(S_SR_C)-N-t-Boc-L-methionine sulfoxide | 3913-77-7

• 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: (S_SR_C)-N-t-Boc-L-methionine sulfoxide
• 英文别名: (S)-N-BOC-L-methionine sulphoxide；tert-Butyloxycarbonylmethionin-d-sulfoxid；(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-[(S)-methylsulfinyl]butanoic acid
• CAS: 3913-77-7
• 化学式: C₁₀H₁₉NO₅S
• 分子量: 265.331
• InChiKey: FVSDTYGQCVACMH-SKLCBMLGSA-N

物化性质

• 沸点：
  509.3±45.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  对硝基苯酚 、 (S_SR_C)-N-t-Boc-L-methionine sulfoxide 在 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-Butyloxycarbonylmethionin-<4-nitrophenylester>-d-sulfoxid
  参考文献：
  名称：

  多肽的研究。XXXI。与牛胰腺核糖核酸酶N位点有关的合成肽（位置12-20）。

  摘要：

  DOI：

  10.1021/ja01081a041
• 作为产物：
  描述：

  Boc-L-蛋氨酸 在 Beauveria Bassiana ATCC 7159 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成 (S_SR_C)-N-t-Boc-L-methionine sulfoxide 、 (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-[(R)-methylsulfinyl]butanoic acid
  参考文献：
  名称：

  Biocatalytic and chemical routes to all the stereoisomers of methionine and ethionine sulfoxides

  摘要：

  Biotransformations of the N-phthaloyl derivatives of D- and L-methionine and of D- and L-ethionine by Beauveria bassiana ATCC 7159 or Beauveria caledonica ATCC 64970 produce the corresponding (S-S) sulfoxides in good yield and diastereomeric excess. Pure (SSSC) diastereomers can be obtained from L-series substrates by crystallisation of the biotransformation extract, and the corresponding (SSRC) products obtained from D-series substrates by chromatography of the biotransformation extract. Hydrogen peroxide-catalysed oxidation of the N-phthaloyl derivatives of D- and L-methionine and of D- and L-ethionine gives diastereomeric mixtures from which the (SSSC) and (RSRC) diastereomers can be obtained by crystallisation, and the (SSRC) and (RSSC) diastereomers obtained by chromatography. N-Cbz- and N-t-Boc methionines are also converted to sulfoxides with predominant (S-S) configuration by both B, bassiana and B. caledonica, but the isolated yields and d.e. of products were generally lower than those obtained from the N-phthaloyl substrates.Removal of the N-phthaloyl group from diastereomerically pure methionine and ethionine sulfoxides gave the corresponding amino acid sulfoxides in high yield; removal of N-Cbz and N-t-Boc groups from protected methionine sulfoxides was also achieved without loss of configuration at sulfur. (C) 1994 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00271-2

文献信息

• Optisch aktive Aminosäuresulfoxid- und -sulfon-Derivate, ihre Herstellung, ihre Polymerisation und Verwendung als Adsorbentien für die chromatographische Racematspaltung
  申请人：BAYER AG

  公开号：EP0576949A1

  公开（公告）日：1994-01-05

  Die Erfindung betrifft neue optisch aktive Aminosäurederivate der allgemeinen Formel (I) in welcher n, R, R₁, R₂, R₃, X und A die in der Beschreibung angegebene Bedeutung haben, die Sulfoxid- bzw. Sulfongruppen enthalten, zwei grundsätzliche Verfahrenswege zu deren Herstellung aus schwefelhaltigen Aminosäuren, die Polymerisation dieser Monomeren und die Verwendung der Polymeren als optisch aktive Adsorbentien für die chromatographische Trennung von Racematen in die Enantiomere.

  本发明涉及通式 (I) 的新光学活性氨基酸衍生物 其中 n、R、R₁、R₂、R₃、X 和 A 具有说明中给出的含义，它们含有亚砜基团或砜基团；从含硫氨基酸制备它们的两种基本工艺路线；这些单体的聚合；以及将聚合物用作光学活性吸附剂，用于色谱分离外消旋体和对映体。
• Biocatalytic and chemical routes to all the stereoisomers of methionine and ethionine sulfoxides
  作者：Herbert L Holland、Peter R Andreana、Frances M Brown

  DOI：10.1016/s0957-4166(99)00271-2

  日期：1999.7

  Biotransformations of the N-phthaloyl derivatives of D- and L-methionine and of D- and L-ethionine by Beauveria bassiana ATCC 7159 or Beauveria caledonica ATCC 64970 produce the corresponding (S-S) sulfoxides in good yield and diastereomeric excess. Pure (SSSC) diastereomers can be obtained from L-series substrates by crystallisation of the biotransformation extract, and the corresponding (SSRC) products obtained from D-series substrates by chromatography of the biotransformation extract. Hydrogen peroxide-catalysed oxidation of the N-phthaloyl derivatives of D- and L-methionine and of D- and L-ethionine gives diastereomeric mixtures from which the (SSSC) and (RSRC) diastereomers can be obtained by crystallisation, and the (SSRC) and (RSSC) diastereomers obtained by chromatography. N-Cbz- and N-t-Boc methionines are also converted to sulfoxides with predominant (S-S) configuration by both B, bassiana and B. caledonica, but the isolated yields and d.e. of products were generally lower than those obtained from the N-phthaloyl substrates.Removal of the N-phthaloyl group from diastereomerically pure methionine and ethionine sulfoxides gave the corresponding amino acid sulfoxides in high yield; removal of N-Cbz and N-t-Boc groups from protected methionine sulfoxides was also achieved without loss of configuration at sulfur. (C) 1994 Elsevier Science Ltd. All rights reserved.
• Studies on Polypeptides. XXXI. Synthetic Peptides Related to the N-Terminus of Bovine Pancreatic Ribonuclease (Positions 12-20)^1-4
  作者：Klaus Hofmann、Wilhelm Haas、Michael J. Smithers、Guido Zanetti

  DOI：10.1021/ja01081a041

  日期：1965.2