N-(tert-butyloxycarbonyl)-L-<4,4-2H2>homoserine tert-butyl ester | 114059-77-7

• 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: N-(tert-butyloxycarbonyl)-L-<4,4-2H2>homoserine tert-butyl ester
• 英文别名: N-Boc-(4,4-(2)H2)homoserine-α-OtBu；tert-butyl (2S)-4,4-dideuterio-4-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 114059-77-7
• 化学式: C₁₃H₂₅NO₅
• 分子量: 277.329
• InChiKey: WFSWHDJTFHDJFE-GZIXFAMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(tert-butyloxycarbonyl)-L-<4,4-2H2>homoserine tert-butyl ester 在 Collins oxidation agent 作用下， 以70%的产率得到1-tert-butyl L-2-<(tert-butyloxycarbonyl)amino>-<4-2H>-4-oxobutanoate
  参考文献：
  名称：

  Synthesis of stereospecific deuterium-labeled homoserines and homoserine lactones

  摘要：

  DOI：

  10.1021/jo00244a012
• 作为产物：
  描述：

  Boc-L-天冬氨酸 4-甲酯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 硼氘化钠 、 重水 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 19.75h， 生成 N-(tert-butyloxycarbonyl)-L-<4,4-2H2>homoserine tert-butyl ester
  参考文献：
  名称：

  Synthesis of stereospecific deuterium-labeled homoserines and homoserine lactones

  摘要：

  DOI：

  10.1021/jo00244a012

文献信息

• Detection and Quantitation of Bacterial Acylhomoserine Lactone Quorum Sensing Molecules via Liquid Chromatography–Isotope Dilution Tandem Mass Spectrometry
  作者：Amanda L. May、Mary E. Eisenhauer、Kristen S. Coulston、Shawn R. Campagna

  DOI：10.1021/ac202636d

  日期：2012.2.7

  A range of acylhomoserine lactones (AHLs) are used as intraspecies quorum sensing signals by Gram-negative bacteria, and the detection and quantitation of these molecules is of interest. This manuscript reports a liquid chromatographic–isotope dilution tandem mass spectrometric method for the quantitation of these molecules. A divergent solid-phase synthesis of stable-isotope-labeled AHLs suitable for use as an internal standard is reported. This route relies on the biomimetic conversion of a dideuterated methionine equivalent, N-Fmoc-(4,4-2H2)methionine, to the desired labeled AHL, and a representative series of eight of these molecules was produced in >95% purity and yields up to ∼50%. The representative AHL internal standards were then used to develop an optimized liquid chromatography—tandem mass spectrometric (LC–MS/MS) separation and detection protocol for these molecules, which relies on a high-efficiency C18 core–shell column to minimize the time necessary for separation. The addition of internal standards at different steps during sampling was also found to affect the analysis for hydrophobic AHLs with addition prior to cell removal giving the most accurate results. Taken together, the use of the internal standards and separation method reported herein provides a rapid and quantitative method for the study of AHL production in bacteria.

  一系列酰基高丝氨酸内酯（AHLs）作为革兰氏阴性菌的种内群体感应信号分子，对这些分子的检测和定量研究具有重要意义。本文报道了一种液相色谱-同位素稀释串联质谱法用于这些分子的定量分析。文中还报道了一种固相合成适合作内标物的稳定同位素标记AHLs的方法。该合成路线依赖于生物模拟转化二氘代甲硫氨酸类似物N-Fmoc-(4,4-2H2)甲硫氨酸至所需标记AHL的过程。我们成功制备了八个代表性分子，纯度>95%，产率高达约50%。然后，使用这些代表性AHL内部标准物，开发了一套优化的液相色谱-串联质谱（LC-MS/MS）分离与检测方案，该方案依赖于高效C18核壳柱以最小化分离所需时间。在采样过程中不同步骤添加内标物对疏水性AHL分析的影响也得到了研究，发现在细胞去除前添加内标物可获得最准确的结果。综上所述，本文报道的内标物和分离方法提供了一种快速且定量的方法用于研究细菌中AHL的产生。
• Hyperpolarized [5- ¹³ C,4,4- ² H ₂ ,5- ¹⁵ N]-L-glutamine provides a means of annotating in vivo metabolic utilization of glutamine
  作者：Roozbeh Eskandari、Nathaniel Kim、Arsen Mamakhanyan、Michelle Saoi、Guannan Zhang、Marjan Berishaj、Kristin L. Granlund、Alex J. Poot、Justin Cross、Craig B. Thompson、Kayvan R. Keshari

