L-[S-(4'-hydroxybenzyl)]cysteine

• 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: L-[S-(4'-hydroxybenzyl)]cysteine
• 英文别名: (2R)-2-amino-3-[(4-hydroxyphenyl)methylsulfanyl]propanoic acid
• 化学式: C₁₀H₁₃NO₃S
• 分子量: 227.284
• InChiKey: FOZPSQNWQKBIGF-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-[S-(4'-hydroxybenzyl)]cysteine 在 双氧水 作用下， 反应 0.5h， 以16.5 mg的产率得到(-)-(S_S)-L-[S-(4-hydrohydroxybenzyl)]cysteine sulfoxide
  参考文献：
  名称：

  4-Hydroxybenzyl-substituted glutathione derivatives fromGastrodia elata

  摘要：

  Seven new 4-hydroxybenzyl-substituted glutathione derivatives (2-8), together with a known analogue (1), were isolated from the aqueous extract of Gastrodia elata Blume rhizomes. Their structures were determined by using spectroscopic and chemical methods. The absolute configurations of 1-8 were assigned by using Marfey's method, combined with comparing the NMR and CD spectroscopic data of sulfoxide moieties in 3-6 with those of S-(4-hydroxybenzyl)cysteine sulfoxide stereoisomers (9-12) synthesized as authentic samples. The configurations of 9-12 were confirmed by electronic CD calculations based on the quantum-mechanical time-dependent density functional theory. Furthermore, the structures of 1, 3, 5, 7, and 8 were verified by synthesis. Compound 3 was active against serum deprivation-induced PC12 cell damage and synthetic 9-14 exhibited activity against Fe2+-cysteine induced rat liver microsomal lipid peroxidation.

  DOI：

  10.1080/10286020.2015.1040000
• 作为产物：
  描述：

  Z(OMe)-Cys(MBzl)-OH 在 甲烷磺酸 、 sodium perborate 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 L-[S-(4'-hydroxybenzyl)]cysteine
  参考文献：
  名称：

  Studies on peptides. LXXXIII. Behavior of S-substituted cysteine sulfoxides under deprotecting conditions in peptide synthesis.

  摘要：

  用过硼酸钠氧化法制备了 Cys（S-对甲氧基苄基）和 Cys（S-苄基）的亚砜。在苯甲醚或苯酚存在下，氟化氢和甲磺酸分别将前一种亚砜转化为 S-对甲氧基苯基半胱氨酸或 S-对羟基苯基半胱氨酸，而后一种亚砜则能抵抗这些脱保护试剂的作用。噻吩酚似乎是保护半胱氨酸亚砜的强力还原试剂。

  DOI：

  10.1248/cpb.27.2151

文献信息

• Moringin and Its Structural Analogues as Slow H₂S Donors: Their Mechanisms and Bioactivity
  作者：Yuyun Lu、Xingyi Wang、Haoliang Pu、Yi Lin、Dan Li、Shao Quan Liu、Dejian Huang

  DOI：10.1021/acs.jafc.0c02358

  日期：2020.7.8

  These isothiocyanates rapidly formed cysteine adducts, which underwent intramolecular cyclization followed by slowly releasing (a) organic amine and raphanusamic acid and (b) H2S and 2-carbylamino-4,5-dihydrothiazole-4-carboxylic acids. The product distributions are highly dependent on para-substituents on the phenyl group. Moringin has higher cytotoxicity to cancer cells and is a more potent anti-inflammatory

  辣木（辣木苄基异硫氰酸酯）是辣木种子中的主要生物活性化合物，已被用作健康食品。但是，其生物活性机制尚不十分清楚。我们研究了moringin及其结构相似的类似物，包括异硫氰酸苄酯和4-羟基异硫氰酸苄酯，其半胱氨酸引发的硫化氢（H 2 S）释放活性。这些异硫氰酸酯迅速形成半胱氨酸加合物，将其进行分子内环化，然后缓慢释放（a）有机胺和萝卜酸和（b）H 2S和2-羰基氨基-4,5-二氢噻唑-4-羧酸。产物分布高度依赖于苯基上的对位取代基。辣木素对癌细胞具有更高的细胞毒性，并且是比苄基和羟基苄基类似物更有效的抗炎剂，而异硫氰酸苄酯是一种更好的抗菌剂。两者合计，它们的生物活性可能与它们的H 2 S供体活性没有直接关系。但是，仅其他代谢物不具有细胞毒性和抗炎活性。这些发现表明，它们的活性可能是不同代谢物通过竞争途径以及苄基ITC的对位取代基的组合效应。
• Metabolic Activation of Militarine In Vitro and In Vivo
  作者：Ying Zou、Yang Wang、Kunna Li、Mengyue Zhou、Jing Li、Xu Wang、Rong Tan、Chutian Wu、Ying Liu、Weiwei Li、Jiang Zheng

