N,N-phthaloyl-L-methionine | 162366-20-3

• 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: N,N-phthaloyl-L-methionine
• 英文别名: N-phthaloyl-D-methionine；(R)-2-(1,3-dioxoisoindolin-2-yl)-4-(methylthio)butanoic acid；(2R)-2-(1,3-dioxoisoindol-2-yl)-4-methylsulfanylbutanoic acid
• CAS: 162366-20-3
• 化学式: C₁₃H₁₃NO₄S
• 分子量: 279.317
• InChiKey: VMTKJVHNTIEOCU-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 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：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-phthaloyl-L-methionine 在 双氧水 作用下， 以 甲醇 为溶剂， 生成 (R_C)-N-phthaloylmethionine sulfoxide
  参考文献：
  名称：

  PEPTIDE ANALOGUES

  摘要：

  本发明涉及式（I）化合物及其药用可接受盐，其中取代基如本文所述，并且它们在医学上的用途，特别是作为阿片受体激动剂。

  公开号：

  US20110207654A1
• 作为产物：
  描述：

  D-蛋氨酸 、 N-乙氧羰基邻苯二甲酰亚胺 在 sodium carbonate 作用下， 以 水 为溶剂， 反应 5.0h， 生成 N,N-phthaloyl-L-methionine
  参考文献：
  名称：

  用于确定α-氨基酸衍生物绝对构型的手性传感器

  摘要：

  通过比较在（R）-CSA 1和（S）存在下N-邻苯二甲酰基保护的α-氨基酸的α氢的质子NMR化学位移值，开发了一种简单的α-氨基酸构型分配策略-CSA 1。可以在NMR管中直接在手性溶剂化剂与N-邻苯二甲酰基保护的α-氨基酸的混合溶液上获得高分辨的NMR光谱，从而给出可明显区分的质子信号而不会产生干扰，从而显着提高了分配的准确性并加快了分配过程。该策略广泛适用于各种天然和非天然氨基酸。

  DOI：

  10.1039/c8ob01933a

文献信息

• Intramolecular carbenoid ylide forming reactions of 2-diazo-3-keto-4-phthalimidocarboxylic esters derived from methionine and cysteine
  作者：Marc Enßle、Stefan Buck、Roland Werz、Gerhard Maas

  DOI：10.3762/bjoc.8.49

  日期：——

  three steps. Upon rhodium-catalysed dediazoniation, two intramolecular carbenoid reactions competed, namely the formation of a cyclic sulfonium ylide and that of a six-ring carbonyl ylide. The S-methyl and S-benzyl ylides 12a and b could be isolated, while S-allyl ylide 12c underwent a [2,3]-sigmatropic rearrangement. The short-lived carbonyl ylides derived from methionine and S-benzylcysteine formed head-to-tail

  蛋氨酸、S-苄基半胱氨酸和S-烯丙基半胱氨酸分三步转化为2-重氮-3-氧代-4-邻苯二甲酰亚胺甲酸酯8a-c。在铑催化的脱重氮反应中，两个分子内类胡萝卜素反应竞争，即形成环状锍叶立德和六环羰基叶立德。可以分离S-甲基和S-苄基叶立德12a和b，而S-烯丙基叶立德12c经历[2,3]-σ重排。由甲硫氨酸和 S-苄基半胱氨酸衍生的短寿命羰基叶立德通过 [3 + 3]-环加成形成头尾二聚体，并且可以被外部亲偶极试剂捕获，而 S-烯丙基衍生物 14c 通过以下方式产生五环化合物 17分子内[3 + 2]-环加成反应。
• Peptide analogues
  申请人：Barber Christopher Gordon

  公开号：US08598123B2

  公开（公告）日：2013-12-03

  The present invention relates to compounds of Formula (I) and their pharmaceutically acceptable salts, wherein the substituents are as described herein, and their use in medicine, in particular as opioid agonists.

  本发明涉及公式（I）化合物及其药学上可接受的盐，其中取代基如本文所述，并且它们在医学上的用途，特别是作为阿片类受体激动剂。
• 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.
• 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.
• TAKEUCHI, TOYOHIDE;NIWA, TAKEO;ISHII, DAIDO, J. CHROMATOGR., 407,(1987) 141-150
  作者：TAKEUCHI, TOYOHIDE、NIWA, TAKEO、ISHII, DAIDO

  DOI：——

  日期：——