  DOI：10.1073/pnas.2120595119

  日期：2022.5.10

  Glutamine is the most abundant amino acid in human plasma, although it is challenging to determine glutamine’s metabolic fate noninvasively. In this work, we utilize established chemical methods to develop a platform for imaging glutamine metabolism using hyperpolarized magnetic resonance imaging. Using this strategy, we are able to spatially measure glutaminolysis in vivo as well as develop a biomarker for the inhibition of glutaminase. Combining this biomarker with isotope tracing metabolomics connects this inhibition to reduced glutamine contribution to the tricarboxylic acid cycle. This provides an approach for future imaging of glutamine metabolism in humans.

  谷氨酰胺是人体血浆中最丰富的氨基酸，但非侵入性地确定谷氨酰胺的代谢命运具有挑战性。在这项工作中，我们利用已建立的化学方法开发了一种使用超极化磁共振成像来成像谷氨酰胺代谢的平台。利用这种策略，我们能够在体内空间地测量谷氨酰胺的溶解以及开发一种抑制谷氨酰胺酶的生物标志物。将这种生物标志物与同位素示踪代谢组学相结合，将这种抑制与谷氨酰胺对三羧酸循环的贡献减少相联系。这为将来在人类中成像谷氨酰胺代谢提供了一种方法。

• Mechanism of <i>S</i>-Adenosyl-<scp>l</scp>-methionine <i>C</i>-Methylation by Cobalamin-dependent Radical <i>S</i>-Adenosyl-<scp>l</scp>-methionine Methylase in 1-Amino-2-methylcyclopropanecarboxylic Acid Biosynthesis
  作者：Fumitaka Kudo、Atsushi Minato、Shusuke Sato、Nayuta Nagano、Chitose Maruyama、Yoshimitsu Hamano、Junko Hashimoto、Ikuko Kozone、Kazuo Shin-ya、Tadashi Eguchi

  DOI：10.1021/acs.orglett.2c03555

  日期：2022.12.16

  C-methylation of SAM in the biosynthesis of 1-amino-2-methylcyclopropanecarboxylic acid. Here, we determined that the methylation product is (4″R)-4″-methyl-SAM. Furthermore, we found that the 5′-deoxyadenosyl radical generated by Orf29 abstracts the pro-R hydrogen atom from the C-4″ position of SAM to generate the radical intermediate, which reacts with methylcobalamin to give (4″R)-4″-methyl-SAM

  自由基S-腺苷-l-甲硫氨酸 (SAM) 甲基化酶 Orf29在 1-氨基-2-甲基环丙烷甲酸的生物合成中催化SAM 的C-甲基化。在这里，我们确定甲基化产物是(4″ R )-4″-甲基-SAM。此外，我们发现Orf29产生的5′-脱氧腺苷自由基从SAM的C-4”位上夺取pro-R氢原子，生成自由基中间体，该自由基中间体与甲钴胺反应生成(4” R )-4” -甲基-SAM。因此，证实Orf29催化的C-甲基化在构型保留的情况下进行。
• RAMALINGAM, KONDAREDDIAR;WOODARD, RONALD W., J. ORG. CHEM., 53,(1988) N 9, 1900-1903
  作者：RAMALINGAM, KONDAREDDIAR、WOODARD, RONALD W.

  DOI：——

  日期：——
• Synthesis of stereospecific deuterium-labeled homoserines and homoserine lactones
  作者：Kondareddiar Ramalingam、Ronald W. Woodard

  DOI：10.1021/jo00244a012

  日期：1988.4