N-benzoyl-L-glutamic acid γ-methyl ester | 14307-84-7

• 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-benzoyl-L-glutamic acid γ-methyl ester
• 英文别名: (S)-2-benzamido-5-methoxy-5-oxopentanoic acid；Bz-Glu(γ-OMe)-OH；Bz-Glu(γ-OMe)；N-benzoyl-L-glutamic acid-5-methyl ester；N-Benzoyl-L-glutaminsaeure-5-methylester；N-Benzoylglutaminsaeure-γ-methylester；(2S)-2-benzamido-5-methoxy-5-oxopentanoic acid
• CAS: 14307-84-7
• 化学式: C₁₃H₁₅NO₅
• 分子量: 265.266
• InChiKey: ZOCDRUFCMFNIKQ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzoyl-L-glutamic acid γ-methyl ester 在 4-二甲氨基吡啶 、 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 4-benzoylamino-5-oxo-hexanoic acid
  参考文献：
  名称：

  Lepschy,J. et al., Justus Liebigs Annalen der Chemie, 1974, p. 1753 - 1762

  摘要：

  DOI：
• 作为产物：
  描述：

  N-Benzoyl-glutaminsaeure-diethylester 在 盐酸 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 N-benzoyl-L-glutamic acid γ-methyl ester
  参考文献：
  名称：

  一种用于捕获维生素K依赖性羧化酶的γ-谷氨酰基自由基中间体的方法：α，β-亚甲基谷氨酸。

  摘要：

  维生素K依赖性羧化酶通过产生γ-谷氨酰基自由基，γ-谷氨酰基碳负离子或通过协同的羧化作用激活底物肽的谷氨酰胺γ-CH进行羧化。我们建议通过包含谷氨酸的α，β-环丙烷类似物的底物的分子内重排来拦截推定的γ-谷氨酰胺基自由基。环丙基羰基自由基重排成2-丁烯基自由基是快速，放热的，并被认为可诊断自由基的形成。谷氨酸的β-环丙烷类似物1-氨基-2-（羧甲基）环丙烷-1-甲酸酯是从α-酮戊二酸二乙酯开始合成的。首先用苄腈在硫酸中处理α-酮酯，得到α，α-二苯甲酰胺基戊二酸二乙酯。字母 在对苯磺酸在热苯中处理后，将α-二苯甲酰胺酸裂解生成α，β-脱氢氨基酸和苯甲酰胺。将重氮甲烷加到脱氢氨基酸中导致重氮甲烷的环加成和吡唑啉的生成，其在辐射下损失了N 2，得到了被保护的含环丙烷的氨基酸类似物。N-苯甲酰基-α，β-亚甲基谷氨酸二乙酯的酸性水解导致高产率地产生未保护的氨基酸，α，β-亚甲基谷氨酸。在该合成中

  DOI：

  10.1021/jm00164a056

文献信息

• Generation of Oxyphosphonium Ions by Photoredox/Cobaloxime Catalysis for Scalable Amide and Peptide Synthesis in Batch and Continuous‐Flow
  作者：Junqi Su、Jia‐Nan Mo、Xiangyang Chen、Alexander Umanzor、Zheng Zhang、Kendall N. Houk、Jiannan Zhao

  DOI：10.1002/anie.202112668

  日期：2022.1.26

  for the synthesis of amides and peptides is reported. Synergistic cooperation between a cobaloxime and a photoredox catalyst removes the elements of H2O through the use of PPh3 as a gentle organic reductant. The deoxygenative method is compatible with gram-scale peptide synthesis and applicable to peptide fragment condensation and SPPS, which may find applications in both organic synthesis and pharmaceutical

  报道了一种用于合成酰胺和肽的光催化方法。钴肟和光氧化还原催化剂之间的协同作用通过使用 PPh 3作为温和的有机还原剂去除了 H 2 O 元素。脱氧方法与克级肽合成兼容，适用于肽片段缩合和SPPS，可在有机合成和药物生产中找到应用。
• Discovery of novel chemical scaffolds as RhoA inhibitors using virtual screening, synthesis, and bioactivity evaluation
  作者：Chao Zhang、Hui-Jie Wang、Qi-Chao Bao、Jin-Lei Bian、Ying-Rui Yang、Qi-Dong You、Xiao-Li Xu

  DOI：10.1039/c6ra11398b

  日期：——

  RhoA has been implicated in diverse cellular functions and is a potential cancer therapeutic target.

