(S)-2-benzyloxycarbonylamino-3-(4-methoxy-1H-indol-3-yl)propionic acid | 406938-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-2-benzyloxycarbonylamino-3-(4-methoxy-1H-indol-3-yl)propionic acid
• 英文别名: Cbz-N-L-(4-OMe)Trp-OH；4-Methoxybenzyloxycarbonyl tryptophan；(2S)-3-(4-methoxy-1H-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 406938-51-0
• 化学式: C₂₀H₂₀N₂O₅
• 分子量: 368.389
• InChiKey: BBKWLZRRBGVYEP-INIZCTEOSA-N

物化性质

• 熔点：
  152 °C
• 沸点：
  643.8±55.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-benzyloxycarbonylamino-3-(4-methoxy-1H-indol-3-yl)propionic acid 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 N-Boc-D-AlaThz-Trp-(4-OMe)Trp-Gly-D-Abu-(Ph)Sec-Sar-OH
  参考文献：
  名称：

  Total Synthesis of the Cyclic Heptapeptide Argyrin B:  A New Potent Inhibitor of T-Cell Independent Antibody Formation

  摘要：

  [GRAPHICS]The total synthesis of Argyrin B (1) is presented using a synthetic plan that is convergent and flexible and conserves the stereogenic centers. The unusual amino acid 4-methoxy tryptophan (6) was obtained via an enzymatic resolution. Cyclization followed by oxidative elimination of the phenylseleno cysteine to the sensitive dehydroalanine afforded synthetic 1.

  DOI：

  10.1021/ol017184m
• 作为产物：
  描述：

  4-甲氧基芦竹碱 在 sodium hydroxide 、 青霉素(酰胺)酶 、 sodium ethanolate 、 碳酸氢钠 、 硫酸二甲酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 水 为溶剂， 反应 5.5h， 生成 (S)-2-benzyloxycarbonylamino-3-(4-methoxy-1H-indol-3-yl)propionic acid
  参考文献：
  名称：

  Total Synthesis of the Cyclic Peptide Argyrin B

  摘要：

  DOI：

  10.1002/1099-0690(200212)2002:23<3995::aid-ejoc3995>3.0.co;2-p

文献信息

• Method for Producing Intermediates for the Production of Novel Macrocycles that are Inhibitors of the Proteasomic Degradation of p27, such as Argyrin and Derivatives Thereof, and Uses of Said Macrocycles
  申请人：Kalesse Markus

  公开号：US20110311564A1

  公开（公告）日：2011-12-22

  The present invention relates to the use of particular macrocycles that are inhibitors of the proteasomic degradation of p27, in particular argyrin and derivatives thereof, for a treatment in a variety of conditions, such as the induction of immunotolerance, autoimmune diseases, bacterial infections, and proliferative diseases, such as cancers.

  本发明涉及使用特定的大环化合物，这些大环化合物是p27蛋白质降解的蛋白酶体抑制剂的抑制剂，尤其是精胺及其衍生物，用于治疗多种病症，如诱导免疫耐受、自身免疫疾病、细菌感染以及增殖性疾病，如癌症。
• Method for producing intermediates for the production of novel macrocycles that are inhibitors of the proteasomic degradation of p27, such as argyrin and derivatives thereof, and uses of said macrocycles
  申请人：Helmholtz-Zentrum für Infektionsforschung GmbH

  公开号：EP2138507A1

  公开（公告）日：2009-12-30

  The present invention relates to the use of particular macrocycles that are inhibitors of the proteasomic degradation of p27, in particular argyrin and derivatives thereof, for a treatment in a variety of conditions, such as the induction of immunotolerance, autoimmune diseases, bacterial infections, and proliferative diseases, such as cancers.

  本发明涉及使用特定的宏环化合物，如阿吉林及其衍生物，作为p27蛋白酶解抑制剂，用于治疗各种疾病，例如诱导免疫耐受性、自身免疫疾病、细菌感染和增殖性疾病，如癌症。
• Total Synthesis of the Cyclic Heptapeptide Argyrin B:  A New Potent Inhibitor of T-Cell Independent Antibody Formation
  作者：Steven V. Ley、Alain Priour、Christoph Heusser

  DOI：10.1021/ol017184m

  日期：2002.3.1

  [GRAPHICS]The total synthesis of Argyrin B (1) is presented using a synthetic plan that is convergent and flexible and conserves the stereogenic centers. The unusual amino acid 4-methoxy tryptophan (6) was obtained via an enzymatic resolution. Cyclization followed by oxidative elimination of the phenylseleno cysteine to the sensitive dehydroalanine afforded synthetic 1.
• METHOD FOR PRODUCING INTERMEDIATES FOR THE PRODUCTION OF NOVEL MACROCYCLES THAT ARE INHIBITORS OF THE PROTEASOMIC DEGRADATION OF P27, SUCH AS ARGYRIN AND DERIVATIVES THEREOF, AND USES OF SAID MACROCYCLES
  申请人：Helmholtz-Zentrum für Infektionsforschung GmbH

  公开号：EP2303916B1

  公开（公告）日：2012-05-09
• US9458200B2
  申请人：——

  公开号：US9458200B2

  公开（公告）日：2016-10-04