(2S)-2-氨基-3-甲基-3-亚磺酸基丁酸 | 23315-18-6

• 物质功能分类: 有机原料 - 氨基化合物 - 磺酸类氨基化合物
• 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: (2S)-2-氨基-3-甲基-3-亚磺酸基丁酸
• 英文名称: D-Penicillaminsulfinsaeure
• 英文别名: (2S)-2-Amino-3-methyl-3-sulfinobutanoic acid
• CAS: 23315-18-6
• 化学式: C₅H₁₁NO₄S
• 分子量: 181.213
• InChiKey: SVIZNTHNFAOGAB-VKHMYHEASA-N

物化性质

• 沸点：
  429.7±55.0 °C(Predicted)
• 密度：
  1.551±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于酸性水溶液（轻微）、DMSO（轻微）、甲醇（轻微、超声处理）、水

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  11
• 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：
  120
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 海关编码：
  2930909090
• WGK Germany：
  3

反应信息

• 作为产物：
  描述：

  D-青霉胺二硫化物 以 水 为溶剂， 生成 (2S)-2-氨基-3-甲基-3-亚磺酸基丁酸
  参考文献：
  名称：

  γ-Radiolysis of disulfides in aqueous solution. II. D-Penicillamine disulfide

  摘要：

  D-青霉胺二硫化物（PenSSPen）在3×10⁻⁴ M水溶液中的γ-辐解在通气和脱气条件下进行了研究。对以下产物确定了G值：青霉胺亚砜酸（PenSO₂H）、青霉胺酸（PenSO₃H）、β-羟基缬氨酸（PenOH）、2-氨基-3-甲基丁-3-烯酸（HOOC•CH(NH₂)•C(CH₃)=CH₂）、青霉胺（PenSH）、青霉胺二硫化物-S-一氧化物（PenS(O)SPen）、缬氨酸（PenH）、青霉胺三硫化物（PenSSSPen）和氨。在通气溶液中PenSO₃H的低产率表明PenSOH没有与氧气或O₂⁻反应。高产率得到的三硫化物主要来自以下反应：[Formula: see text]。用•OH自由基（TiCl₃/H₂O₂）产生的化学实验和存在半胱氨酸或青霉胺的辐照用于确认这些反应。这些以及其他反应经过了自由基清除剂的测试；甲酸盐和单氯乙酸盐以及一氧化氮。

  DOI：

  10.1139/v69-162

文献信息

• Steady-state substrate specificity and O2-coupling efficiency of mouse cysteine dioxygenase
  作者：Wei Li、Brad S. Pierce

  DOI：10.1016/j.abb.2014.11.004

  日期：2015.1

  Cysteine dioxygenase (CDO) is a non-heme mononuclear iron enzyme that catalyzes the oxygendependent oxidation of L-cysteine (Cys) to produce L-cysteine sulfinic acid (CSA). Sequence alignment of mammalian COO with recently discovered thiol dioxygenase enzymes suggests that the mononuclear iron site within all enzymes in this class share a common 3-His first coordination sphere. This implies a similar mechanistic paradigm among thiol dioxygenase enzymes. Although steady-state studies were first reported for mammalian CDO over 45 years ago, detailed analysis of the specificity for alternative thiol-bearing substrates and their oxidative coupling efficiencies have not been reported for this enzyme. Assuming a similar mechanistic theme among this class of enzymes, characterization of the CDO substrate specificity may provide valuable insight into substrate-active site intermolecular during thiol oxidation. In this work, the substrate-specificity for wild-type Mus musculus CDO was investigated using NMR spectroscopy and LC-MS for a variety of thiol-bearing substrates. Tandem mass spectrometry was used to confirm dioxygenase activity for each non-native substrate investigated. Steady-state MichaelisMenten parameters for sulfinic acid product formation and O-2-consumption were compared to establish the coupling efficiency for each reaction. In light of these results, the minimal substrate requirements for CDO catalysis and O-2-activation are discussed. (C) 2014 Elsevier Inc. All rights reserved.
• γ-Radiolysis of disulfides in aqueous solution. II. <scp>D</scp>-Penicillamine disulfide
  作者：J. W. Purdie

  DOI：10.1139/v69-162

  日期：1969.3.15

  The γ-radiolysis of D-penicillamine disulfide (PenSSPen) in 3 × 10⁻⁴ M aqueous solution has been studied under aerated and deaerated conditions. G values were determined for the following products: penicillamine sulfinic acid (PenSO₂H), penicillaminic acid (PenSO₃H), β-hydroxyvaline (PenOH), 2-amino-3-methylbut-3-enoic acid (HOOC•CH(NH₂)•C(CH₃)=CH₂), penicillamine (PenSH), penicillamine disulfide-S-monoxide (PenS(O)SPen), valine (PenH), penicillamine trisulfide (PenSSSPen), and ammonia. The low yield of PenSO₃H in aerated solution indicated that PenSOH did not react with oxygen or O₂⁻. The trisulfide, which was obtained in high yield, was found to come mainly from the reactions:[Formula: see text]Experiments with •OH radicals produced chemically (TiCl₃/H₂O₂) and irradiations with cysteine or penicillamine present were used to confirm these reactions. These and the other reactions were tested with radical scavengers; formate and monochloroacetate ions and nitrous oxide.

  D-青霉胺二硫化物（PenSSPen）在3×10⁻⁴ M水溶液中的γ-辐解在通气和脱气条件下进行了研究。对以下产物确定了G值：青霉胺亚砜酸（PenSO₂H）、青霉胺酸（PenSO₃H）、β-羟基缬氨酸（PenOH）、2-氨基-3-甲基丁-3-烯酸（HOOC•CH(NH₂)•C(CH₃)=CH₂）、青霉胺（PenSH）、青霉胺二硫化物-S-一氧化物（PenS(O)SPen）、缬氨酸（PenH）、青霉胺三硫化物（PenSSSPen）和氨。在通气溶液中PenSO₃H的低产率表明PenSOH没有与氧气或O₂⁻反应。高产率得到的三硫化物主要来自以下反应：[Formula: see text]。用•OH自由基（TiCl₃/H₂O₂）产生的化学实验和存在半胱氨酸或青霉胺的辐照用于确认这些反应。这些以及其他反应经过了自由基清除剂的测试；甲酸盐和单氯乙酸盐以及一氧化氮。