(2R,3R)-2-氨基-3-甲氧基丁酸 | 104195-79-1

• 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
• 中文名称: (2R,3R)-2-氨基-3-甲氧基丁酸
• 英文名称: O-methyl-D-allothreonine
• 英文别名: O-methyl-D-allothreonine；O-Methyl-D-allothreonin；D-O-methylallothreonine；O-methyl-L-threonine；L-(2R:3R)-O-Methylthreonin；DL-O-Methyl-allothreonin；(2R,3R)-2-amino-3-methoxybutanoic acid
• CAS: 104195-79-1
• 化学式: C₅H₁₁NO₃
• 分子量: 133.147
• InChiKey: FYCWLJLGIAUCCL-QWWZWVQMSA-N

物化性质

• 沸点：
  248.0±30.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-氨基-3-甲氧基丁酸 、 氯甲酸甲酯 在 sodium hydroxide 、 盐酸 、 水 作用下， 以 水 为溶剂， 反应 12.0h， 生成 N-(Methoxycarbonyl)-O-methyl-D-allothreonine
  参考文献：
  名称：

  [EN] HEPATITIS C VIRUS INHIBITORS
  [FR] INHIBITEURS DU VIRUS DE L'HÉPATITE C

  摘要：

  本公开涉及（4-4'-二咪唑基）联苯类化合物及用于治疗丙型肝炎病毒（HCV）感染的方法。还公开了含有这些化合物的药物组合物以及在治疗HCV感染中使用这些化合物的方法。

  公开号：

  WO2009102318A1
• 作为产物：
  描述：

  methyl (2R,3R)-2-(tert-butoxycarbonylamino)-3-methoxybutanoate 在 盐酸 作用下， 以 水 为溶剂， 反应 16.0h， 生成 (2R,3R)-2-氨基-3-甲氧基丁酸
  参考文献：
  名称：

  Minutissamides E–L, antiproliferative cyclic lipodecapeptides from the cultured freshwater cyanobacterium cf. Anabaena sp.

  摘要：

  The extract of UIC 10035, a strain obtained from a sample collected near the town of Homestead, South Florida, showed antiproliferative activity against MDA-MB-435 cells. Bioassay-guided fractionation led to the isolation of a series of cyclic lipodecapeptides, named minutissamides E-L (1-8). The planar structures were determined by analysis of HRESIMS, tandem MS, and 1D and 2D NMR data, and the stereo-configurations were assigned by LC-MS analysis of the Marfey's derivatives after acid hydrolysis. Minutissamides E-L (1-8) exhibited antiproliferative activity against MDA-MB-435 cells with IC50 values ranging between 1 and 10 mu M. The structures of minutissamides E-L (1-8) were closely related with those of the previously reported lipopeptides, puwainaphycins A-E and minutissamides A-D, characterized by the presence of a lipophilic beta-amino acid and three non-standard amino acids NMeAsn, OMeThr and Dhb (alpha,beta-dehydro-alpha-aminobutyric acid). The strain UIC 10035 was designated as cf. Anabaena sp. on the basis of morphological and 16S rRNA gene sequence analyses. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.017

文献信息

• A search for peptide ligase: cosolvent-mediated conversion of proteases to esterases for irreversible synthesis of peptides
  作者：Carlos F. Barbas、Jose R. Matos、J. Blair. West、Chi Huey. Wong

  DOI：10.1021/ja00223a042

  日期：1988.7

  Further, the reactions can be carried out in a mixture of organic solvent and water, devoid of the problem of low solubility of protected peptides in the organic solvents employed in chemical synthesis. With these advantages, however, come the disadvantages that the amidase activity of proteases causes a secondary hydrolysis of the growing peptides and that the substrates of proteases are generally limited

