Boc-Tyr-Weinreb amide | 151133-14-1

• 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: Boc-Tyr-Weinreb amide
• 英文别名: tert-butyl(S)-2-(4-hydroxyphenyl)-1-(methoxy-methyl-carbamoyl)-ethylcarbamate；tert-butyl N-[(2S)-3-(4-hydroxyphenyl)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]carbamate
• CAS: 151133-14-1
• 化学式: C₁₆H₂₄N₂O₅
• 分子量: 324.377
• InChiKey: IYWOYEIPVBCGOG-ZDUSSCGKSA-N

物化性质

• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-Tyr-Weinreb amide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 N-(tert-butyloxycarbonyl)-L-tyrosinal
  参考文献：
  名称：

  Novel cell-penetrating α-keto-amide calpain inhibitors as potential treatment for muscular dystrophy

  摘要：

  Dipeptide-derived alpha-keto-amide compounds with potent calpain inhibitory activity have been identified. These reversible covalent inhibitors have IC50 values down to 25 nM and exhibit greatly improved activity in muscle cells compared to the reference compound MDL28170. Several novel calpain inhibitors have shown positive effects on histological parameters in an animal model of Duchenne muscular dystrophy demonstrating their potential as a treatment option for this fatal disease. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.064
• 作为产物：
  描述：

  Boc-L-酪氨酸 在 咪唑 、 氰基磷酸二乙酯 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.5h， 生成 Boc-Tyr-Weinreb amide
  参考文献：
  名称：

  一种通过立体选择性分子内迈克尔环闭合有效合成 Pseudotheonamide A1 的哌嗪酮片段

  摘要：

  二肽的立体选择性分子内迈克尔环闭合有效地产生了赝酰胺 A1 的哌嗪酮片段，这是一种来自海洋海绵 Theonella swinhoei 的丝氨酸蛋白酶抑制剂。

  DOI：

  10.1246/cl.2002.130

文献信息

• Acetic acid derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US05726185A1

  公开（公告）日：1998-03-10

  Acetic acid derivatives of the formula ##STR1## wherein L, M, T and Q have the significance given in the description, can be used for the treatment or prophylaxis of illnesses which are caused by the binding of adhesive proteins to blood platelets and by blood platelet aggregation and cell-cell adhesion, and are manufactured by cleaving protecting groups in the corresponding protected compounds or by converting the cyano group into the amidino group in corresponding nitriles.

  公式为##STR1##的乙酸衍生物，其中L、M、T和Q的含义如描述中所示，可用于治疗或预防由粘附蛋白结合到血小板以及血小板聚集和细胞间黏附引起的疾病，并且可以通过裂解相应保护化合物中的保护基或将相应腈化合物中的氰基转化为氨基亚甲基基团来制造。
• Universal Peptidomimetics
  作者：Eunhwa Ko、Jing Liu、Lisa M. Perez、Genliang Lu、Amber Schaefer、Kevin Burgess

  DOI：10.1021/ja1071916

  日期：2011.1.26

  This paper concerns peptidomimetic scaffolds that can present side chains in conformations resembling those of amino acids in secondary structures without incurring excessive entropic or enthalpic penalties. Compounds of this type are referred to here as minimalist mimics. The core hypothesis of this paper is that small sets of such scaffolds can be designed to analogue local pairs of amino acids (including noncontiguous ones) in any secondary structure; i.e., they are universal peptidomimetics. To illustrate this concept, we designed a set of four peptidomimetic scaffolds. Libraries based on them were made bearing side chains corresponding to many of the protein-derived amino acids. Modeling experiments were performed to give an indication of kinetic and thermodynamic accessibilities of conformations that can mimic secondary structures. Together, peptidomimetics based on these four scaffolds can adopt conformations that resemble almost any combination of local amino acid side chains in any secondary structure. Universal peptidomimetics of this kind are likely to be most useful in the design of libraries for high-throughput screening against diverse targets. Consequently, data arising from submission of these molecules to the NIH Molecular Libraries Small Molecule Repository (MLSMR) are outlined.
• An expedient conversion of α-amino acids into Weinreb amides using COMU® as a coupling agent
  作者：Elizabeth Tyrrell、Peter Brawn、Mark Carew、Iain Greenwood

  DOI：10.1016/j.tetlet.2010.10.169

  日期：2011.1

  The use of CUM, as a non-hazardous partner, in the coupling of N-protected alpha-amino acids to N-methoxy-N-methylamine to afford the corresponding Weinreb amides is discussed. From a practical point of view the reaction can be monitored visually by virtue of the colour change associated with the conversion of substrates (yellow) into the products (orange). As the by-products of the reaction are conveniently water-soluble the products are isolated relatively pure and with minimal racemisation. These factors coupled with the short reaction time make this a very useful procedure. (c) 2010 Published by Elsevier Ltd.
• Vinyl Sulfones as Mechanism-Based Cysteine Protease Inhibitors
  作者：James T. Palmer、David Rasnick、Jeffrey L. Klaus、Dieter Bromme

  DOI：10.1021/jm00017a002

  日期：1995.8
• Total synthesis of cyclotheonamide A
  作者：Peter Wipf、Hongyong Kim

  DOI：10.1021/jo00073a010

  日期：1993.10

  The potent serine protease inhibitor cyclotheonamide A was prepared in a convergent strategy from D-phenylalanine (D-Phe), vinylogous L-tyrosine (L-Vty), L-diaminopropanoic acid (L-Dpr), L-proline (L-Pro), and a hydroxy acid derivative of L-arginine. Macrocyclic ring closure between the D-Phe and the L-Vty residues was performed via the pentafluorophenyl ester, and the Dess-Martin periodinane was used for the oxidation of the hydroxyamide to the alpha-ketoarginine (L-Kar) residue.