tert-butyl 2(S)-tert-butoxycarbonylamino-4-methylsulfonyloxybutyrate | 168264-01-5

• 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: tert-butyl 2(S)-tert-butoxycarbonylamino-4-methylsulfonyloxybutyrate
• 英文别名: tert-butyl (2S)-2-(tert-butoxycarbonylamino)-4-(methanesulfonyloxy)butanoate；tert-butyl (S)-2-(tert-butoxycarbonylamino)-4-(methanesulfonyloxy)butanoate；N-[(1,1-Dimethylethoxy)carbonyl]-L-homoserine 1,1-Dimethylethyl Ester Methanesulfonate；tert-butyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-methylsulfonyloxybutanoate
• CAS: 168264-01-5
• 化学式: C₁₄H₂₇NO₇S
• 分子量: 353.437
• InChiKey: CFEGMMGSUXRCGC-JTQLQIEISA-N

物化性质

• 熔点：
  85-87 °C
• 沸点：
  493.5±40.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿；二氯甲烷；乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl 2(S)-tert-butoxycarbonylamino-4-methylsulfonyloxybutyrate 在 sodium bromide 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以1.5 g的产率得到tert-butyl 4-bromo-2S-butoxycarbonylaminobutyrate
  参考文献：
  名称：

  三氟硒代蛋氨酸：一种新的非天然氨基酸

  摘要：

  氟化氨基酸：三氟硒代蛋氨酸是一种新的非天然氨基酸，相对于硒代蛋氨酸，对人类结肠癌细胞表现出增强的蛋氨酸酶诱导的细胞毒性。令人惊讶的是，给予9:1三氟硒代蛋氨酸/蛋氨酸的大肠杆菌主要提供含有硒代蛋氨酸单元的蛋白质。大肠杆菌中三氟甲基的去除是通过酶催化的。

  DOI：

  10.1002/cbic.201600266
• 作为产物：
  描述：

  (S)-2-tert-Butoxycarbonylamino-succinic acid 1-tert-butyl ester; compound with dicyclohexyl-amine 在 盐酸 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 tert-butyl 2(S)-tert-butoxycarbonylamino-4-methylsulfonyloxybutyrate
  参考文献：
  名称：

  Synthesis and Structure Activity Relationships of a Novel Antifungal Agent, Azoxybacilin.

  摘要：

  一种新的抗真菌物质，阿唑氧巴西林（一种带有阿唑氧基部分的不规则氨基酸）及其衍生物已通过Moss方法从Boc-L-Asp-OtBu合成，旨在制备阿唑氧基部分。酯衍生物Ro 09-1824显示出比阿唑氧巴西林更强的抗真菌活性和更广泛的抗真菌谱。

  DOI：

  10.1248/cpb.42.1703

文献信息

• Inhibitors of nicotinamide N-methyltransferase designed to mimic the methylation reaction transition state
  作者：Matthijs J. van Haren、Rebecca Taig、Jilles Kuppens、Javier Sastre Toraño、Ed E. Moret、Richard B. Parsons、Davide Sartini、Monica Emanuelli、Nathaniel I. Martin

  DOI：10.1039/c7ob01357d

  日期：——

  inhibitors derived from the structures of the substrates involved in the methylation reaction. By covalently linking fragments of the NNMT substrates a diverse library of bisubstrate-like compounds was prepared. The ability of these compounds to inhibit NNMT was evaluated providing valuable insights into the structural tolerances of the enzyme active site. These studies led to the identification of new

