(R_SR_C)-N-phthaloylethionine sulfoxide | 251364-88-2

• 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: (R_SR_C)-N-phthaloylethionine sulfoxide
• CAS: 251364-88-2
• 化学式: C₁₄H₁₅NO₅S
• 分子量: 309.343
• InChiKey: PJAMTSYBVUZCHX-WSVYEEACSA-N

反应信息

• 作为反应物：
  描述：

  (R_SR_C)-N-phthaloylethionine sulfoxide 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (R_SR_C)-ethionine 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：

  N-phthaloyl-D-ethionine 在 双氧水 作用下， 以 甲醇 为溶剂， 以0.4 g的产率得到(R_SR_C)-N-phthaloylethionine 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