  丝氨酸和半胱氨酸蛋白酶（胰蛋白酶、胰凝乳蛋白酶、木瓜蛋白酶、枯草杆菌蛋白酶）在一定浓度的水溶性有机溶剂中不表现出酰胺酶活性。然而，酯酶活性仍然显着。这些修饰的酶可以在动力学控制方法（氨解）中用作肽连接酶，用于肽的逐步合成和片段偶联，其产物没有二次水解。展示了在这种条件下合成含有 D 和 L-氨基酸以及含有 0-甲基-D-别苏氨酸和α-氨基己二酸的青霉素前体的肽。Z-Phe-Leu-NH 在无水 DMF 和含水 DMF（50% 水，v/v）中的酶促合成的比较研究表明，在含水 DMF 中的速率要快 10000 倍以上。胰凝乳蛋白酶，枯草杆菌蛋白酶和灰色链霉菌蛋白酶对无水 DMF 中的 Z-Phe-OMe + Leu-NH2 无活性。蛋白酶在肽合成中作为催化剂的利用始于本世纪初 2，并且仍然是一个活跃的研究领域。~ 部分流程已经商业化；尤其重要的是生产阿斯巴甜 4 和人胰岛素 5 酶促肽合成的优
• Studies on Diastereoisomeric α-Amino Acids and Corresponding α-Hydroxy Acids. VII. Influence of β-Configuration on Enzymic Susceptibility
  作者：Milton Winitz、Leah Bloch-Frankenthal、Nobuo Izumiya、Sanford M. Birnbaum、Carl G. Baker、Jesse P. Greenstein

  DOI：10.1021/ja01592a022

  日期：1956.6
• Perthamides C and D, two new potent anti-inflammatory cyclopeptides from a Solomon Lithistid sponge Theonella swinhoei
  作者：Carmen Festa、Simona De Marino、Valentina Sepe、Maria Chiara Monti、Paolo Luciano、Maria Valeria D'Auria、Cecile Débitus、Mariarosaria Bucci、Valentina Vellecco、Angela Zampella

  DOI：10.1016/j.tet.2009.10.026

  日期：2009.12

  Two new metabolites, perthamides C and D, have been isolated from the marine sponge Theonella swinhoei. Their structures were determined by interpretation of NMR and ESIMS data. All compounds exhibited in vivo potent anti-inflammatory activity. Biological activity and structural elucidation are reported. (C) 2009 Elsevier Ltd. All rights reserved.
• [EN] HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2009102318A1

  公开（公告）日：2009-08-20

  The present disclosure relates to (4-4' -diimidazolyl) biphenyls compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.

  本公开涉及（4-4'-二咪唑基）联苯类化合物及用于治疗丙型肝炎病毒（HCV）感染的方法。还公开了含有这些化合物的药物组合物以及在治疗HCV感染中使用这些化合物的方法。
• Minutissamides E–L, antiproliferative cyclic lipodecapeptides from the cultured freshwater cyanobacterium cf. Anabaena sp.
  作者：Hahk-Soo Kang、Megan Sturdy、Aleksej Krunic、Hyunjung Kim、Qi Shen、Steven M. Swanson、Jimmy Orjala

  DOI：10.1016/j.bmc.2012.08.017

  日期：2012.10

  The extract of UIC 10035, a strain obtained from a sample collected near the town of Homestead, South Florida, showed antiproliferative activity against MDA-MB-435 cells. Bioassay-guided fractionation led to the isolation of a series of cyclic lipodecapeptides, named minutissamides E-L (1-8). The planar structures were determined by analysis of HRESIMS, tandem MS, and 1D and 2D NMR data, and the stereo-configurations were assigned by LC-MS analysis of the Marfey's derivatives after acid hydrolysis. Minutissamides E-L (1-8) exhibited antiproliferative activity against MDA-MB-435 cells with IC50 values ranging between 1 and 10 mu M. The structures of minutissamides E-L (1-8) were closely related with those of the previously reported lipopeptides, puwainaphycins A-E and minutissamides A-D, characterized by the presence of a lipophilic beta-amino acid and three non-standard amino acids NMeAsn, OMeThr and Dhb (alpha,beta-dehydro-alpha-aminobutyric acid). The strain UIC 10035 was designated as cf. Anabaena sp. on the basis of morphological and 16S rRNA gene sequence analyses. (C) 2012 Elsevier Ltd. All rights reserved.