selenohomocystine | 960392-09-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: selenohomocystine
• 英文别名: (2S)-2-amino-4-[(3S)-3-amino-3-carboxypropyl]selanylbutanoic acid
• CAS: 960392-09-0
• 化学式: C₈H₁₆N₂O₄Se
• 分子量: 283.186
• InChiKey: HTVQZQMHALXTBF-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.87
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  selenohomocystine 、 5-碘-5-脱氧环磷腺苷 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以58%的产率得到Se-adenosylselenohomocysteine
  参考文献：
  名称：

  Large-Scale, Protection-Free Synthesis of Se-Adenosyl-l-selenomethionine Analogues and Their Application as Cofactor Surrogates of Methyltransferases

  摘要：

  S-Adenosyl-L-methionine (SAM) analogues have previously demonstrated their utility as chemical reporters of methyltransferases. Here we describe the facile, large-scale synthesis of Se-alkyl Se-adenosyl-L-selenomethionine (SeAM) analogues and their precursor, Se-adenosyl-L-selenohomocysteine (SeAH). Comparison of SeAM analogues with their equivalent SAM analogues suggests that sulfonium-to- selenonium substitution can enhance their compatibility with certain protein methyltransferases, favoring otherwise less reactive SAM analogues. Ready access to SeAH therefore enables further application of SeAM analogues as chemical reporters of diverse methyltransferases.

  DOI：

  10.1021/ol501169y
• 作为产物：
  描述：

  L(+)-2-氨基-4-溴丁酸氢溴酸盐 在 selenium 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以84%的产率得到selenohomocystine
  参考文献：
  名称：

  Large-Scale, Protection-Free Synthesis of Se-Adenosyl-l-selenomethionine Analogues and Their Application as Cofactor Surrogates of Methyltransferases

  摘要：

  S-Adenosyl-L-methionine (SAM) analogues have previously demonstrated their utility as chemical reporters of methyltransferases. Here we describe the facile, large-scale synthesis of Se-alkyl Se-adenosyl-L-selenomethionine (SeAM) analogues and their precursor, Se-adenosyl-L-selenohomocysteine (SeAH). Comparison of SeAM analogues with their equivalent SAM analogues suggests that sulfonium-to- selenonium substitution can enhance their compatibility with certain protein methyltransferases, favoring otherwise less reactive SAM analogues. Ready access to SeAH therefore enables further application of SeAM analogues as chemical reporters of diverse methyltransferases.

  DOI：

  10.1021/ol501169y

文献信息

• Large-Scale, Protection-Free Synthesis of <i>Se</i>-Adenosyl-<scp>l</scp>-selenomethionine Analogues and Their Application as Cofactor Surrogates of Methyltransferases
  作者：Ian R. Bothwell、Minkui Luo

  DOI：10.1021/ol501169y

  日期：2014.6.6

  S-Adenosyl-L-methionine (SAM) analogues have previously demonstrated their utility as chemical reporters of methyltransferases. Here we describe the facile, large-scale synthesis of Se-alkyl Se-adenosyl-L-selenomethionine (SeAM) analogues and their precursor, Se-adenosyl-L-selenohomocysteine (SeAH). Comparison of SeAM analogues with their equivalent SAM analogues suggests that sulfonium-to- selenonium substitution can enhance their compatibility with certain protein methyltransferases, favoring otherwise less reactive SAM analogues. Ready access to SeAH therefore enables further application of SeAM analogues as chemical reporters of diverse methyltransferases.