desulphosinigrin | 5115-81-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: desulphosinigrin
• 英文别名: desulfosinigrin；1-S-(N-hydroxybut-3-enimidoyl)-1-thio-beta-D-glucopyranose；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] N-hydroxybut-3-enimidothioate
• CAS: 5115-81-1
• 化学式: C₁₀H₁₇NO₆S
• 分子量: 279.314
• InChiKey: NMXWTQFCMCVSFH-HOQQJHGQSA-N

物化性质

• 沸点：
  548.3±60.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  148
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  desulphosinigrin 在 sulfotransferase AtSOT₁₈ from plant 、 C₁₀H₁₁FN₅O₁₃P₂S^(3-) 作用下， 生成 黑介子苷
  参考文献：
  名称：

  用于连续磺基转移酶活性监测和通过 19F NMR 光谱筛选抑制剂的氟化磷酸腺苷 5'-磷酸硫酸盐类似物

  摘要：

  磺基转移酶 (ST) 是普遍存在的酶，它们参与大量涉及硫酰基 (SO 3 ) 转移的生物过程。3'-磷酸腺苷 5'-磷酸硫酸盐 (PAPS) 是通用的 ST 辅因子，是细胞中的“活性硫酸盐”来源。在这里，我们报告了在腺嘌呤的 C2 或 C8 位置带有氟或三氟甲基取代基的三种氟化 PAPS 类似物的合成，以及它们作为替代辅因子的评估，使 ST 活性能够通过 fluorine-19 核磁进行量化和实时监测。共振( 19 F NMR)光谱。使用植物 AtSOT18 和人类 SULT1A3 作为两种模型酶，我们揭示了氟化 PAPS 类似物在酶识别和工作方面显示出互补特性。19 F NMR pH 范围，是研究 ST 的有吸引力的多功能工具。最后，我们开发了一种19 F NMR 检测方法，用于筛选针对 SULT1A3 的潜在抑制剂，从而突出了氟化 PAPS 类似物在发现 ST 相关疾病药物中的可能用途。

  DOI：

  10.1021/acschembio.1c00978
• 作为产物：
  描述：

  sinigrin 在 aryl sulfatase 作用下， 以 aq. acetate buffer 为溶剂， 反应 7.0h， 生成 desulphosinigrin
  参考文献：
  名称：

  Rapid and Efficient Desulfonation Method for the Analysis of Glucosinolates by High-Resolution Liquid Chromatography Coupled with Quadrupole Time-of-Flight Mass Spectrometry

  摘要：

  The goal of our present research was to develop a simple and rapid method for the quantitation of desulfoglucosinolates (desulfoGLS) without using column chromatography. The proposed method involves extraction, concentration, incubation of glucosinolates with a sulfatase enzyme, and HPLC analysis. Identification of desulfoGLS in green kohlrabi was performed by LC-HR-ESI-QTOF-MS in positive-ionization mode. A total of 11 desulfoGLS were identified with neoglucobrassicin (3.32 +/- 0.05 mu mol/g DW) as the predominant indolyl, whereas progoitrin and sinigrin were the major aliphatic desulfoGLS. The levels of the aliphatic desulfoGLS glucoiberin, progoitrin, and glucoerucin at 7 h were found to be 3.6-, 1.9-, and 1.6-fold higher, respectively, than those produced through the conventional method. This technique was successfully applied in the identification of desulfoGLS from cabbage. The developed method has fewer unit operations, has maximum recovery, and is reproducible in the determination of desulfoGLS in a large number of Brassicaceae samples in a short time.

  DOI：

  10.1021/acs.jafc.7b04662

文献信息

• Thioimidate N-Oxides: From Nature to Synthetic Pathways
  作者：Arnaud Tatibouët、Julie Schleiss、Deimante Cerniauskaite、David Gueyrard、Renato Iori、Patrick Rollin

  DOI：10.1055/s-0029-1219382

  日期：2010.3

  Inspired by the unexpected reactivity of desulfated naturally occurring glucoraphenin, methods to synthesize thioimidate N-oxides (TIO) have been devised on simple or carbohydrate templates. Either through halocyclization or under Mitsunobu conditions, the starting thiohydroximates cyclized to generate efficiently the corresponding TIO.

