1-苄基5-(2,5-二氧代-1-吡咯烷基)N-{[(2-甲基-2-丙基)氧基]羰基}-L-谷氨酸 | 78658-49-8

• 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
• 中文名称: 1-苄基5-(2,5-二氧代-1-吡咯烷基)N-{[(2-甲基-2-丙基)氧基]羰基}-L-谷氨酸
• 英文名称: Boc-Glu(OSu)-OBn
• 英文别名: Boc-glu(osu)-obzl；1-O-benzyl 5-O-(2,5-dioxopyrrolidin-1-yl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate
• CAS: 78658-49-8
• 化学式: C₂₁H₂₆N₂O₈
• 分子量: 434.446
• InChiKey: UZVYXLRCVBQZNV-HNNXBMFYSA-N

物化性质

• 熔点：
  147-150 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-苄基5-(2,5-二氧代-1-吡咯烷基)N-{[(2-甲基-2-丙基)氧基]羰基}-L-谷氨酸 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以84%的产率得到benzyl (S)-2-((tert-butoxycarbonyl)amino)-5-hydroxypentanoate
  参考文献：
  名称：

  方便合成L-脯氨酸苄酯。

  摘要：

  当暴露于水性缓冲液中时，δ-羟基-L-正缬氨酸酯的甲磺酸酯或甲苯磺酸酯自发产生L-脯氨酸酯。这种新颖的反应导致了开发光学活性脯氨酸酯的简单途径。

  DOI：

  10.1016/s0960-894x(99)00546-6
• 作为产物：
  描述：

  丁二酰亚胺 、 N-叔丁氧羰基-L-谷氨酸 1-苄酯 在 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 生成 1-苄基5-(2,5-二氧代-1-吡咯烷基)N-{[(2-甲基-2-丙基)氧基]羰基}-L-谷氨酸
  参考文献：
  名称：

  Synthesis of the major component of alamethicin

  摘要：

  DOI：

  10.1021/ja00411a018

文献信息

• Application of the Thioacid-Azide Ligation (TAL) for the Preparation of Glycosylated and Fluorescently Labeled Amino Acids
  作者：Katja Rohmer、Jamsad Mannuthodikayil、Valentin Wittmann

  DOI：10.1002/ijch.201500001

  日期：2015.4

  and dansylated amino acids is reported. 2‐Azidosulfonylethyl glycosides were prepared from peracetylated monosaccharides and reacted with thioacid‐containing derivatives of aspartic acid and glutamic acid. Likewise, aromatic sulfonyl azides were employed. Ligation products were obtained in yields of up to 96 %. Different conditions for the generation of the thioacids were compared. Whereas reaction

  硫代羧酸与叠氮化物的反应（硫代酸-叠氮化物连接，TAL）是一种化学选择性转化，导致形成酰胺键。尤其是在缺乏电子的磺酰叠氮的情况下，在室温下几分钟之内，在各种溶剂中，反应均以优异的收率发生。在本文中，报道了TAL在合成糖基化和丹酰基化氨基酸中的应用。由过乙酰化的单糖制备2-叠氮磺酰基乙基糖苷，并使其与含硫酸的天冬氨酸和谷氨酸衍生物反应。同样，使用芳族磺酰叠氮化物。连接产物的产率高达96％。比较了产生硫代酸的不同条件。通过温和的酸解原位制备硫代酸。
• Amino acids and peptides. XXVII. Synthesis of phytochelatin-related peptides and examination of their heavy metal-binding properties.
  作者：Yoshikazu MATSUMOTO、Yoshio OKADA、Kyong-Son MIN、Satomi ONOSAKA、Keiichi Tanaka

  DOI：10.1248/cpb.38.2364

  日期：——

  Phytochelatin (PC)-related peptides were prepared by a conventional solution method and their heavy metal-binding properties were examined. Different from the Cu2+ and Cu+ -binding properties of metallothionein (MT)-related peptides, the Cu2+ and Cu+ -binding properties of PC-related peptides were fairly dependent on structure. It is of interest that gamma-Glu-Cys-Gly (glutathione) exhibited quite

  通过常规溶液法制备植物螯合素（PC）相关肽，并检查其重金属结合特性。与金属硫蛋白（MT）相关肽的Cu2 +和Cu +结合特性不同，PC相关肽的Cu2 +和Cu +结合特性完全取决于结构。有趣的是，γ-Glu-Cys-Gly（谷胱甘肽）表现出与其他PC相关肽完全不同的Cu2 +和Cu +结合特性，其结合能力与MT相关肽相当。谷胱甘肽的Cd2 +结合特性与Cys相似，PC相关肽的Cd2 +结合能力与γ-Glu-Cys肽单元的增加成比例地增加。
• Convenient synthesis of benzyl ester
  作者：Armando Córdova、Neal N. Reed、Jon A. Ashley、Kim D. Janda

  DOI：10.1016/s0960-894x(99)00546-6

  日期：1999.11

  Mesylates or tosylates of delta-hydroxy-L-norvaline esters spontaneously afford L-proline esters upon exposure to aqueous buffer in near quantitative yield. This novel reaction has led to the development of a simple route to optically active proline esters.

  当暴露于水性缓冲液中时，δ-羟基-L-正缬氨酸酯的甲磺酸酯或甲苯磺酸酯自发产生L-脯氨酸酯。这种新颖的反应导致了开发光学活性脯氨酸酯的简单途径。
• Concise Synthesis of Enantiomerically Pure Phenylalanine, Homophenylalanine, and Bishomophenylalanine Derivatives Using Organozinc Chemistry:  NMR Studies of Amino Acid-Derived Organozinc Reagents
  作者：Richard F. W. Jackson、Rebecca J. Moore、Charles S. Dexter、Jason Elliott、Charles E. Mowbray

  DOI：10.1021/jo981133u

  日期：1998.10.1

  Protected phenylalanines 23 (seven examples), homophenylalanines 7 (eight examples), and bishomophenylalanines 8 (seven examples) have been prepared by palladium-catalyzed coupling of the amino acid-derived organozinc reagents 13, 5, and 6, respectively, with aryl iodides. While the reactions of the zinc reagent 13 may be conducted in both THF and DMF as solvent, the results obtained in DMF are generally superior. In the case of the reagents 5 and 6 the results are far superior in DMF. NMR investigations on the structure of the zinc reagents 13 in THF suggest that there is strong intramolecular coordination of the urethane carbonyl group, whereas in DMF this interaction is completely suppressed.
• Synthesis of the major component of alamethicin
  作者：B. F. Gisin、D. G. Davis、Z. K. Borowska、J. E. Hall、S. Kobayashi

  DOI：10.1021/ja00411a018

  日期：1981.10