AcMet-Pro

• 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: AcMet-Pro
• 英文别名: N-acetyl-D-methionyl-L-proline；Ac-Met-Pro-OH；(2S)-1-[(2S)-2-acetamido-4-methylsulfanylbutanoyl]pyrrolidine-2-carboxylic acid
• 化学式: C₁₂H₂₀N₂O₄S
• 分子量: 288.368
• InChiKey: ZYFRCWPUJYULPG-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  AcMet-Pro 在 dinuclear palladium(II) hexaazacyclooctadecane 高氯酸 、 3-(trimethylsilyl)-1-propanesulfonic acid,sodium salt 作用下， 以 重水 为溶剂， 生成 N-乙酰-L-蛋氨酸 、 L-脯氨酸
  参考文献：
  名称：

  两个金属中心在双核钯（II）六氮杂环十八烷配合物催化的蛋氨酸肽催化水解中的协同作用

  摘要：

  通过[Pd 2（[18] aneN 6）Cl 2 ]（ClO 4）2 （其中[18] aneN 6为1,4,7,10,13,16-六氮杂环十八烷）与AgBF 4反应获得的物质由...决定电喷雾电离质谱 （电喷雾质谱）是三种主要类型的双核Pd（II）配合物的平衡混合物阳离子，[Pd 2（μ-O）（[18] aneN 6）] 2 +，[Pd 2（μ-OH）（[18] aneN 6）] 3+和[Pd 2（H 2 O）（OH） （[18] aneN 6）] 3+，在水溶液中。羟基基团桥接的[Pd 2（μ-OH）（[18] aneN 6）] 3+是占主导地位的物种，其晶体结构已获得。[Pd 2（μ-OH）（[18] aneN 6）]（ClO 4）3的晶体结构表明，双核络合物中的每个Pd（II）离子四配位为三个氮原子以及一个变形的方形构型的羟基基团桥。两个Pd（II）离子彼此相距3.09Å。双核钯（II）配合物阳离子[Pd

  DOI：

  10.1039/b500210a

文献信息

• Downstream reaction of cisplatin with methionine-containing peptides: pH-dependent competition between hydrolytic cleavage and macrochelation
  作者：Oliver Hohage、Sven Manka、William S. Sheldrick

  DOI：10.1016/j.ica.2008.01.011

  日期：2009.2

  The pH-and time-dependent reactions of the antitumor drug cisplatin, cis-[PtCl2(NH3)(2)], with the methionine-containing peptides Ac-Met-Gly-OH, Ac-Met-Pro-OH, Ac-Met-Pro-Gly-Gly-OH and Ac-Gly-Met-Pro-Gly-Gly-OH (Gly = glycyl, Met = D-methionyl, Pro = L-prolyl) at 313 K have been investigated by high performance liquid chromatography, mass spectrometry and nuclear magnetic resonance. As a result of the strong trans influence of the methionyl S-M atom, initial Pt-S-M binding at pH > 5 is followed by a rapid formation of tridentate machrochelates for the N-acetylated peptides. The site trans to S-M is occupied by a carboxylate O atom in the case of the kappa S-3(M),N-M,O-G/P macrochelates of the dipeptides and by the C-terminal glycylamide N-G2 atom for the kappa S-3(M),O-M,N-G2 macrochelate of Ac-Met-Pro-Gly-Gly-OH. Cisplatin simultaneously mediates the rapid hydrolytic cleavage of the Met-X (X = Gly, Pro) amide bond for both dipeptides over the whole range 2.8 <= pH <= 10.0. The released amino acids X react with the resulting kappa S-2(M),N-M chelate of N-acetylmethionine to afford mixed kappa S-M:kappa N-2(x),O-x complexes of the type cis-[Pt(NH3)(Ac-Met-OH-kappa S)(H-X-O-kappa N-2(x),O-x)](+) as final products at pH < 5 for X = Gly and pH < 8 for X = Pro. In contrast to the dipeptides, hydrolytic cleavage of the Met-Pro amide bond in Ac-Met-Pro-Gly-Gly-OH at pH > 5 is significantly inhibited by the presence of high concentrations of the macrochelate [Pt(NH3)(Ac-Met-Pro-Gly-Gly)-kappa S-3(M),O-M,N-G2](+). Downstream hydrolysis of the Met-Gly amide bond is competitive with upstream Ac-Gly cleavage for Ac-Gly-Met-Pro-Gly-Gly-OH at pH < 4.5. (C) 2008 Elsevier B. V. All rights reserved.
• Synergic effect of two metal centers in catalytic hydrolysis of methionine-containing peptides promoted by dinuclear palladium(ii) hexaazacyclooctadecane complex
  作者：Gaosheng Yang、Ren Miao、Yizhi Li、Jing Hong、Chuenmei Zhao、Zijian Guo、Longgen Zhu

  DOI：10.1039/b500210a

  日期：——

  The two Pd(II) ions are 3.09 Å apart from each other. The dinuclear Pd(II) complex cations [Pd2(μ-OH)([18]aneN6)]3+ and [Pd2(H2O)(OH)([18]aneN6)]3+ can efficiently catalyze hydrolysis of the amide bond involving the carbonyl group of methionine in methionine-containing peptides with turnover number of larger than 20. In these hydrolytic reactions, the two Pd(II) ions are synergic; one Pd(II) ion anchors

  通过[Pd 2（[18] aneN 6）Cl 2 ]（ClO 4）2 （其中[18] aneN 6为1,4,7,10,13,16-六氮杂环十八烷）与AgBF 4反应获得的物质由...决定电喷雾电离质谱 （电喷雾质谱）是三种主要类型的双核Pd（II）配合物的平衡混合物阳离子，[Pd 2（μ-O）（[18] aneN 6）] 2 +，[Pd 2（μ-OH）（[18] aneN 6）] 3+和[Pd 2（H 2 O）（OH） （[18] aneN 6）] 3+，在水溶液中。羟基基团桥接的[Pd 2（μ-OH）（[18] aneN 6）] 3+是占主导地位的物种，其晶体结构已获得。[Pd 2（μ-OH）（[18] aneN 6）]（ClO 4）3的晶体结构表明，双核络合物中的每个Pd（II）离子四配位为三个氮原子以及一个变形的方形构型的羟基基团桥。两个Pd（II）离子彼此相距3.09Å。双核钯（II）配合物阳离子[Pd