  受天然存在的脱硫脂肪草的意外反应性的启发，已经设计了在简单或碳水化合物模板上的硫亚胺N-氧化物（TIO）的合成方法。无论是通过卤环化还是米特松布条件，起始的硫醇肟会环化以高效生成相应的TIO。
• Nagashima; Uchiyama, Nippon Nogeikagaku Kaishi, 1959, vol. 33, p. 1068,1069
  作者：Nagashima、Uchiyama

  DOI：——

  日期：——
• Rapid and Efficient Desulfonation Method for the Analysis of Glucosinolates by High-Resolution Liquid Chromatography Coupled with Quadrupole Time-of-Flight Mass Spectrometry
  作者：Jashbir Singh、Guddadarangavvanahally K. Jayaprakasha、Bhimanagouda S. Patil

  DOI：10.1021/acs.jafc.7b04662

  日期：2017.12.20

  The goal of our present research was to develop a simple and rapid method for the quantitation of desulfoglucosinolates (desulfoGLS) without using column chromatography. The proposed method involves extraction, concentration, incubation of glucosinolates with a sulfatase enzyme, and HPLC analysis. Identification of desulfoGLS in green kohlrabi was performed by LC-HR-ESI-QTOF-MS in positive-ionization mode. A total of 11 desulfoGLS were identified with neoglucobrassicin (3.32 +/- 0.05 mu mol/g DW) as the predominant indolyl, whereas progoitrin and sinigrin were the major aliphatic desulfoGLS. The levels of the aliphatic desulfoGLS glucoiberin, progoitrin, and glucoerucin at 7 h were found to be 3.6-, 1.9-, and 1.6-fold higher, respectively, than those produced through the conventional method. This technique was successfully applied in the identification of desulfoGLS from cabbage. The developed method has fewer unit operations, has maximum recovery, and is reproducible in the determination of desulfoGLS in a large number of Brassicaceae samples in a short time.
• Fluorinated Phosphoadenosine 5′-Phosphosulfate Analogues for Continuous Sulfotransferase Activity Monitoring and Inhibitor Screening by ¹⁹F NMR Spectroscopy
  作者：Agnieszka Mlynarska-Cieslak、Mikolaj Chrominski、Tomasz Spiewla、Marek R. Baranowski、Marcelina Bednarczyk、Jacek Jemielity、Joanna Kowalska

  DOI：10.1021/acschembio.1c00978

  日期：2022.3.18

  ubiquitous enzymes that participate in a vast number of biological processes involving sulfuryl group (SO3) transfer. 3′-phosphoadenosine 5′-phosphosulfate (PAPS) is the universal ST cofactor, serving as the “active sulfate” source in cells. Herein, we report the synthesis of three fluorinated PAPS analogues that bear fluorine or trifluoromethyl substituents at the C2 or C8 positions of adenine and their

  磺基转移酶 (ST) 是普遍存在的酶，它们参与大量涉及硫酰基 (SO 3 ) 转移的生物过程。3'-磷酸腺苷 5'-磷酸硫酸盐 (PAPS) 是通用的 ST 辅因子，是细胞中的“活性硫酸盐”来源。在这里，我们报告了在腺嘌呤的 C2 或 C8 位置带有氟或三氟甲基取代基的三种氟化 PAPS 类似物的合成，以及它们作为替代辅因子的评估，使 ST 活性能够通过 fluorine-19 核磁进行量化和实时监测。共振( 19 F NMR)光谱。使用植物 AtSOT18 和人类 SULT1A3 作为两种模型酶，我们揭示了氟化 PAPS 类似物在酶识别和工作方面显示出互补特性。19 F NMR pH 范围，是研究 ST 的有吸引力的多功能工具。最后，我们开发了一种19 F NMR 检测方法，用于筛选针对 SULT1A3 的潜在抑制剂，从而突出了氟化 PAPS 类似物在发现 ST 相关疾病药物中的可能用途。