NH2-Met-Asp-Trp-Asn-Met-His-Ala-Ala-CONH2

• 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: NH2-Met-Asp-Trp-Asn-Met-His-Ala-Ala-CONH2
• 英文别名: H-Met-Asp-Trp-Asn-Met-His-Ala-Ala-NH2；H-MDWNMHAA-NH2；(3S)-4-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-[[(2S)-2-amino-4-methylsulfanylbutanoyl]amino]-4-oxobutanoic acid
• 化学式: C₄₁H₅₉N₁₃O₁₁S₂
• 分子量: 974.132
• InChiKey: ZIBAVGLGBXYKJO-CSGCNXRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  67
• 可旋转键数：
  29
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  448
• 氢给体数：
  13
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  方酸二乙酯 、 NH2-Met-Asp-Trp-Asn-Met-His-Ala-Ala-CONH2 在 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以63%的产率得到
  参考文献：
  名称：

  糖和糖模拟肽作为实验疫苗的蛋白质结合物的合成和免疫化学表征。

  摘要：

  分别被鉴定为A型链球菌和弗氏志贺氏菌的细胞表面多糖的模拟物的肽DRPVPY和MDWNMHAA被用于这项研究中，以开发针对这两种细菌的​​实验疫苗。两种寡肽均采用Fmoc固相策略合成，并通过氨基端连接至双功能连接基二乙基方形。然后将这些加合物与牛血清白蛋白（BSA）和破伤风类毒素（TT）这两种载体蛋白缀合，以生成肽缀合物疫苗。DRPVPY和MDWNMHAA在TT上的平均掺入水平分别为65％和75％，而BSA上两种肽半抗原的掺入平均水平为100％。一种抗弗氏链球菌Y的多糖缀合物，其包含约10个四糖重复单元，还基于在还原端用1，3-二氨基丙烷进行还原胺化，然后将胺化的多糖偶合至二乙基二乙基酯，然后将加合物偶合至TT，制备了氨基甲酸酯。平均掺入了73％的多糖半抗原。已显示糖缀合物和寡肽缀合物有效结合针对细胞表面多糖的各个单克隆抗体。

  DOI：

  10.1016/j.bmc.2004.03.075
• 作为产物：
  描述：

  Fmoc-L-丙氨酸 、 Fmoc-L-色氨酸 、 Fmoc-L-蛋氨酸 、 Fmoc-L-天冬酰胺 、 alkaline earth salt of/the/ methylsulfuric acid 以48%的产率得到NH2-Met-Asp-Trp-Asn-Met-His-Ala-Ala-CONH2
  参考文献：
  名称：

  Rational design and synthesis of peptide ligands for an anti-Carbohydrate antibody and Their immunochemical characterization

  摘要：

  Molecular mimics of carbohydrates present an alternative source of compounds to target pathways involving protein carbohydrate interactions. Certain peptides act as molecular mimics of carbohydrates in binding to anti-carbohydrate antibodies. A series of potential peptide ligands for the anti-carbohydrate antibody SYA/J6, directed against Shigella flexneri Y, was designed by molecular modeling based on a crystal structure of the antibody complex with a carbohydrate-mimetic peptide. These octapeptides were synthesized using solid-phase peptide synthesis, and their recognition by the antibody was investigated. The results shed light on the nature of peptide-carbohydrate mimicry. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00449-2

文献信息

• Synthesis and immunochemical characterization of protein conjugates of carbohydrate and carbohydrate-mimetic peptides as experimental vaccines
  作者：Rehana B Hossany、Margaret A Johnson、Adewale A Eniade、B.Mario Pinto

  DOI：10.1016/j.bmc.2004.03.075

  日期：2004.7

  study to develop experimental vaccines directed against these two bacteria. Both oligopeptides were synthesized employing the Fmoc solid-phase strategy and linked via the amino end to a bifunctional linker, diethylsquarate. These adducts were then conjugated to the two carrier proteins, bovine serum albumin (BSA) and tetanus toxoid (TT) to yield the peptide conjugate vaccines. The average level of incorporation

  分别被鉴定为A型链球菌和弗氏志贺氏菌的细胞表面多糖的模拟物的肽DRPVPY和MDWNMHAA被用于这项研究中，以开发针对这两种细菌的​​实验疫苗。两种寡肽均采用Fmoc固相策略合成，并通过氨基端连接至双功能连接基二乙基方形。然后将这些加合物与牛血清白蛋白（BSA）和破伤风类毒素（TT）这两种载体蛋白缀合，以生成肽缀合物疫苗。DRPVPY和MDWNMHAA在TT上的平均掺入水平分别为65％和75％，而BSA上两种肽半抗原的掺入平均水平为100％。一种抗弗氏链球菌Y的多糖缀合物，其包含约10个四糖重复单元，还基于在还原端用1，3-二氨基丙烷进行还原胺化，然后将胺化的多糖偶合至二乙基二乙基酯，然后将加合物偶合至TT，制备了氨基甲酸酯。平均掺入了73％的多糖半抗原。已显示糖缀合物和寡肽缀合物有效结合针对细胞表面多糖的各个单克隆抗体。
• Rational design and synthesis of peptide ligands for an anti-Carbohydrate antibody and Their immunochemical characterization
  作者：Margaret A Johnson、Adewale A Eniade、B.Mario Pinto

  DOI：10.1016/s0968-0896(02)00449-2

  日期：2003.3

  Molecular mimics of carbohydrates present an alternative source of compounds to target pathways involving protein carbohydrate interactions. Certain peptides act as molecular mimics of carbohydrates in binding to anti-carbohydrate antibodies. A series of potential peptide ligands for the anti-carbohydrate antibody SYA/J6, directed against Shigella flexneri Y, was designed by molecular modeling based on a crystal structure of the antibody complex with a carbohydrate-mimetic peptide. These octapeptides were synthesized using solid-phase peptide synthesis, and their recognition by the antibody was investigated. The results shed light on the nature of peptide-carbohydrate mimicry. (C) 2002 Elsevier Science Ltd. All rights reserved.