D-S-叔丁基半胱氨酸 | 2481-10-9

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 半胱氨酸类衍生物
• 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: D-S-叔丁基半胱氨酸
• 中文别名: (R)-2-氨基-3-(叔丁基硫)丙酸
• 英文名称: S-tert.-Butyl-L-cystein
• 英文别名: H-Cys(t-Bu)-OH；(2R)-2-amino-3-tert-butylsulfanylpropanoic acid
• CAS: 2481-10-9
• 化学式: C₇H₁₅NO₂S
• 分子量: 177.268
• InChiKey: VADVRIAPCDFQJU-YFKPBYRVSA-N

物化性质

• 熔点：
  193 °C (decomp)
• 沸点：
  293.5±35.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  D-S-叔丁基半胱氨酸 在 甲基三氯硅烷 、 二苯基亚砜 作用下， 反应 0.17h， 以99%的产率得到L-胱氨酸
  参考文献：
  名称：

  使用二氯化硅-亚砜系统通过新的二硫键形成反应合成胱氨酸肽

  摘要：

  在二苯基亚砜存在下，在三氟乙酸中的甲基三氯硅烷或四氯硅烷可通过还原-氧化反应裂解半胱氨酸的各种S保护基团，直接形成胱氨酸。这种新的二硫键形成反应已成功应用于催产素和人脑利钠肽的合成。

  DOI：

  10.1039/c39910000167
• 作为产物：
  描述：

  S-tert-Butyl-N-acetyl-L-cysteine 在 pig kidney acylase I 作用下， 以 phosphate buffer 为溶剂， 反应 0.17h， 生成 D-S-叔丁基半胱氨酸
  参考文献：
  名称：

  Acylase I-Catalyzed Deacetylation of N-Acetyl-l-cysteine and S-Alkyl-N-acetyl-l-cysteines

  摘要：

  The aminoacylase that catalyzes the hydrolysis of N-acetyl-L-cysteine (NAC) was identified as acylase I after purification by column chromatography and electrophoretic analysis. Rat kidney cytosol was fractionated by ammonium sulfate precipitation, and the proteins were separated by ion-exchange column chromatography, gel-filtration column chromatography, and hydrophobic interaction column chromatography. Acylase activity with NAC and N-acetyl-L-methionine (NAM), a known substrate for acylase I, as substrates coeluted during all chromatographic steps. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis showed that the protein was purified to near homogeneity and had a subunit M-r of 43 000, which is identical with the M-r of acylase I from porcine kidney and bovine liver. n-Butylmalonic acid was a slow-binding inhibitor of acylase I and inhibited the deacetylation of NAC with a K-i of 192 +/- 27 mu M These results show that acylase I catalyzes the deacetylation of NAG. The acylase I-catalyzed deacetylation of a range of S-alkyl-N-acetyl-L-cysteines, their carbon and oxygen analogues, and the selenium analogue of NAM was also studied with porcine kidney acylase I. The specific activity of the acylase I-catalyzed deacetylation of these substrates was related to their calculated molar volumes and lag P values. The S-alkyl-N-acetyl-L-cysteines with short (C-0-C-3) and unbranched S-alkyl substituents were good acylase I substrates, whereas the S-alkyl-N-acetyl-L-cysteines with long (>C-3) and branched S-alkyl substituents were poor acylase I substrates. The carbon and oxygen analogues of S-methyl-N-acetyl-L-cysteine and the carbon analogue of S-ethyl-N-acetyl-L-cysteine were poor acylase I substrates, whereas the selenium analogue of NAM was a good acylase I substrate.

  DOI：

  10.1021/tx980018b

文献信息

• Process for producing alpha-aminoketones
  申请人：AJINOMOTO CO., INC.

  公开号：US20020035288A1

  公开（公告）日：2002-03-21

  A process for producing &agr;-aminohalomethyl ketones or N-protected &agr;-aminohalomethyl ketones from specified 3-oxazolidin-5-one derivatives via 5-halomethyl-5-hydroxy-3-oxazolidine derivatives. By this process, &agr;-aminohalomethyl ketones and compounds relating to them can be obtained efficiently and economically in industrial scale.

  从指定的3-噁唑烷-5-酮衍生物通过5-卤甲基-5-羟基-3-噁唑烷衍生物制备α-氨基卤甲基酮或N-保护的α-氨基卤甲基酮的过程。通过这个过程，可以在工业规模上高效经济地获得α-氨基卤甲基酮及相关化合物。
• S-t-BUTYL PROTECTED CYSTEINE DI-PEPTIDE ANALOGS AND RELATED COMPOUNDS
  申请人：Johnson, II Edward M.

  公开号：US20120122792A1

  公开（公告）日：2012-05-17

  S-t-butyl protected cysteine di-peptide analogs and related compounds and methods of using these compounds for the treatment of diseases and/or conditions, including but not limited to diseases and/or conditions of Central Nervous System (CNS).

  S-叔丁基保护的半胱氨酸二肽类似物和相关化合物以及使用这些化合物治疗疾病和/或症状的方法，包括但不限于中枢神经系统（CNS）疾病和/或症状。
• Compounds exhibiting thrombopoietin-like activities
  申请人：——

  公开号：US20030162724A1

  公开（公告）日：2003-08-28

  The compounds of the invention are compounds represented by the following general formula (1): 1 wherein E represents one selected from the group consisting of a methylidyne group and a nitrilo group, R 1 represents one selected from the group consisting of optionally substituted aryl groups and optionally substituted heteroaryl groups, R 2 represents one selected from the group consisting of a hydrogen atom and alkyl groups, W 1 represents an amino acid residue, A represents one selected from the group consisting of a carbonyl group and a sulfonyl group, X 1 represents one selected from the group consisting of optionally substituted alkylene groups and optionally substituted alkenylene groups, and p represents 0 or 1; and their pharmacologically acceptable salts, which exhibit thrombopoietin-like activity.

