N,O-bis(trimethylsilyl)glycine | 7364-42-3

• 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: N,O-bis(trimethylsilyl)glycine
• 英文别名: N-trimethylsilanyl-glycine trimethylsilanyl ester；N-Trimethylsilyl-glycin-trimethylsilylester；Glycine, N-(trimethylsilyl)-, trimethylsilyl ester；trimethylsilyl 2-(trimethylsilylamino)acetate
• CAS: 7364-42-3
• 化学式: C₈H₂₁NO₂Si₂
• 分子量: 219.431
• InChiKey: SPAJELCPLFYXLX-UHFFFAOYSA-N

物化性质

• 沸点：
  97 °C(Press: 22 Torr)
• 密度：
  0.8975 g/cm3
• 保留指数：
  1098;1105;1105;1149;1141;1328

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,O-bis(trimethylsilyl)glycine 、 Fmoc-L-缬氨酸 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以80%的产率得到Fmoc-Val-Gly-OH
  参考文献：
  名称：

  Babu, Vommina V. Suresh; Kantharaju; Sudarshan, Naremaddepalli S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 8, p. 1880 - 1886

  摘要：

  DOI：
• 作为产物：
  描述：

  trimethyl(butyl-amino)silane 、 聚甘氨酸 生成 N,O-bis(trimethylsilyl)glycine
  参考文献：
  名称：

  Amplification of Growth Regulatory Genes in Intraductal Breast Cancer Is Associated with Higher Nuclear Grade but Not with the Progression to Invasiveness

  摘要：

  Ductal carcinoma in situ (DCIS), as an identifiable progenitor lesion of invasive breast cancer, represents a morphologically, biologically, and prognostically heterogeneous disease. It is not clear which molecular mechanisms are involved in progression to infiltrative growth. In this study, 83 DCIS classified according to the Van Nuys grading scheme were examined for amplification of growth regulatory genes that have been found to be amplified in invasive breast cancer (c-erbB2, topoisomerase II alpha, c-myc, and cyclinD1 genes). Exact quantification of gene amplification was enabled by a combination of laser microdissection of paraffin-embedded tissue with real-time PCR. In DCIS, gene amplifications of all tested genes were found. The most frequently amplified gene was c-erbB2 found in 21 of 83 (25%) cases. Amplification of the other genes under investigation was observed in 4% to 6% of cases, high-grade DCIS being predominantly affected. High-grade DCIS differed significantly from low- and intermediate-grade DCIS in frequency and level of c-erbB2 amplification. In addition, high-grade DCIS revealed an accumulation of genetic aberrations. Amplification status in pure in situ lesions did not differ from intraductal carcinoma with an infiltrative component, indicating that although associated with a higher nuclear grade gene amplification might not represent an independent prognostic marker of disease progression.

  DOI：

  10.1038/labinvest.3780265

文献信息

• 2-(4-Nitrophenyl)sulfonylethoxycarbonyl (Nsc) group as a base-labile α-amino protection for solid phase peptide synthesis
  作者：Vladimir V. Samukov、Aydar N. Sabirov、Pavel I. Pozdnyakov

  DOI：10.1016/0040-4039(94)80127-4

  日期：1994.10

  Base-lable 2-(4-nitrophenylsulfonyl)ethoxycarbonyl (Nsc) group is proposed for a temporary α-amino protection in the solid phase peptide synthesis. Nsc-Group is cleaved by organic bases in aprotic solvents under mild conditions similar to that used for Fmoc-group. Several Nα-Nsc amino acids are prepared and used in the solid phase synthesis of the fragment 307–318 of S-protein from bovine eye retina

  为了在固相肽合成中的临时α-氨基保护，提出了碱可支持的2-（4-硝基苯基磺酰基）乙氧基羰基（Nsc）基团。在与Fmoc-group相似的温和条件下，Nsc-Group在非质子传递溶剂中被有机碱裂解。制备了几种Nα-Nsc氨基酸，并将其用于固相合成牛眼视网膜S蛋白的307-318片段。
• A Facile Synthesis of Acylaminotetraoxysphirophosphoranes
  作者：Nan-Jing Zhang、Hai-Yan Lu、Xin Chen、Yu-Fen Zhao

  DOI：10.1055/s-1998-2050

  日期：1998.4

  Acylaminotetraoxyspirophosphorane 4, a new type of pentacoordinated phosphorus compound, was synthesized conveniently by the reaction of N,O-bis(trimethylsilyl)amino acid 2 with ethyl dichlorophosphinite, which was followed by the addition of phenanthrenequinone. This procedure provided an efficient methodology for the preparation of acylaminotetraoxysphirophosphorane and the ring formation of 1,3,2-azaoxaphospholane.

