(4-mercaptophenyl)methylphosphonic acid | 1025505-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 英文名称: (4-mercaptophenyl)methylphosphonic acid
• 英文别名: 4-mercaptobenzylphosphonic acid；MBPA；(4-Mercaptobenzyl)phosphonic acid；(4-sulfanylphenyl)methylphosphonic acid
• CAS: 1025505-64-9
• 化学式: C₇H₉O₃PS
• 分子量: 204.186
• InChiKey: SPKNHIIOHPFFPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-mercaptophenyl)methylphosphonic acid 、 (3S)-3-amino-4-[[2-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(2S)-1-[[(1S)-1-[4-[[(1S)-1-[4-[[2-[4-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]carbamoyl]-N-(2-sulfanylethyl)anilino]-2-oxoethyl]carbamoyl]-1,3-thiazol-2-yl]-2-hydroxyethyl]carbamoyl]-1,3-thiazol-2-yl]-3-methylbutyl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-4-oxobutanoic acid 在 三(2-羰基乙基)磷盐酸盐 作用下， 以 N-甲基吡咯烷酮 、 水 为溶剂， 反应 72.0h， 以63%的产率得到2-[(2S,9S,12S,15S,21S,24S,30S)-12-[3-(diaminomethylideneamino)propyl]-2-(hydroxymethyl)-21-(1H-imidazol-5-ylmethyl)-9,24-bis(2-methylpropyl)-4,11,14,20,23,26,29,32,35-nonaoxo-7,38-dithia-3,10,13,19,22,25,28,31,34,39,40-undecazatetracyclo[34.2.1.15,8.015,19]tetraconta-1(39),5,8(40),36-tetraen-30-yl]acetic acid
  参考文献：
  名称：

  使用 4-巯基苄基膦酸对 N-Sulfanylethylanilide 肽进行无半胱氨酸分子内连接：合成环肽三甲酰胺

  摘要：

  开发了基于 N-硫基乙基苯胺 (SEAlide) 的连接，用于制备三甲酰胺，这是一种从形成开花的蓝细菌 Trichodesmium erythraeum 中分离出的含噻唑环肽。在这种不含半胱氨酸的连接中，4-巯基苄基膦酸 (MBPA) 作为双启动子，用于 N-S 酰基转移介导的 SEAlide 单元的激活和随后的连接。此外，我们使用一锅 Hantzsch 工艺建立了对映异构纯噻唑氨基酸的高产路线。

  DOI：

  10.1055/s-0036-1589055
• 作为产物：
  描述：

  diethyl [4-(acetylthio)phenyl]methylphosphonate 在 盐酸 作用下， 反应 5.0h， 以83%的产率得到(4-mercaptophenyl)methylphosphonic acid
  参考文献：
  名称：

  Rate enhancement of the oxidative folding of lysozyme by the use of aromatic thiol containing redox buffers

  摘要：

  Almost all therapeutic proteins and most extracellular proteins contain disulfide bonds. The production of these proteins in bacteria or in vitro is challenging due to the need to form the correctly matched disulfide bonds during folding. One important parameter for efficient in vitro folding is the composition of the redox buffer, a mixture of a small molecule thiol and small molecule disulfide. The effects of different redox buffers on protein folding, however, have received limited attention. The oxidative folding of denatured reduced lysozyme was followed in the presence of redox buffers containing varying concentrations of five different aromatic thiols or the traditional aliphatic thiol glutathione (GSH). Aromatic thiols eliminated the lag phase at low disulfide concentrations, increased the folding rate constant up to 11-fold, and improved the yield of active protein relative to GSH. The yield of active protein was similar for four of the five aromatic thiols and for glutathione at pH 7 as well as for glutathione at pH 8.2. At pH 6 the positively charged aromatic thiol provided a higher yield than the negatively charged thiols. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.047
• 作为试剂：
  描述：

  在 (4-mercaptophenyl)methylphosphonic acid 、 三(2-羰基乙基)磷盐酸盐 作用下， 以 N-甲基吡咯烷酮 、 水 为溶剂， 反应 72.0h， 以65%的产率得到
  参考文献：
  名称：

  使用 4-巯基苄基膦酸对 N-Sulfanylethylanilide 肽进行无半胱氨酸分子内连接：合成环肽三甲酰胺

  摘要：

  开发了基于 N-硫基乙基苯胺 (SEAlide) 的连接，用于制备三甲酰胺，这是一种从形成开花的蓝细菌 Trichodesmium erythraeum 中分离出的含噻唑环肽。在这种不含半胱氨酸的连接中，4-巯基苄基膦酸 (MBPA) 作为双启动子，用于 N-S 酰基转移介导的 SEAlide 单元的激活和随后的连接。此外，我们使用一锅 Hantzsch 工艺建立了对映异构纯噻唑氨基酸的高产路线。

  DOI：

  10.1055/s-0036-1589055

文献信息

• Rate enhancement of the oxidative folding of lysozyme by the use of aromatic thiol containing redox buffers
  作者：Minakshi C. Gurbhele-Tupkar、Lissette R. Perez、Yenia Silva、Watson J. Lees

  DOI：10.1016/j.bmc.2007.11.047

  日期：2008.3

  Almost all therapeutic proteins and most extracellular proteins contain disulfide bonds. The production of these proteins in bacteria or in vitro is challenging due to the need to form the correctly matched disulfide bonds during folding. One important parameter for efficient in vitro folding is the composition of the redox buffer, a mixture of a small molecule thiol and small molecule disulfide. The effects of different redox buffers on protein folding, however, have received limited attention. The oxidative folding of denatured reduced lysozyme was followed in the presence of redox buffers containing varying concentrations of five different aromatic thiols or the traditional aliphatic thiol glutathione (GSH). Aromatic thiols eliminated the lag phase at low disulfide concentrations, increased the folding rate constant up to 11-fold, and improved the yield of active protein relative to GSH. The yield of active protein was similar for four of the five aromatic thiols and for glutathione at pH 7 as well as for glutathione at pH 8.2. At pH 6 the positively charged aromatic thiol provided a higher yield than the negatively charged thiols. (C) 2007 Elsevier Ltd. All rights reserved.
• Cysteine-Free Intramolecular Ligation of N-Sulfanylethylanilide Peptide Using 4-Mercaptobenzylphosphonic Acid: Synthesis of Cyclic Peptide Trichamide
  作者：Akira Otaka、Keisuke Aihara、Tsubasa Inokuma、Takahisa Jichu、Zhenjian Lin、Feixue Fu、Kosuke Yamaoka、Akira Shigenaga、David Hutchins、Eric Schmidt

  DOI：10.1055/s-0036-1589055

  日期：2017.9

  thiazole-containing cyclic peptide isolated from bloom-forming cyanobacterium Trichodesmium erythraeum. In this cysteine-free ligation, 4-mercaptobenzylphosphonic acid (MBPA) functions as a dual promoter both for the N–S acyl-transfer-mediated activation of the SEAlide unit and for subsequent ligation. Furthermore, we established a high-yielding route to enantiomerically pure thiazole amino acids using a one-pot

  开发了基于 N-硫基乙基苯胺 (SEAlide) 的连接，用于制备三甲酰胺，这是一种从形成开花的蓝细菌 Trichodesmium erythraeum 中分离出的含噻唑环肽。在这种不含半胱氨酸的连接中，4-巯基苄基膦酸 (MBPA) 作为双启动子，用于 N-S 酰基转移介导的 SEAlide 单元的激活和随后的连接。此外，我们使用一锅 Hantzsch 工艺建立了对映异构纯噻唑氨基酸的高产路线。