  DOI：10.1021/acs.chemrestox.1c00430

  日期：2022.5.16

  Bletilla striata is consumed as food and herbal medicine. Militarine (MLT) is a major ingredient in B. striata. Previous studies demonstrated that MLT showed teratogenic toxicity to zebrafish embryos. The present study aimed to identify reactive metabolites possibly involved in the cytotoxicity of MLT and determine the metabolic pathways involved. MLT was found to be hydrolyzed to p-hydroxybenzyl alcohol (HBA) by β-glucosidase and esterases. The resulting HBA further underwent spontaneous dehydration to form quinone methide. HBA was also metabolized to the corresponding sulfate, followed by departure of the sulfate to generate a quinone methide. The resultant quinone methide reacted with hepatic glutathione (GSH) and protein to form the corresponding GSH conjugate and protein adduction. Additionally, inhibition of sulfotransferases (SULTs) attenuated the susceptibility of hepatocytes to the toxicity of MLT. This study provides that the hydrolytic enzymes β-glucosidase, esterases, and SULTs participate in the metabolic activation of MLT.

  Bletilla striata 可作为食物和草药食用。米利他林（MLT）是条纹叶莼的主要成分。先前的研究表明，MLT 对斑马鱼胚胎有致畸毒性。本研究旨在找出可能与 MLT 的细胞毒性有关的活性代谢物，并确定其中涉及的代谢途径。研究发现，MLT 会被β-葡萄糖苷酶和酯酶水解为对羟基苯甲醇（HBA）。生成的 HBA 会进一步自发脱水，形成醌甲醚。HBA 也被代谢为相应的硫酸盐，然后硫酸盐离开生成甲脒醌。生成的甲脒醌与肝脏谷胱甘肽（GSH）和蛋白质反应，形成相应的谷胱甘肽共轭物和蛋白质加合物。此外，抑制磺基转移酶（SULTs）可减轻肝细胞对 MLT 毒性的敏感性。这项研究表明，β-葡萄糖苷酶、酯酶和 SULTs 等水解酶参与了 MLT 的代谢活化过程。
• Thermally Sensitive Protecting Groups for Cysteine for Peptide Cyclization and Selective Disulfide Bond Formation
  申请人：University of Windsor

  公开号：US20220153749A1

  公开（公告）日：2022-05-19

  In a preferred embodiment, there is provided a protecting group for protecting the thiol side chain of a cysteine residue, the protecting group comprising a Diels-Alder cycloadduct of a furan and a maleimide, and optionally, a linker interposed between the thiol side chain and the Diels-Alder cycloadduct.
• Studies on peptides. LXXXIII. Behavior of S-substituted cysteine sulfoxides under deprotecting conditions in peptide synthesis.
  作者：SUSUMU FUNAKOSHI、NOBUTAKA FUJII、KENICHI AKAJI、HIROSHI IRIE、HARUAKI YAJIMA

  DOI：10.1248/cpb.27.2151

  日期：——

  Sulfoxides of Cys (S-p-methoxybenzyl) and Cys (S-benzyl) were prepared by oxidation with sodium perborate. Hydrogen fluoride and methanesulfonic acid converted the former sulfoxide to S-p-methoxyphenylcysteine or S-p-hydroxyphenylcysteine in the presence of anisole or phenol, respectively, while the latter sulfoxide resisted the actions of these deprotecting reagents. Thiophenol appears to be useful as a powerful reducing reagent for protected cysteine sulfoxides.

  用过硼酸钠氧化法制备了 Cys（S-对甲氧基苄基）和 Cys（S-苄基）的亚砜。在苯甲醚或苯酚存在下，氟化氢和甲磺酸分别将前一种亚砜转化为 S-对甲氧基苯基半胱氨酸或 S-对羟基苯基半胱氨酸，而后一种亚砜则能抵抗这些脱保护试剂的作用。噻吩酚似乎是保护半胱氨酸亚砜的强力还原试剂。
• 4-Hydroxybenzyl-substituted glutathione derivatives from<i>Gastrodia elata</i>
  作者：Qing-Lan Guo、Ya-Nan Wang、Cheng-Gen Zhu、Ming-Hua Chen、Zhi-Bo Jiang、Nai-Hong Chen、Xiu-Yun Song、Mei-Jin Zhang、Jian-Gong Shi

  DOI：10.1080/10286020.2015.1040000

  日期：2015.5.4

  Seven new 4-hydroxybenzyl-substituted glutathione derivatives (2-8), together with a known analogue (1), were isolated from the aqueous extract of Gastrodia elata Blume rhizomes. Their structures were determined by using spectroscopic and chemical methods. The absolute configurations of 1-8 were assigned by using Marfey's method, combined with comparing the NMR and CD spectroscopic data of sulfoxide moieties in 3-6 with those of S-(4-hydroxybenzyl)cysteine sulfoxide stereoisomers (9-12) synthesized as authentic samples. The configurations of 9-12 were confirmed by electronic CD calculations based on the quantum-mechanical time-dependent density functional theory. Furthermore, the structures of 1, 3, 5, 7, and 8 were verified by synthesis. Compound 3 was active against serum deprivation-induced PC12 cell damage and synthetic 9-14 exhibited activity against Fe2+-cysteine induced rat liver microsomal lipid peroxidation.