(S_SS_C)-N-phthaloylmethionine sulfoxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (S_SS_C)-N-phthaloylmethionine sulfoxide
• 英文别名: (2S)-2-(1,3-dioxoisoindol-2-yl)-4-[(S)-methylsulfinyl]butanoic acid
• 化学式: C₁₃H₁₃NO₅S
• 分子量: 295.316
• InChiKey: QYXFLPXRIFFGJI-FVINQWEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S_SS_C)-N-phthaloylmethionine sulfoxide 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以72%的产率得到(S_CS_S)-L-methionine sulfoxide
  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
• 作为产物：
  描述：

  (alphaS)-1,3-二氢-alpha-[2-(甲硫基)乙基]-1,3-二氧代-2H-异吲哚-2-乙酸 在 Beauveria Bassiana ATCC 7159 、 氧气 作用下， 反应 48.0h， 以60%的产率得到(S_SS_C)-N-phthaloylmethionine sulfoxide
  参考文献：
  名称：

  Biocatalytic and chemical preparation of all four diastereomers of methionine sulfoxide

  摘要：

  Biocatalytic or chemical oxidations can be used in a complementary manner for the preparation of all four diastereomers of methionine sulfoxide with high diastereomeric purity in overall isolated yields of 20-55% from methionine. The N-phthaloyl derivatives of L-and D-methionine were selectively oxidised to the (SSSC) and (SSRC) sulfoxides respectively by biotransformation using the fungus Beauveria bassiana ATCC 7159. Hydrogen peroxide oxidation of the same materials gave mixtures from which the. (SSSC) land (RSRC) isomers can be readily isolated by crystallisation. Chromatography of the residual material then afforded the (RSSC) and (SSRC)-isomers. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00042-1

文献信息

• Biocatalytic and chemical preparation of all four diastereomers of methionine sulfoxide
  作者：Herbert L. Holland、Frances M. Brown

  DOI：10.1016/s0957-4166(98)00042-1

  日期：1998.2

  Biocatalytic or chemical oxidations can be used in a complementary manner for the preparation of all four diastereomers of methionine sulfoxide with high diastereomeric purity in overall isolated yields of 20-55% from methionine. The N-phthaloyl derivatives of L-and D-methionine were selectively oxidised to the (SSSC) and (SSRC) sulfoxides respectively by biotransformation using the fungus Beauveria bassiana ATCC 7159. Hydrogen peroxide oxidation of the same materials gave mixtures from which the. (SSSC) land (RSRC) isomers can be readily isolated by crystallisation. Chromatography of the residual material then afforded the (RSSC) and (SSRC)-isomers. (C) 1998 Elsevier Science Ltd. All rights reserved.
• 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.