Glu-Pro | 41745-47-5

• 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: Glu-Pro
• 英文别名: glutamyl-proline；(2S)-1-[(2S)-2-amino-4-carboxybutanoyl]pyrrolidine-2-carboxylic acid
• CAS: 41745-47-5
• 化学式: C₁₀H₁₆N₂O₅
• 分子量: 244.247
• InChiKey: YBTCBQBIJKGSJP-BQBZGAKWSA-N

物化性质

• 沸点：
  558.1±50.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  可得然胶 、 Glu-Pro 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.33h， 生成 N-(β-D-deoxyfructos-1-yl)-α-glutamyl-L-proline
  参考文献：
  名称：

  N-（β-d-脱氧果糖-1-基）-1-谷氨酸和N-（β-d-脱氧果糖-1-基）-β-丙氨酰基-1-组氨酸的美拉德模拟食品级合成冻干和热处理的过程。

  摘要：

  谷氨酸的典型糖缀合物，即ñ - （β- d -deoxyfructos -1-基） -升用食品级制备方法成功合成了β-谷氨酸作为主要异构体，收率为96.08％，其化学结构已通过质谱和1D / 2D NMR明确证实。系统地研究了葡萄糖和谷氨酸的反应动力学，以研究冻干和热处理对反应物转化为相应的Amadori重排产物（ARP）的影响。有趣的是，除了初始的pH值，温度和加热时间外，谷氨酸的初始浓度还影响了最终的收率，因为分子内的脱水同时发生，与美拉德反应和降解反应竞争。此外，还以约66的产率制备了类似的肌肽的Amadori化合物。条件优化后，收率可达38％，收率可进一步提高到95％。确认该肽的相应ARP的一种主要异构体是通过结构表征获得N-（β- d-脱氧果糖-1-基）-β-丙氨酰基-1-组氨酸，表明这是制备N-（β- d-脱氧果糖-1-基）-氨基的良好方法酸/肽。

  DOI：

  10.1021/acs.jafc.0c03009
• 作为产物：
  描述：

  在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 Glu-Pro
  参考文献：
  名称：

  Functional Identification and Structure Determination of Two Novel Prolidases from cog1228 in the Amidohydrolase Superfamily,

  摘要：

  Two uncharacterized enzymes from the amidohydrolase superfamily belonging to cog1228 were cloned, expressed, and purified to homogeneity. The two proteins, Sgx9260c (gi|44242006) and Sgx9260b (gi|44479596), were derived from environmental DNA samples originating from the Sargasso Sea. The catalytic function and substrate profiles for Sgx9260c and Sgx9260b were determined using a comprehensive library of dipeptides and N-acyl derivative of L-amino acids. Sgx9260c catalyzes the hydrolysis of Gly-L-Pro, L-Ala-L-Pro, and N-acyl derivatives of L-Pro. The best substrate identified to date is N-acetyl-L-Pro with a value of k(cat)/K-m of 3 x 10(5) M-1 s(-1). Sgx9260b catalyzes the hydrolysis of L-hydrophobic L-Pro dipeptides and N-acyl derivatives of L-Pro. The best substrate identified to date is N-propionyl-L-Pro with a value of k(cat)/K-m of 1 x 10(5) M-1 s(-1). Three-dimensional structures of both proteins were determined by X-ray diffraction methods (PDB codes 3MKV and 3FEQ). These proteins fold as distorted (beta/alpha)(8)-barrels with two divalent cations in the active site. The structure of Sgx9260c was also determined as a complex with the N-methylphosphonate derivative of L-Pro (PDB code 3N2C). In this structure the phosphonate moiety bridges the binuclear metal center, and one oxygen atom interacts with His-140. The a-carboxylate of the inhibitor interacts with Tyr-231. The proline side chain occupies a small substrate binding cavity formed by residues contributed from the loop that follows beta-strand 7 within the (beta/alpha)(8)-barrel. A total of 38 other proteins from cog1228 are predicted to have the same substrate profile based on conservation of the substrate binding residues. The structure of an evolutionarily related protein, Cc2672 from Caulobacter crecentus, was determined as a complex with the N-methylphosphonate derivative of L-arginine (PDB code 3MTW).

  DOI：

  10.1021/bi100897u

文献信息

• N-carboxyalkyl dipeptides, a process for preparing and a pharmaceutical composition comprising the same
  申请人：Merck & Co., Inc.

