(S)-2-Amino-N-hydroxy-N-methyl-propionamide | 146540-05-8

• 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: (S)-2-Amino-N-hydroxy-N-methyl-propionamide
• 英文别名: (2S)-2-amino-N-hydroxy-N-methylpropanamide
• CAS: 146540-05-8
• 化学式: C₄H₁₀N₂O₂
• 分子量: 118.136
• InChiKey: VEGDCVNJCRACLL-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  66.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-Amino-N-hydroxy-N-methyl-propionamide 、 (2,3,4,5,6-Pentachlorophenyl) 3-[2-[[3-[4-(4-nitro-2,1,3-benzoxadiazol-7-yl)piperazin-1-yl]-3-oxopropoxy]methyl]-3-[3-oxo-3-(2,3,4,5,6-pentachlorophenoxy)propoxy]-2-[[3-oxo-3-(2,3,4,5,6-pentachlorophenoxy)propoxy]methyl]propoxy]propanoate 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 以48%的产率得到(2S)-2-[3-[2,2-bis[[3-[[(2S)-1-[hydroxy(methyl)amino]-1-oxopropan-2-yl]amino]-3-oxopropoxy]methyl]-3-[3-[4-(4-nitro-2,1,3-benzoxadiazol-7-yl)piperazin-1-yl]-3-oxopropoxy]propoxy]propanoylamino]-N-hydroxy-N-methylpropanamide
  参考文献：
  名称：

  Modular Fluorescent-Labeled Siderophore Analogues

  摘要：

  Biomimetic analogues 1 of the microbial siderophore (iron carrier) ferrichrome were labeled via piperazine with various fluorescent markers at a site not interfering with iron binding or receptor recognition (compounds 10-12). These iron carriers were built from a tetrahedral carbon symmetrically extended with three strands, each containing an amino acid (G = glycyl, A = alanyl, L = leucyl and P = phenylalanyl) and terminated by a hydroxamic acid, which together define an octahedral iron-binding domain. A fourth exogenous strand provided the site for connecting various fluorescent markers via a short bifunctional linker. Iron(III) titrations, along with fluorescence spectroscopy, generated quenching of fluorescence emission of some of the probes used. The quenching process fits the Perrin model which reinforces the intramolecular quenching process, postulated previously.(1) All tested compounds, regardless of their probe size, polarity, or the linker binding them to the siderophore analogue, promote growth of Pseudomonas putida with the same efficacy as the nonlabeled analogues 1, with the added benefit of signaling microbial activity by fluorescence emission. All G derivatives of compounds 10-12 were found to parallel the behavior of natural ferrichrome, whereas A derivatives mediated only a modest iron(III) uptake by P. putida. Incubation of various Pseudomonas strains with iron(III)-loaded G derivatives resulted in the build-up of the labels' fluorescence in the culture medium to a much larger extent than from the corresponding A derivatives. The fluorescence buildup corresponds to iron utilization by the cells and the release of the fluorescent labeled desferrisiderophore from the cell to the media. The fact that the microbial activity of these compounds is not altered by attachment of various fluorescent markers via a bifunctional linker proposes their application as diagnostic tools for detecting and identifying pathogenic microorganisms.

  DOI：

  10.1021/jm970581b
• 作为产物：
  描述：

  [(S)-1-(Hydroxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 (S)-2-Amino-N-hydroxy-N-methyl-propionamide
  参考文献：
  名称：

