Z-Cys-OBzl | 86123-07-1

• 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: Z-Cys-OBzl
• 英文别名: benzyl (2R)-2-(phenylmethoxycarbonylamino)-3-sulfanylpropanoate
• CAS: 86123-07-1
• 化学式: C₁₈H₁₉NO₄S
• 分子量: 345.419
• InChiKey: SULMJWCLFZOLFC-INIZCTEOSA-N

物化性质

• 沸点：
  523.7±50.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  65.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-Cys-OBzl 在 碘 作用下， 以 甲醇 为溶剂， 反应 0.75h， 生成 N,N'-bis(benzyloxycarbonyl)-D-cystine dibenzyl ester
  参考文献：
  名称：

  2-氮丙啶羧酸的研究。X. 光学活性胱氨酸和threo-3,3'-二甲基胱氨酸的简单立体定向合成

  摘要：

  (2S)-Z-Azy-OBzl、(2S,3S)-Z-3-MeAzy-OBzl 及其对映异构体与 H2S 的反应通过立体特异性开环得到光学活性半胱氨酸和 thero-3-甲基半胱氨酸衍生物氮丙啶反应，随后的氧化和解封闭程序以良好的产率得到标题化合物。

  DOI：

  10.1246/bcsj.56.1565
• 作为产物：
  描述：

  benzyl (2R)-1-benzyloxycarbonyl-2-aziridinecarboxylate 在 三氟化硼乙醚 、 硫化氢 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 Z-Cys-OBzl
  参考文献：
  名称：

  2-氮丙啶羧酸的研究。X. 光学活性胱氨酸和threo-3,3'-二甲基胱氨酸的简单立体定向合成

  摘要：

  (2S)-Z-Azy-OBzl、(2S,3S)-Z-3-MeAzy-OBzl 及其对映异构体与 H2S 的反应通过立体特异性开环得到光学活性半胱氨酸和 thero-3-甲基半胱氨酸衍生物氮丙啶反应，随后的氧化和解封闭程序以良好的产率得到标题化合物。

  DOI：

  10.1246/bcsj.56.1565

文献信息

• Studies on 2-Aziridinecarboxylic Acid. IX. Convenient Synthesis of Optically Active<i>S</i>-Alkylcysteine,<i>threo</i>-<i>S</i>-Alkyl-β-methylcysteine, and Lanthionine Derivatives<i>via</i>the Ring-opening Reaction of Aziridine by Several Thiols
  作者：Kiichiro Nakajima、Hitomi Oda、Kenji Okawa

  DOI：10.1246/bcsj.56.520

  日期：1983.2

  and benzyl (2S,3S)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylate, and their enantiomers were treated with several thiols, and the corresponding S-alkylcysteine, threo-S-alkyl-β-methylcysteine, and lanthionine derivatives were prepared via the ring-opening reaction of aziridine in the presence of a catalytic amount of boron trifluoride etherate in good yields.

  已经研究了光学活性 S-烷基半胱氨酸、苏-S-烷基-β-甲基半胱氨酸和羊毛硫氨酸衍生物的方便合成。1-苄氧羰基-(2S)-2-氮丙啶羧酸苄酯和(2S,3S)-1-苄氧羰基-3-甲基-2-氮丙啶羧酸苄酯及其对映体用几种硫醇处理，相应的S-烷基半胱氨酸、苏- S-烷基-β-甲基半胱氨酸和羊毛硫氨酸衍生物通过氮丙啶在催化量的三氟化硼醚合物存在下的开环反应以良好的产率制备。
• Probing the Role of Polyphenol Oxidation in Mediating Insect−Pathogen Interactions. Galloyl-Derived Electrophilic Traps for the <i>Lymantria</i> <i>d</i><i>ispar</i> Nuclear Polyhedrosis Virus Matrix Protein Polyhedrin
  作者：Ken S. Feldman、Aruna Sambandam、Katherine E. Bowers、Heidi M. Appel

  DOI：10.1021/jo982477n

  日期：1999.8.1

  Galloyl-derived orthoquinone probes have been designed, synthesized, and utilized in an ongoing study of insect-pathogen interactions. A stable galloyl-derived orthoquinone O-methyl ether modified with both acidic and fluorescent appendages was successful in trapping the model nucleophile cysteine, a test protein bearing a single cysteine residue, and the viral occlusion body matrix protein polyhedrin from Lymantria dispar nuclear polyhedrosis virus (LdNPV), a pathogen of the gypsy moth caterpillar (GMc). This latter observation may be related to the molecular mechanism by which gallotannins decrease LdNPV infectivity in GMc's. Sufficient site isolation was not achieved with a polymer-bound reactive galloyl hydroxyorthoquinone electrophile to permit similar nucleophile trapping to compete with oligomerization.
• Ellagitannin Chemistry. The First Synthesis of Dehydrohexahydroxydiphenoate Esters from Oxidative Coupling of Unetherified Methyl Gallate
  作者：Stéphane Quideau、Ken S. Feldman

  DOI：10.1021/jo971354k

  日期：1997.12.1

  A simple o-chloranil-mediated oxidative dimerization of methyl gallate in anhydrous ether furnishes a dimethyl dehydrohexahydroxydiphenoate (DHHDP) product as a pale yellow precipitate in good yield. This methyl gallate dehydrodimer rapidly rearranges in acetone to give a mixture of two additional DHHDP regioisomers. One of these species corresponds to the isomer of the dehydrohexahydroxydiphenoyl group commonly observed in dehydroellagitannin natural products. Sodium dithionite-mediated reduction of the initially formed dimethyl dehydrohexahydroxydiphenoate and/or its derived regioisomers efficiently furnishes dimethyl hexahydroxydiphenoate (HHDP). Addition of N-(carbobenzyloxy)-L-cysteine benzyl ester to dimethyl dehydrohexahydroxydiphenoate(s) in THF solution produces two diastereomeric S-S-cysteinyl derivatives of dimethyl hexahydroxydiphenoate.
• Gerz, Manfred; Matter, Hans; Kessler, Horst, Angewandte Chemie, 1993, vol. 105, # 2, p. 311 - 313
  作者：Gerz, Manfred、Matter, Hans、Kessler, Horst

  DOI：——

  日期：——
• Galloyl-Derived Orthoquinones as Reactive Partners in Nucleophilic Additions and Diels−Alder Dimerizations:  A Novel Route to the Dehydrodigalloyl Linker Unit of Agrimoniin-Type Ellagitannins
  作者：Ken S. Feldman、Stéphane Quideau、Heidi M. Appel

  DOI：10.1021/jo961043u

  日期：1996.1.1

  Orthochloranil-mediated oxidation of galloyl monoethers furnishes the derived orthoquinones in excellent yield. These reactive electrophiles participate in a variety of nucleophilic addition reactions with heteroatomic and carbanionic partners. In addition, Lewis acid-mediated dimerization of the orthoquinones provides an efficient route to dehydrodigalloyl-type diaryl ether units characteristic of several ellagitannin natural products. The implications for ellagitannin biosynthesis and gallotannin-protein covalent attachment are discussed.