N-(tert-butoxycarbonyl)-α-[2-(trimethylsilyl)ethoxy]-L-glutamic acid | 160450-14-6

• 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: N-(tert-butoxycarbonyl)-α-[2-(trimethylsilyl)ethoxy]-L-glutamic acid
• 英文别名: Boc-Glu-OTMSE；(4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-5-(2-trimethylsilylethoxy)pentanoic acid
• CAS: 160450-14-6
• 化学式: C₁₅H₂₉NO₆Si
• 分子量: 347.484
• InChiKey: HGJSRCKKQZGPKG-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-α-[2-(trimethylsilyl)ethoxy]-L-glutamic acid 在 对甲苯磺酸 、 7-甲基-1,5,7-三氮杂二环[4.4.0]癸-5-烯 作用下， 以 1,4-二氧六环 、 水 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 α-[2-(trimethylsilyl)ethoxy]-2-N-[2-(trimethylsilyl)ethoxycarbonyl]folic acid
  参考文献：
  名称：

  A step-wise synthetic approach is necessary to access γ-conjugates of folate: folate-conjugated prodigiosenes

  摘要：

  尽管有大量的文献描述了将叶酸与药效团反应，但这种方法无法有效地提供所需的共轭物的正确位置异构体。

  DOI：

  10.1039/c9ra01435g
• 作为产物：
  描述：

  N-叔丁氧羰基-L-谷氨酸 5-苄酯 在 乙醇 、 palladium 10% on activated carbon 、 氢气 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 生成 N-(tert-butoxycarbonyl)-α-[2-(trimethylsilyl)ethoxy]-L-glutamic acid
  参考文献：
  名称：

  用于靶向自组装紫杉醇基纳米粒子的叶酸功能化。

  摘要：

  报道了由以叶酸为靶向剂的缀合物和另一种以紫杉醇为活性剂的缀合物自组装的杂纳米颗粒。表征了含有不同百分比的叶酸缀合物的杂纳米颗粒，并确定了它们的生物活性。

  DOI：

  10.1039/d2ra06306a

文献信息

• Versatile Selective α-Carboxylic Acid Esterification of N-Protected Amino Acids and Peptides by Alcalase
  作者：Peter Quaedflieg、Timo Nuijens、Claudia Cusan、John Kruijtzer、Dirk Rijkers、Rob Liskamp

  DOI：10.1055/s-0028-1083362

  日期：——

  water, the industrial protease Alcalase allows selective synthesis of α-carboxylic acid methyl, ethyl, benzyl, allyl, 2-(trimethylsilyl)ethyl, and tert-butyl esters of amino acids and peptides under mild conditions in very high yields. The purified yields range from 72% to 92%. enzymes - amino acids - esterification - esters - protecting groups

  在连续去除水的条件下，工业蛋白酶Alcalase可以在温和条件下以很高的收率选择性合成氨基酸和肽的α-羧酸甲酯，乙酯，苄酯，烯丙基，2-（三甲基甲硅烷基）乙酯和叔丁酯。纯化的产率为72％至92％。 酶-氨基酸-酯化-酯-保护基
• Synthesis, characterization, and anticancer activity of folate γ-ferrocenyl conjugates
  作者：Diego L. Bertuzzi、Gabriel Perli、Carolyne B. Braga、Catia Ornelas

  DOI：10.1039/c9nj04954a

  日期：——

  Novel folate γ-ferrocene conjugates were synthesized through a regiospecific route, and showed selectivity and enhanced cytotoxicity against Frα-positive malignant cells.

  通过一个特定的路线合成了新型的叶酸γ-二茂铁共轭物，并且表现出对Frα阳性的恶性细胞的选择性和增强的细胞毒性。
• A step-wise synthetic approach is necessary to access γ-conjugates of folate: folate-conjugated prodigiosenes
  作者：Carlotta Figliola、Estelle Marchal、Brandon R. Groves、Alison Thompson

  DOI：10.1039/c9ra01435g

  日期：——

  Despite the vast literature that describes reacting folic acid with a pharmacophore, this route is ineffective in providing the correct regioisomer of the resulting conjugate.

  尽管有大量的文献描述了将叶酸与药效团反应，但这种方法无法有效地提供所需的共轭物的正确位置异构体。
• Cryptophane-Folate Biosensor for ¹²⁹Xe NMR
  作者：Najat S. Khan、Brittany A. Riggle、Garry K. Seward、Yubin Bai、Ivan J. Dmochowski

  DOI：10.1021/bc5005526

  日期：2015.1.21

  Folate-conjugated cryptophane was developed for targeting cryptophane to membrane-bound folate receptors that are overexpressed in many human cancers. The cryptophane biosensor was synthesized in 20 nonlinear steps, which included functionalization with folate recognition moiety, solubilizing peptide, and Cy3 fluorophore. Hyperpolarized Xe-129 NMR studies confirmed xenon binding to the folate-conjugated cryptophane. Cellular internalization of biosensor was monitored by confocal laser scanning microscopy and quantified by flow cytometry. Competitive blocking studies confirmed cryptophane endocytosis through a folate receptor-mediated pathway. Flow cytometry revealed 10-fold higher cellular internalization in KB cancer cells overexpressing folate receptors compared to HT-1080 cells with normal folate receptor expression. The biosensor was determined to be nontoxic in HT-1080 and KB cells by MTT assay at low micromolar concentrations typically used for hyperpolarized Xe-129 NMR experiments.
• Development of an Efficient Intermediate, α-[2-(Trimethylsilyl)ethoxy]-2-<i>N</i>- [2-(trimethylsilyl)ethoxycarbonyl]folic Acid, for the Synthesis of Folate (γ)-Conjugates, and Its Application to the Synthesis of Folate−Nucleoside Conjugates
  作者：Makoto Nomura、Satoshi Shuto、Akira Matsuda

  DOI：10.1021/jo000132a

  日期：2000.8.1