γ-OBzl-L-Glu-α-OMe | 57584-59-5

• 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: γ-OBzl-L-Glu-α-OMe
• 英文别名: L-Glu(OBn)-OMe；benzyl methyl γ-glutamate；γ-benzyl glutamic acid methyl ester；Glu(O-Bzl)-OMe；5-Benzyl 1-methyl L-glutamate；5-O-benzyl 1-O-methyl (2S)-2-aminopentanedioate
• CAS: 57584-59-5
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: BINSDCQBEWYNGL-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  γ-OBzl-L-Glu-α-OMe 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 1,1,3,3-四甲基脲 、 tin(ll) chloride 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 -L-glutamic acid 1-methyl 5-benzyl diester
  参考文献：
  名称：

  Studies on Selectin Blockers. 7. Structure−Activity Relationships of Sialyl Lewis X Mimetics Based on Modified Ser-Glu Dipeptides

  摘要：

  We have previously found that heterochiral fucodipeptides, L-Ser-D-Glu (3a) and D-Ser-L-Glu (3b), exhibited up to 20-100 times more potency than a sialyl Lewis X (sLe(x), 1) and a 3'-sulfated Lewis X analogue (2) toward E-selectin binding and have also proposed, from molecular dynamics calculation, that their strong activities would depend on a possible formation of the type II and/or type II' beta-turn of compounds 3a,b (Tsukida, T.; Hiramatsu, Y.; Tsujishita, H.; Kiyoi, T.; Yoshida, M.; Kurokawa, K.; Moriyama, H.; Ohmoto, H.; Wada, Y.; Saito, T.; Kondo, H. J. Med. Chem. 1997, 40, 3534-3541). To clarify our hypothesis, we synthesized several analogues of compounds 3a,b and investigated their structure-activity relationships. As a result, it was indicated that the type II and/or type II' beta-turn conformation would be a comparatively tight form and would play important roles in favorable binding to E-selectin. These findings indicate that sLe(x) mimetics with type II and type II'-beta-turn dipeptides could be a useful methodology for the design of an active selectin blocker.

  DOI：

  10.1021/jm980267x
• 作为产物：
  描述：

  Boc-L-谷氨酸5苄酯Alpha甲酯 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 γ-OBzl-L-Glu-α-OMe
  参考文献：
  名称：

  含色氨酸肽的铁催化仿生二聚化

  摘要：

  八羧基酞菁铁络合物催化的色氨酸衍生物的仿生氧化二聚反应是在水性介质中以氧作为本体氧化剂建立的。该协议允许对具有显着功能组耐受性的各种含色氨酸肽进行二聚化，以构建天然和非天然的吡咯并吲哚二聚体和二聚化肽，并具有连接两个转弯结构的独特支架。

  DOI：

  10.1002/anie.202302404

文献信息

• Improved Auxiliary for the Synthesis of Medium-Sized Bis(lactams)
  作者：Jasper Springer、T. Paul Jansen、Steen Ingemann、Henk Hiemstra、Jan H. van Maarseveen

  DOI：10.1002/ejoc.200700832

  日期：2008.1

  Our auxiliary-based method for the synthesis of bis(lactams) has been optimized. A novel auxiliary is described that is inserted in the backbone of a linear peptide facilitating the mutually reactive terminal groups to approach one another for a cyclization reaction. A subsequent ring contraction mechanism leads to the bis(lactams) with the remainings of the auxiliary still attached. Functionalized seven-

  我们基于辅助的双（内酰胺）合成方法已得到优化。描述了一种新型辅助剂，其插入线性肽的骨架中，促进相互反应的末端基团相互接近以进行环化反应。随后的环收缩机制导致双（内酰胺）与辅助剂的剩余部分仍然连接。已经制备了使用传统方法难以获得的功能化的七元和八元双（内酰胺）。从双（内酰胺）中去除助剂已经描述了可能发生的副反应。
• Tetrapeptide Copper Catalysts Capable Of Oxidizing Hydrocarbons At Room Temperature
  申请人：University of the West Indies, a Regional Institution, established by Royal Charter

  公开号：US20160060292A1

  公开（公告）日：2016-03-03

  The present invention relates to peptide copper catalysts capable of oxidizing hydrocarbons at room temperature.

  本发明涉及能够在室温下氧化烃的肽铜催化剂。
• Selective Ester-exchange Reactions of Dibenzyl-aspartate and -glutamate in the Coordination Sphere of Copper(II) Ion
  作者：Yasuo Nakao、Masaaki Demichi、Akitsugu Nakahara

  DOI：10.1246/bcsj.53.1564

  日期：1980.6

  in methanol for 30 min, bis(α-methyl β-benzyl N-salicylideneaspartato)copper(II) and bis(α-methyl γ-benzyl N-salicylideneglutamato)copper(II) were obtained. The mechanism of these selective ester-exchange reactions in the metal-coordination sphere has been discussed. Several Schiff bases were obtained and characterized.

  首次制备了由水杨醛和天冬氨酸或谷氨酸二苄基酯衍生的席夫碱的铜 (II) 配合物。将这些配合物在甲醇中的溶液回流 30 分钟后，得到双（α-甲基 β-苄基 N-水杨亚基）铜（II）和双（α-甲基 γ-苄基 N-水杨基谷氨酸）铜（II）。已经讨论了金属配位领域中这些选择性酯交换反应的机制。获得并表征了几种席夫碱。
• Carboxylic Anhydride Synthesis from γ-Benzyl-<scp>l</scp>-glutamate and Dimethyl Carbonate
  作者：Zhao Zhang、Kunmei Su、Zhenhuan Li

  DOI：10.1021/acs.orglett.8b03984

  日期：2019.2.1

  A green, environmentally friendly, and nontoxic method was developed to synthesize carboxylic anhydrides (NCAs) from γ-benzyl-l-glutamate (BLG) and dimethyl carbonate (DMC) though two steps: synthesis of N-methoxycarbonyl-γ-benzyl-l-glutamate intermediate (NOM-BLG) and cyclization. The highest yields of NOM-BLG (up to 83.7%) and NCA-BLG (up to 66.7%) were obtained. Most importantly, the use of DMC

  绿色，环保，和无毒的方法被开发用于合成从γ苄基羧酸酐（种NCA）升-谷氨酸（BLG）和碳酸二甲酯（DMC），尽管两个步骤：合成Ñ甲氧基羰基γ苄基升-谷氨酸中间体（NOM-BLG）和环化。获得最高产量的NOM-BLG（高达83.7％）和NCA-BLG（高达66.7％）。最重要的是，DMC的使用将为合成NCA打开一扇创新之门。
• Synthesis of maleimide-braced peptide macrocycles and their potential anti-SARS-CoV-2 mechanisms
  作者：Jian Li、Jina Sun、Xianglei Zhang、Ruxue Zhang、Qian Wang、Lin Wang、Leike Zhang、Xiong Xie、Chunpu Li、Yu Zhou、Jiang Wang、Gengfu Xiao、Fang Bai、Hong Liu

  DOI：10.1039/d2cc06371a

  日期：——

  A novel strategy to construct maleimide-braced macrocycles has been established. The unique macrocycles exhibited excellent anti-SARS-CoV-2 infection activity via targeting the N protein of SARS-CoV-2.

  一种构建马来酰亚胺支撑的大环的新策略已经建立。这些独特的大环通过针对SARS-CoV-2的N蛋白表现出了出色的抗SARS-CoV-2感染活性。