  烟酰胺N-甲基转移酶（NNMT）是一种催化烟酰胺甲基化以形成N的酶′-甲基烟酰胺。NNMT及其甲基化产物最近都与多种疾病有关，这表明该酶作为其治疗目标的作用已超出其先前在排毒中赋予的代谢功能。我们在这里描述了来自参与甲基化反应的底物结构的NNMT抑制剂的系统开发。通过共价连接NNMT底物的片段，制备了多种双底物样化合物库。评估了这些化合物抑制NNMT的能力，为了解酶活性位点的结构耐受性提供了宝贵的见识。
• Synthesis and evaluation of tripeptidic plasmin inhibitors with nitrile as warhead
  作者：Naoki Teno、Tadamune Otsubo、Keigo Gohda、Keiko Wanaka、Takuya Sueda、Kiyoshi Ikeda、Akiko Hijikata-Okunomiya、Yuko Tsuda

  DOI：10.1002/psc.2442

  日期：2012.10

  triggered by plasmin. On the basis of the peptidic sequence derived from the synthetic plasmin substrate, a series of peptidic plasmin inhibitors possessing nitrile as warhead were prepared and evaluated for their inhibitory activities against plasmin and other serine proteases, plasma kallikrein and urokinase. The most potent peptidic inhibitors with the nitrile warhead exhibit the potency toward plasmin

  纤溶酶是纤溶系统中的关键分子，众所周知，纤溶酶对血块溶解至关重要，并且可以引发基质金属蛋白酶（MMP）激活级联反应。建议纤溶酶与MMP一起参与与癌症形成风险相关的生理过程。纤溶酶抑制剂可被视为治疗纤溶酶引发的疾病的有希望的新原理。根据合成纤溶酶底物的肽序列，制备了一系列以腈为战斗部的肽纤溶酶抑制剂，并评价了它们对纤溶酶和其他丝氨酸蛋白酶，血浆激肽释放酶和尿激酶的抑制活性。具有腈弹头的最强肽抑制剂对纤溶酶具有有效作用（IC 50 = 7.7-11μM），并且具有针对血浆激肽释放酶和尿激酶的选择性。与纤溶酶复合的肽类抑制剂的结果和分子模型表明，P2残基与包含纤溶酶S2和S3亚位点的开放结合袋形成了良好的接触。版权所有©2012欧洲肽协会和John Wiley＆Sons，Ltd.
• Synthesis of meta-Carboranyl-(S)-homocysteine Sulfoxide
  作者：D. A. Gruzdev、V. O. Ustinova、G. L. Levit、V. A. Ol’shevskaya、V. P. Krasnov

  DOI：10.1134/s1070428018100251

  日期：2018.10

  New (S)-homocysteine derivatives containing a meta-carborane fragment were synthesized. m-Carboranyl-(S)-homocysteine sulfoxide was obtained as a mixture of diastereoisomers. The reduction of the side-chain carboxy group of N-tert-butoxycarbonyl-(S)-aspartic acid -tert-butyl ester with sodium tetrahydridoborate was not accompanied by racemization.
• α-Functionalized Phosphonylphosphinates:  Synthesis and Evaluation as Transcarbamoylase Inhibitors
  作者：Alexander Flohr、Andreas Aemissegger、Donald Hilvert

  DOI：10.1021/jm991008q

  日期：1999.7.1

  Diverse alpha-methyl-substituted phosphonylphosphinates (P-C-P-C-X) are accessible from a protected, pentafluorophenylsulfonated phosphonylphosphinate via nucleophilic displacement. The utility of this route is demonstrated with several nitrogen nucleophiles. The resulting amine and amino acid phosphonylphosphinate derivatives were evaluated as inhibitors of Streptococcus faecalis ornithine transcarbamoylase (OTC). Compared with the structurally related phosphonoacetyl-L-ornithine (L-PALO), a known inhibitor of OTCs from various sources, the phosphonylphosphinates are surprisingly poor inhibitors, binding several orders of magnitude less tightly to the enzyme. These results suggest that the tetrahedral intermediate formed in the normal transcarbamoylase reaction is poorly mimicked by a tetrahedral and anionic phosphonate, either because of directly unfavorable interactions with a hydrogen-bond acceptor within the active site or because transition-state analogues are unable to induce the protein conformation changes that normally accompany reaction.