  本发明的化合物是由以下一般式（1）表示的化合物：其中E代表从甲基亚基团和硝基亚基团组成的群体中选择的一种，R1代表从可选择的取代芳基和可选择的取代杂环烷基组成的群体中选择的一种，R2代表从氢原子和烷基组成的群体中选择的一种，W1代表氨基酸残基，A代表从羰基和磺酰基组成的群体中选择的一种，X1代表从可选择的取代烷基烯基团和可选择的取代烯基烷基团组成的群体中选择的一种，p代表0或1；以及它们的药理学上可接受的盐，具有类似于血小板生成素的活性。
• Method for producing epoxide crystal
  申请人：Ajinomoto Co., Inc.

  公开号：US20020072621A1

  公开（公告）日：2002-06-13

  The invention relates to a method for industrially producing highly pure (2R, 3S)- or (2S, 3R)-N-carbamate-protected &bgr;-aminoepoxide (crystal) or (2R, 3S)- or (2S, 3R)-N-carbamate-protected &bgr;-aminoalcohol. The method for producing N-carbamate-protected &bgr;-aminoepoxide crystal, includes one or more of the following steps (a) to (d): (a) dissolving (2R, 3S)- or (2S, 3R)-N-carbamate-protected &bgr;-aminoalcohol containing at least the diastereomer as an impurity in a solvent including at least one or more selected from aromatic hydrocarbon solvent, saturated hydrocarbon solvent, aqueous mixture solvent, acetone and 2-propanol, to remove insoluble matters; (b) treating the (2R, 3S)- or (2S, 3R)-N-carbamate-protected &bgr;-aminoalcohol with a base, thereby converting the N-carbamate-protected &bgr;-aminoalcohol to (2R, 3S)- or (2S, 3R)-N-carbamate-protected &bgr;-aminoepoxide; (c) treating the (2R, 3S)- or (2S, 3R)-N-carbamate-protected &bgr;-aminoepoxide containing at least the diastereomer as an impurity with an acid, thereby converting the diastereomer as an impurity to (4S, 5R) or (4R, 5S) oxazolidin-2-one derivative, and optionally separating and removing the resulting oxazolidin-2-one derivative in water or an aqueous mixture solvent; and (d) crystallizing the (2R, 3S)- or (2S, 3R)-N-carbamate-protected &bgr;-aminoepoxide in a mixture solvent of water and water-miscible organic solvent. By the methods of the present invention, highly pure (2R, 3S)- or (2S, 3R)-N-carbamate-protected &bgr;-aminoepoxide or (2R, 3S) or (2S, 3R)-N-carbamate-protected &bgr;-aminoalcohol can be efficiently produced.

  该发明涉及一种工业生产高纯度(2R, 3S)或(2S, 3R)-N-碳酸酯保护的β-氨基环氧乙烷(晶体)或(2R, 3S)或(2S, 3R)-N-碳酸酯保护的β-氨基醇的方法。生产N-碳酸酯保护的β-氨基环氧乙烷晶体的方法包括以下一项或多项步骤(a)至(d)：(a)将至少含有对映异构体作为杂质的(2R, 3S)或(2S, 3R)-N-碳酸酯保护的β-氨基醇溶解于包括至少选择自芳香烃溶剂、饱和烃溶剂、水混合溶剂、丙酮和异丙醇的溶剂中，以去除不溶物质；(b)用碱处理(2R, 3S)或(2S, 3R)-N-碳酸酯保护的β-氨基醇，从而将N-碳酸酯保护的β-氨基醇转化为(2R, 3S)或(2S, 3R)-N-碳酸酯保护的β-氨基环氧乙烷；(c)用酸处理至少含有对映异构体作为杂质的(2R, 3S)或(2S, 3R)-N-碳酸酯保护的β-氨基环氧乙烷，从而将对映异构体作为杂质转化为(4S, 5R)或(4R, 5S)噁唑烷-2-酮衍生物，并可在水或水混合溶剂中分离和去除所得的噁唑烷-2-酮衍生物；(d)在水和水亲和性有机溶剂的混合溶剂中结晶(2R, 3S)或(2S, 3R)-N-碳酸酯保护的β-氨基环氧乙烷。通过本发明的方法，可以高效生产高纯度的(2R, 3S)或(2S, 3R)-N-碳酸酯保护的β-氨基环氧乙烷或(2R, 3S)或(2S, 3R)-N-碳酸酯保护的β-氨基醇。
• Facile Chemoselective Synthesis of Dehydroalanine-Containing Peptides
  作者：Nicole M. Okeley、Yantao Zhu、Wilfred A. van der Donk

  DOI：10.1021/ol006485d

  日期：2000.11.1

  for the synthesis of dehydroalanine residues (II) within peptides. The unnatural amino acid (Se)-phenylselenocysteine (I) can be incorporated into growing peptide chains via standard peptide synthesis procedures. Subsequent oxidative elimination affords a dehydroalanine at the desired position. The oxidation conditions are mild and tolerate functionalities commonly found in peptides, including variously

  描述了用于合成肽内的脱氢丙氨酸残基（II）的有用方法。非天然氨基酸（Se）-苯基硒代半胱氨酸（I）可以通过标准的肽合成方法掺入生长中的肽链中。随后的氧化消除在所需位置提供脱氢丙氨酸。氧化条件温和且可耐受肽中常见的功能，包括各种保护的半胱氨酸残基。为了说明其实用性，已经通过这种方法合成了环状羊毛硫氨酸。