  新型五配位磷化合物酰胺四氧螺磷烷4通过N,O-双（三甲基硅基）氨基酸2与乙基二氯磷酸酯的反应方便合成，随后添加了菲噻啶醌。该方法为酰氨基四氧螺磷烷的制备及1,3,2-氮氧腈环的形成提供了高效的技术路线。
• Preparation, Isolation, and Characterization of <i>N</i>^α-Fmoc-peptide Isocyanates:  Solution Synthesis of Oligo-α-peptidyl Ureas
  作者：Vommina V. Sureshbabu、Basanagoud S. Patil、Rao Venkataramanarao

  DOI：10.1021/jo0611723

  日期：2006.9.1

  Nα-Fmoc-tripeptidyl urea ester and acids containing one each of peptide bond and urea bond. The divergent approach is extended to the synthesis of tetrapeptidyl ureas by the 2 + 2 strategy using bis-TMS−peptide acid as an amino component. To incorporate urea bonds in adjacent positions, Nα-Fmoc-peptidyl urea isocyanates 9a−d were prepared and employed in the synthesis of three tetrapeptidyl ureas 10a−b and 11

  所述Ñ α -Fmoc-肽的异氰酸酯3A - q，4A - Ç，和图5a - ç通过的Curtius重排制备Ñ α -Fmoc-肽酰基叠氮于甲苯下热，微波，和超声波的条件。所有Ñ α -Fmoc-低聚肽的异氰酸酯制成，分离稳定的结晶固体用71至94％的产率，并通过被完全表征1 H NMR，13 C NMR和质谱。其为寡-α肽脲的合成效用7A - ˚F和图8a -c通过发散耦合法得到证明。的耦合Ñ α -Fmoc-二肽的异氰酸酯与氨基酸酯或具有N，O二（三甲基硅基）氨基酸导致Ñ α -Fmoc-三肽基脲酯和含有各一个肽键和脲键的羧酸。发散的方法扩展到使用双-TMS-肽酸作为氨基成分的2 + 2策略合成四肽基脲。为了将脲键在相邻的位置，Ñ α -Fmoc肽尿素异氰酸9A - d被制备并在三个四肽脲的合成10a的- b和从N-末端开始连续包含一个肽键和两个脲键的11。然后该协议用于五个尿素的类似物的合成13
• Bortezomib Congeners Induce Apoptosis of Hepatocellular Carcinoma via CIP2A Inhibition
  作者：Duen-Ren Hou、Ann-Chi Huang、Chung-Wai Shiau、Chun-Yi Wang、Hui-Chuan Yu、Kuen-Feng Chen

  DOI：10.3390/molecules181215398

  日期：——

  CIP2A is an oncoprotein that upregulates p-Akt and promotes cancer cell proliferation and survival. The proteasome inhibitor bortezomib has been shown to reduce CIP2A and lead to cell apoptosis. Here; we modified the functional group of bortezomib to generate a series of novel compounds and conducted a structure–activity relationship (SAR) study. The results showed that compound 1 was able to repress CIP2A expression and cell apoptosis in the same manner as bortezomib, but with less potency in inhibition of proteasome activity. This finding provides a new direction for the design of CIP2A inhibitors.

  CIP2A 是一种上调 p-Akt 并促进癌细胞增殖和存活的肿瘤蛋白。蛋白酶体抑制剂硼替佐米已被证明能减少 CIP2A 并导致细胞凋亡。在此，我们对硼替佐米的官能团进行了修饰，生成了一系列新型化合物，并进行了结构-活性关系（SAR）研究。结果表明，化合物 1 能够以与硼替佐米相同的方式抑制 CIP2A 的表达和细胞凋亡，但对蛋白酶体活性的抑制作用较弱。这一发现为 CIP2A 抑制剂的设计提供了新的方向。
• New and efficient approach to the synthesis of pentacoordinate spirobicyclic phosphoranes
  作者：Hua Fu、Guang-Zhong Tu、Zhao-Long Li、Yu-Fen Zhao、Ri-Qing Zhang

  DOI：10.1039/a702813j

  日期：——

  Pentacoordinate spirobicyclic 2-phenoxy-1,3-phenylenedioxo-1,3,2-imino(alkyl)acetoxyphosphoranes are synthesized through a new and efficient method whereby phosphorus pentachloride is displaced stepwise by catechol, an N,O-bis(trimethylsilyl)amino acid and phenol (pathway A) or catechol, phenol and an N,O-bis(trimethylsilyl)amino acid (pathway B); this method has advantages of high yields, rapid reaction times and easy operation, which might provide a new route for the synthesis of other pentacoordinate phosphoranes.

  五配位螺双环 2-苯氧基-1,3-苯基二氧代-1,3,2-亚氨基(烷基)乙酰氧基磷烷是通过一种高效的新方法合成的，该方法通过儿茶酚、N,O-双(三甲基硅烷基)氨基酸和苯酚（途径 A）或儿茶酚、苯酚和 N,O-双(三甲基硅烷基)氨基酸（途径 B）逐步置换五氯化磷；该方法具有产率高、反应速度快、操作简便等优点，可为合成其他五配位膦类化合物提供新的途径。

表征谱图