  公开号：EP0049506A1

  公开（公告）日：1982-04-14

  N-Carboxyalkyl dipeptides and derivatives thereof are disclosed which are useful as angiotensin converting enzyme inhibitors and as antihypertensives, and a process for preparing them. Those compounds are represented by the formula wherein R and R5 are individually hydroxy, lower alkoxy, aralkoxy; R1 is C1-8 alkyl; substituted C1-5 alkyl, substituted aralkyl or substituted heteroaralkyl; R2 is hydroxy, amino, alkoxy, aralkyloxy; n is one, two or three; R3 is aryl, heteroaryl, cycloalkyl, aminoloweralkyl, aralkyl; R4 is hydrogen or loweralkyl; or R3 and R4 are joined to form a ring having the following formulae: R6 is hydrogen or loweralkyl; p is 1, 2, or 3; W is a bond, -CH2-, or C=O; and, Z is a bond, -CH2-, or -CH2CH2-; and, the pharmaceutically acceptable salts thereof.

  本发明公开了可用作血管紧张素转换酶抑制剂和抗高血压药的 N-羧烷基二肽及其衍生物，以及制备它们的工艺。 这些化合物用式表示 式中 R 和 R5 分别为羟基、低级烷氧基、烷氧基； R1 是 C1-8 烷基、取代的 C1-5 烷基、取代的芳基或取代的杂烷基； R2 是羟基、氨基、烷氧基、烷氧基； n 是 1、2 或 3； R3 是芳基、杂芳基、环烷基、氨基低级烷基、芳基； R4 是氢或低级烷基；或 R3 和 R4 连接形成具有下式的环： R6是氢或低级烷基；p是1、2或3；W是键、-CH2-或C=O；Z是键、- -或- -；及其药学上可接受的盐。
• Amide derivatives
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0084941A1

  公开（公告）日：1983-08-03

  Amide derivatives of the formula wherein either R1 is aryl or heterocyclic and A is a direct link, or R1 is aryl or heterocyclic, or hydrogen, or halogeno, hydroxy, amino, guanidino, mercapto, carboxy, carbamoyl, or a substituted derivative thereof, and A1 is alkylene, alkenylene, cycloalkylene or cycloalkenylene; wherein X is carbonyl or hydroxymethylene or substituted derivatives thereof; wherein A2 is alkylene, alkenylene or alkylidene; wherein R2 is hydrogen or alkyl which is unsubsituted or which bears an aryl substituent, or R2 has the formula -Q2-R20 as defined below; wherein R3 is hydrogen, alkyl or a carbonyl-containing group; wherein R4 is hydrogen or alkyl which is unsubstituted or which bears a halogeno, hydroxy, amino, guanidino, carboxy, carbamoyl, mercapto, alkoxy, alkylamino, dialkylamino, cyclic amino, alkylthio, alkanoylamino, alkoxycarbonylamino, alkoxycarbonyl, aryl or heterocyclyl substituent; wherein -NR5-CR6R16-Q1-R10 is an amino acid residue, R5, R6 and R16 being defined in claim 1, wherein Q1 and Q2, which may be the same or different, each is carbonyl (-CO-) or methylene (-CH2-); and wherein R10 and R20, which may be the same or different, is hydroxy, amino or a substituted derivative thereof or hydroxyamino or arylthio; or a salt thereof where appropriate; processes for their manufacture and pharmaceutical compositions containing them. The compounds are inhibitors of angiotensin converting enzyme and may be used in the treatment of hypertension.

  式中的酰胺衍生物 其中 R1 为芳基或杂环且 A 为直接连接，或 R1 为芳基或杂环、或氢、或卤素、羟基、氨基、胍基、巯基、羧基、氨基甲酰基或其取代衍生物，且 A1 为亚烷基、亚烯基、环亚烷基或环烯基；其中 X 为羰基或羟甲基或其取代衍生物； 其中 A2 为亚烷基、亚烯基或亚烷基； 其中 R2 为氢或未取代的烷基或带有芳基取代基的烷基，或 R2 具有如下定义的式 -Q2-R20 ； 其中 R3 为氢、烷基或含羰基的基团；其中 R4 是氢或未取代的烷基，或带有卤素、羟基、氨基、胍基、羧基、氨基甲酰基、巯基、烷氧基、烷基氨基、二烷基氨基、环氨基、烷硫基、烷酰氨基、烷氧基羰基氨基、烷氧基羰基、芳基或杂环烷基取代基；其中-NR5-CR6R16-Q1-R10是氨基酸残基，R5、R6和R16在权利要求1中定义，其中Q1和Q2可以相同或不同，各自是羰基(-CO-)或亚甲基(-CH2-)；其中R10和R20可以相同或不同，是羟基、氨基或其取代衍生物或羟基氨基或芳硫基；或其适当的盐；其制造工艺和含有它们的药物组合物。这些化合物是血管紧张素转换酶的抑制剂，可用于治疗高血压。
• US4528282A
  申请人：——

  公开号：US4528282A

  公开（公告）日：1985-07-09