a C-6 side chain bearing an a-hydroxyl-group. These results suggested that the substance involved in adduct formation is 2,3-epoxyoctanal. This compound showed mutagenicity in Salmonella strains TA 100 and TA 104 without the S-9 mix. In addition, based on the structure of a minor dC adduct, another possibly involved mutagen, 4-oxo-2-octenal, was proposed. These mutagens may be formed during storage and cooking of food, or during digestion, and may be involved in human cancers.
• [EN] MR1 LIGANDS AND PHARMACEUTICAL COMPOSITIONS FOR IMMUNOMODULATION<br/>[FR] LIGANDS MR1 ET COMPOSITIONS PHARMACEUTIQUES POUR IMMUNOMODULATION
  申请人：UNIV BASEL

  公开号：WO2021144475A1

  公开（公告）日：2021-07-22

  The invention relates to a method for modulating an interaction between an MR1 polypeptide and an MR1-specific T cell receptor molecule, whereby a MR1 polypeptide is contacted with a MR1 ligand compound that is a nucleobase adduct product reflecting a state of metabolic distress of a cell. The invention further relates to the use of compounds identified as MR1 ligands in vaccination or modulation of an MR1-restricted immune response.
• Characterization of 2‘-Deoxyadenosine Adducts Derived from 4-Oxo-2-nonenal, a Novel Product of Lipid Peroxidation
  作者：Seon Hwa Lee、Diane Rindgen、Roy H. Bible,、Elisabeth Hajdu、Ian A. Blair

  DOI：10.1021/tx000057z

  日期：2000.7.1

  exocyclic amino group (N(6)) of 2'-deoxyadenosine was attached to C-1 of the 4-oxo-2-nonenal. The reaction of 4-oxo-2-nonenal with calf thymus DNA was also shown to result in the formation of substituted ethano adducts A(1) and A(2) and substituted etheno adduct B. Adduct B was formed in amounts almost 2 orders of magnitude greater than those of adducts A(1) and A(2). This was in keeping with the observed

  通过液相色谱/质谱法分析2'-脱氧腺苷与4-氧代-2-壬烯醛之间的反应，发现存在三种主要产物（加合物A（1），A（2）和B）。加合物A（1）和A（2）是异构体；它们在室温下相互转化，并且每个都容易脱水形成加合物B。通过碰撞诱导解离与多串联质谱联用获得的加合物B的质谱特征与取代的乙炔加合物所预期的一致。NMR光谱显示加合物B的结构与取代的乙炔-2'-脱氧腺苷加合物1''-[3-（2'-脱氧-β-D-赤藓型呋喃呋喃糖基）-3H-咪唑并[2，1 -i]嘌呤-7-基]庚烷-2'-一。结构的明确证据来自加合物A（1）和A（2）（加合物B的前体）与硼氢化钠的反应。加合物A（1）和A（2）各自形成相同的还原产物，其中包含八个额外的氢原子。该还原产物的质谱特性确定了2'-脱氧腺苷的环外氨基（N（6））连接到4-氧代-2-壬烯醛的C-1。还显示了4-氧代-2-壬烯醛与小牛胸腺DNA的反应导致形成取代的乙醇加