  RhoA已被涉及到多种细胞功能，并且是潜在的癌症治疗靶点。
• The demonstration of selective peptide bond formation in clear aqueous solutions
  作者：Darshan Ranganathan、Girij Pal Singh

  DOI：10.1039/c39900000142

  日期：——

  The distribution of dipeptides upon treatment of equimolar amounts of glutamic acid, leucine, and C6H11NCN(CH2)3+NMe3–OSO2C6H4Me-p, in clear aqueous solution followed by N, C-protection, was found to be: Bz-Glu(γ-OMe)-Leu-OMe (72%), Bz-Glu(α-OMe)-Glu-di-OMe (15%), and Bz-Leu-Leu-OMe (8%); Bz-Leu-Glu-di-OMe, Bz-Glu(α-OMe)-Leu-OMe, and Bz-Glu(γ-OMe)Glu-di-OMe could not be detected (Bz = PhCO).

  二肽的处理时的等摩尔量的谷氨酸，亮氨酸，和C的分布6 ħ 11 Ñ Ç N（CH 2）3 + NME 3 - OSO 2 C ^ 6 ħ 4 ME- p，在透明的水性溶液，接着Ñ，发现C保护是：Bz-Glu（γ-OMe）-Leu-OMe（72％），Bz-Glu（α-OMe）-Glu-di-OMe（15％）和Bz-Leu- Leu-OMe（8％）；无法检测到Bz-Leu-Glu-di-OMe，Bz-Glu（α-OMe）-Leu-OMe和Bz-Glu（γ-OMe）Glu-di-OMe（Bz = PhCO）。
• Protein Backbone Modification by Novel C.alpha.-C Side-Chain Scission
  作者：Darshan Ranganathan、Narendra K. Vaish、Kavita Shah

  DOI：10.1021/ja00094a008

  日期：1994.7

  alpha-Ketoamide (-NH-CO-CO-) units in intact peptides are generated from Ser/Thr residues via Ru(VIII)catalyzed C-alpha-C side-chain scission. Facets associated with this novel cu-carbon modification have been probed with 75 peptides chosen to represent every possible peptide environment. The reactions were carried out at room temperature with in situ generated Ru(VIII) in biphasic (CH3CN/CCl4/pH 3 phosphate buffer, 1:1:2 v/v) medium. Whereas Ser/Thr residues placed at the C-terminal end in peptides undergo N-C bond scission leading to des-Ser/Thr peptide amides-thus acting as Gly equivalents in simulating the alpha-amidating action of pituitary enzymes-those located at the N-terminal or nonterminal or even at the C-terminal position (protected as amide) were found to undergo oxidative C-C bond scission (involving C-alpha and C side-chain bond), resulting in the generation of alpha-ketoamide (-NH-CO-CO-) units in the intact peptide backbone. The difference in the products arising from C-alpha-C side-chain scission of Ser/Thr esters and amides is rationalized on the basis of a common mechanism involving either oxaloesters [Pep-NH-CO-COX; X = OMe] or oxalamides [X = NH2 or NH-Pep] arising from the oxidation of initially formed carbinolamide intermediates [Pep-NH-CH(OH)-COX],wherein, while the former are shown to undergo hydrolysis to terminal amides [Pep-NH2], the oxalamides are found to be stable to hydrolysis. Ancillary noteworthy findings are those of peptide bond scission when contiguous Ser-Ser/Thr-Thr residues are present and the oxidative cleavage at C-terminal Tyr/Trp sites generating des amides. The oxidative methodology presented here is mild, simple, and practical and proceeds with chiral retention. The insensitivity of a large number of amino acid residues, such as Gly, Ala, Leu, Asn, Gln, Asp, Glu, Pro, Arg, Phe, Lys, Val, and Aib, and N-protecting groups, such as Boc, Z, and Bz, toward Ru(VIII) under the experimental conditions should make this methodology practical and useful. Sulfur-containing amino acids Cys and Met get oxidized to sulfones in the products.
• Direct Acylation of α-Amino Acids and Dipeptides
  作者：Edward Ronwin

  DOI：10.1021/jo50017a014

  日期：1953.11