H-Ala-(D)-iso-Glu-(OMe)-Lys-(N^ε-COCF3)-(D)-Ala-(D)-Ala-OMe | 202464-68-4

• 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: H-Ala-(D)-iso-Glu-(OMe)-Lys-(N^ε-COCF3)-(D)-Ala-(D)-Ala-OMe
• 英文别名: H-Ala-D-iso-Glu(OMe)-Lys(Tfa)-D-Ala-D-Ala-OMe；H-Ala-D-gGlu(OMe)-Lys(Tfa)-D-Ala-D-Ala-OMe；methyl (2R)-2-[[(2S)-2-aminopropanoyl]amino]-5-[[(2S)-1-[[(2R)-1-[[(2R)-1-methoxy-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxo-6-[(2,2,2-trifluoroacetyl)amino]hexan-2-yl]amino]-5-oxopentanoate
• CAS: 202464-68-4
• 化学式: C₂₄H₃₉F₃N₆O₉
• 分子量: 612.604
• InChiKey: ZOGSPPHMJALFMN-CQJMVSDSSA-N

物化性质

• 沸点：
  886.0±65.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  42
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  224
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  H-Ala-(D)-iso-Glu-(OMe)-Lys-(N^ε-COCF3)-(D)-Ala-(D)-Ala-OMe 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 、 水 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 UDP-MurNAc-L-Ala-D-Glu-γ-L-Lys-D-Ala-D-Ala
  参考文献：
  名称：

  一种有效的化学酶策略，用于合成野生型和耐万古霉素的细菌细胞壁前体：UDP-N-乙酰基muramyl-肽。

  摘要：

  DOI：

  10.1021/ja011708w
• 作为产物：
  描述：

  N-叔丁氧羰基-D-谷氨酸 1-甲酯 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 92.0h， 生成 H-Ala-(D)-iso-Glu-(OMe)-Lys-(N^ε-COCF3)-(D)-Ala-(D)-Ala-OMe
  参考文献：
  名称：

  Synthesis of a radioiodinated park nucleotide analog: a new tool for antibacterial screen development

  摘要：

  The Park nucleotide is an important biological building block used in the construction of bacterial cell walls. Herein, we describe the synthesis of a radiolabeled Park nucleotide analog, p-iodophenoxyacyl-Ala-(D)-iso-Glu-Lys-(D)-Ala-(D)-Ala-OH-[I-125], using electrophilic destannylation. Anti-Park nucleotide antibody binding assays using a scintillation proximity assay (SPA) system showed good recognition of the radiolabeled surrogate. This methodology could be used for establishing a screen to identify inhibitors of peptidoglycan biosynthesis.

  DOI：

  10.1002/(sici)1099-1344(1998080)41:8<705::aid-jlcr119>3.0.co;2-n

文献信息

• A New Synthetic Approach toward Bacterial Transglycosylase Substrates, Lipid II and Lipid IV
  作者：Hao-Wei Shih、Kuo-Ting Chen、Ting-Jen R Cheng、Chi-Huey Wong、Wei-Chieh Cheng

  DOI：10.1021/ol201806d

  日期：2011.9.2

  A new synthetic approach toward the bacterial transglycosylase substrates, Lipid II (1) and Lipid IV (2), is described. The key disaccharide was synthesized using the concept of relative reactivity value (RRV) and elaborated to Lipid II and Lipid IV by conjugation with the appropriate oligopeptides and pyrophosphate lipids. Interestingly, the results from our HPLC-based functional TGase assay suggested

  描述了一种针对细菌转糖基化酶底物的新合成方法，脂质II（1）和脂质IV（2）。使用相对反应性值（RRV）的概念合成了关键的二糖，并通过与适当的寡肽和焦磷酸酯脂质缀合将其精制为脂质II和脂质IV。有趣的是，我们基于HPLC的功能TGase检测的结果表明，脂质IV对酶的亲和力比脂质II高。
• Synthesis of 4-Fluorinated UDP-MurNAc Pentapeptide as an Inhibitor of Bacterial Growth
  作者：Taichi Ueda、Fei Feng、Reiko Sadamoto、Kenichi Niikura、Kenji Monde、Shin-Ichiro Nishimura

  DOI：10.1021/ol049598w

  日期：2004.5.1

  4-Fluorinated UDP-MurNAc pentapeptide, 2, has been synthesized. In our previous study, UDP-MurNAc pentapeptide analogue 1 was found to be incorporated into the bacterial cell wall through biosynthesis. Compound 2 showed growth-inhibition activity against Gram-positive bacteria when it was added to growth media at 0.01 mg/mL.
• N-Methylimidazolium chloride-catalyzed pyrophosphate formation: Application to the synthesis of Lipid I and NDP-sugar donors
  作者：Hirokazu Tsukamoto、Daniel Kahne

  DOI：10.1016/j.bmcl.2011.04.061

  日期：2011.9

  N-Methylimidazolium chloride is found to catalyze a coupling reaction between monophosphates and activated phosphorous-nitrogen intermediates such as a phosphorimidazolide and phosphoromorpholidate to form biologically important unsymmetrical pyrophosphate diesters. The catalyst is much more active, cheaper, and less explosive than 1H-tetrazole, known as the best catalyst for the pyrophosphate formation over a decade. The mild and neutral reaction conditions are compatible with allylic pyrophosphate formation in Lipid I syntheisis. (31)P NMR experiments suggest that the catalyst acts not only as an acid but also as a nucleophile to form cationic and electrophilic phosphor-N-methylimidazolide intermediates in the pyrophosphate formation. (c) 2011 Elsevier Ltd. All rights reserved.
• An Efficient Chemoenzymatic Strategy for the Synthesis of Wild-Type and Vancomycin-Resistant Bacterial Cell-Wall Precursors:  UDP-<i>N</i>-acetylmuramyl-peptides
  作者：Haitian Liu、Reiko Sadamoto、Pamela S. Sears、Chi-Huey Wong

  DOI：10.1021/ja011708w

  日期：2001.10.1
• Synthesis of a radioiodinated park nucleotide analog: a new tool for antibacterial screen development
  作者：Clark N. Eid、Michael J. Nesler、Mohammad Zia-Ebrahimi、Chuyn-Yeh Ernie Wu、Raymond Yao、Karen Cox、John Richardson

  DOI：10.1002/(sici)1099-1344(1998080)41:8<705::aid-jlcr119>3.0.co;2-n

  日期：1998.8

  The Park nucleotide is an important biological building block used in the construction of bacterial cell walls. Herein, we describe the synthesis of a radiolabeled Park nucleotide analog, p-iodophenoxyacyl-Ala-(D)-iso-Glu-Lys-(D)-Ala-(D)-Ala-OH-[I-125], using electrophilic destannylation. Anti-Park nucleotide antibody binding assays using a scintillation proximity assay (SPA) system showed good recognition of the radiolabeled surrogate. This methodology could be used for establishing a screen to identify inhibitors of peptidoglycan biosynthesis.