  Modular Fluorescent-Labeled Siderophore Analogues

  摘要：

  Biomimetic analogues 1 of the microbial siderophore (iron carrier) ferrichrome were labeled via piperazine with various fluorescent markers at a site not interfering with iron binding or receptor recognition (compounds 10-12). These iron carriers were built from a tetrahedral carbon symmetrically extended with three strands, each containing an amino acid (G = glycyl, A = alanyl, L = leucyl and P = phenylalanyl) and terminated by a hydroxamic acid, which together define an octahedral iron-binding domain. A fourth exogenous strand provided the site for connecting various fluorescent markers via a short bifunctional linker. Iron(III) titrations, along with fluorescence spectroscopy, generated quenching of fluorescence emission of some of the probes used. The quenching process fits the Perrin model which reinforces the intramolecular quenching process, postulated previously.(1) All tested compounds, regardless of their probe size, polarity, or the linker binding them to the siderophore analogue, promote growth of Pseudomonas putida with the same efficacy as the nonlabeled analogues 1, with the added benefit of signaling microbial activity by fluorescence emission. All G derivatives of compounds 10-12 were found to parallel the behavior of natural ferrichrome, whereas A derivatives mediated only a modest iron(III) uptake by P. putida. Incubation of various Pseudomonas strains with iron(III)-loaded G derivatives resulted in the build-up of the labels' fluorescence in the culture medium to a much larger extent than from the corresponding A derivatives. The fluorescence buildup corresponds to iron utilization by the cells and the release of the fluorescent labeled desferrisiderophore from the cell to the media. The fact that the microbial activity of these compounds is not altered by attachment of various fluorescent markers via a bifunctional linker proposes their application as diagnostic tools for detecting and identifying pathogenic microorganisms.

  DOI：

  10.1021/jm970581b

文献信息

• Fluorescently-Labeled Ferrichrome Analogs as Probes for Receptor-Mediated, Microbial Iron Uptake
  作者：Haim Weizman、Orly Ardon、Brenda Mester、Jacqueline Libman、Oren Dwir、Yitzhak Hadar、Yona Chen、Abraham Shanzer

  DOI：10.1021/ja9610646

  日期：1996.1.1

  Biomimetic analogs 1 of the microbial siderophore (iron carrier) ferrichrome were labeled with a fluorescent marker at a site which does not interfere with iron binding or receptor recognition to provide iron(III) carriers 5 and 10 (Figure 1). These carriers were built from a tetrahedral carbon as an anchor which was symmetrically extended by three converging iron-binding chains and a single, exogenous

  微生物铁载体（铁载体）铁色素的仿生类似物 1 在不干扰铁结合或受体识别的位点用荧光标记物标记，以提供铁 (III) 载体 5 和 10（图 1）。这些载体由作为锚的四面体碳构建而成，该锚由三个会聚的铁结合链和一个单一的外源性蒽基残基对称延伸。载体 5 的氨基酸性质不同（G = 甘氨酰，A = 丙氨酰和 L = 亮氨酰）将锚与铁结合异羟肟酸基团连接起来，而丙氨酰衍生物 10A 与 5A 的不同之处在于蒽基标记和锚。通过 1 H NMR 检查这些结合剂证实它们的构象与未标记的母体化合物的构象相似。
• Modular Fluorescent-Labeled Siderophore Analogues
  作者：Raphael Nudelman、Orly Ardon、Yitzhak Hadar、Yona Chen、Jacqueline Libman、Abraham Shanzer

  DOI：10.1021/jm970581b

  日期：1998.5.1

  Biomimetic analogues 1 of the microbial siderophore (iron carrier) ferrichrome were labeled via piperazine with various fluorescent markers at a site not interfering with iron binding or receptor recognition (compounds 10-12). These iron carriers were built from a tetrahedral carbon symmetrically extended with three strands, each containing an amino acid (G = glycyl, A = alanyl, L = leucyl and P = phenylalanyl) and terminated by a hydroxamic acid, which together define an octahedral iron-binding domain. A fourth exogenous strand provided the site for connecting various fluorescent markers via a short bifunctional linker. Iron(III) titrations, along with fluorescence spectroscopy, generated quenching of fluorescence emission of some of the probes used. The quenching process fits the Perrin model which reinforces the intramolecular quenching process, postulated previously.(1) All tested compounds, regardless of their probe size, polarity, or the linker binding them to the siderophore analogue, promote growth of Pseudomonas putida with the same efficacy as the nonlabeled analogues 1, with the added benefit of signaling microbial activity by fluorescence emission. All G derivatives of compounds 10-12 were found to parallel the behavior of natural ferrichrome, whereas A derivatives mediated only a modest iron(III) uptake by P. putida. Incubation of various Pseudomonas strains with iron(III)-loaded G derivatives resulted in the build-up of the labels' fluorescence in the culture medium to a much larger extent than from the corresponding A derivatives. The fluorescence buildup corresponds to iron utilization by the cells and the release of the fluorescent labeled desferrisiderophore from the cell to the media. The fact that the microbial activity of these compounds is not altered by attachment of various fluorescent markers via a bifunctional linker proposes their application as diagnostic tools for detecting and identifying pathogenic microorganisms.