(S)-methyl 2-((S)-2-amino-6-((tert-butoxycarbonyl)amino)hexanamido)-3-methylbutanoate | 174080-11-6

• 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: (S)-methyl 2-((S)-2-amino-6-((tert-butoxycarbonyl)amino)hexanamido)-3-methylbutanoate
• 英文别名: H-Lys(Boc)-Val-OMe；methyl (2S)-2-[[(2S)-2-amino-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]amino]-3-methylbutanoate
• CAS: 174080-11-6
• 化学式: C₁₇H₃₃N₃O₅
• 分子量: 359.466
• InChiKey: PWNJRURGAAKSSM-STQMWFEESA-N

物化性质

• 沸点：
  517.3±50.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-((S)-2-amino-6-((tert-butoxycarbonyl)amino)hexanamido)-3-methylbutanoate 在 二乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (S)-2-{(S)-2-[(R)-2-[(S)-2-Amino-3-(4-tert-butoxy-phenyl)-propionylamino]-3-(1H-indol-3-yl)-propionylamino]-6-tert-butoxycarbonylamino-hexanoylamino}-3-methyl-butyric acid methyl ester
  参考文献：
  名称：

  Somatostatin Receptor-Binding Peptides Labeled with Technetium-99m:  Chemistry and Initial Biological Studies

  摘要：

  The synthesis of peptides which possess a high affinity for the somatostatin receptor and contain a chelator for the radionuclide technetium-99m is described. The target compounds were designed such that they would form stable, oxotechnetium(V) chelate complexes in which the site of metal coordination was well defined and remote from the receptor-binding region. Oxorhenium(V) chelate complexes of these peptides were prepared as nonradioactive surrogates for the technetium complexes. Peptide oxorhenium complexes and Tc-99m complexes eluted closely upon HPLC analysis. The receptor-binding affinities of both the free and rhenium-coordinated species were measured in vitro. The binding affinities of the free peptides (K-i's in the 0.25-10 nM range) compared favorably with [DTPA]octreotide (K-i = 1.6 nM), which, as the indium-lll complex, is already approved for somatostatin receptor (SSTR)-expressing tumor imaging in the United States and Europe. Furthermore, the rhenium-coordinated peptides had binding affinities which, in many cases, were higher than those of the corresponding free peptides, with several complexes having a K-i's of 0.1 nM. Some of the more potent SSTR-binding peptides were labeled with technetium-99m and assessed in an in vivo study with tumor-bearing rats. The Tc-99m-labeled peptides prepared in this study should be useful as SSTR-expressing tumor-imaging agents due to their high SSTR-binding affinities, ease of preparation, and, because they are low molecular weight peptides, expected pharmacokinetics characterized by rapid tracer excretion from the body resulting in high-contrast images.

  DOI：

  10.1021/jm950111m
• 作为产物：
  描述：

  L-缬氨酸甲酯 在 哌啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.75h， 生成 (S)-methyl 2-((S)-2-amino-6-((tert-butoxycarbonyl)amino)hexanamido)-3-methylbutanoate
  参考文献：
  名称：

  Enzymatic Timing and Tailoring of Macrolactamization in Syringolin Biosynthesis

  摘要：

  The enzymatic activation of 3,4-dehydrolysine and subsequent formation of the 12-membered syringolin macrolactam were investigated. The timing of the desaturation was elucidated through the analysis of the initial adenylation domain of SylD. The SylD-TTE didomain was characterized and demonstrated to be the catalyst for formation of 12-membered macrocycles. When the SylD thioesterase domain was reacted with a family of acyclic CoA both natural and unnatural macrocycles were generated.

  DOI：

  10.1021/ol2016687

文献信息

• PROCESS FOR PREPARING VAPREOTIDE
  申请人：Palle Acharyulu Venkata Raghavendra

  公开号：US20070111930A1

  公开（公告）日：2007-05-17

  A solution phase process for preparing vapreotide, having the formula:

  制备vapreotide的溶液相过程，其化学式为：
• Selective Conversion of<i>N</i>-Trichloroethoxycarbonyl (Troc) Groupsinto<i>N</i>-Acetyl Groups in thePresence of<i>N</i>-<i>tert</i>-Butoxycarbonyl(Boc) Protecting Groups
  作者：Richard R. Schmidt、Xiangming Zhu

  DOI：10.1055/s-2003-39405

  日期：——

  Deprotection of N-trichloroethoxycarbonyl (Troc) groups with zinc in acetic anhydride cleaves also N-tert-butoxycarbonyl (Boc) groups, thus liberating the amino groups, which are immediately N-acetylated. When this reaction is performed in the presence of triethylamine only Troc groups are selectively cleaved as demonstrated for several examples.

  用锌在乙酸酐中对 N-三氯乙氧羰基（Troc）进行脱保护反应，也会裂解 N-叔丁氧羰基（Boc），从而释放出氨基，氨基会立即被 N-乙酰化。在有三乙胺存在的情况下进行该反应时，只有 Troc 基团会被选择性地裂解，这一点已在多个实例中得到证实。