N-tert-butoxycarbonyl-L-alanyl-D-glutamic acid α-benzyl ester | 50515-48-5

• 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: N-tert-butoxycarbonyl-L-alanyl-D-glutamic acid α-benzyl ester
• 英文别名: O¹-benzyl-N-(t-butoxycarbonyl-L-alanyl)-D-glutamic acid；α-benzyl tert-butyloxycarbonyl-L-alanyl-D-glutamate；(R)-5-(benzyloxy)-4-{(S)-2-[(tert-butoxycarbonyl)amino]propanamido}-5-oxopentanoic acid；Boc-Ala-D-Glu(ONHS)-OBn；Boc-L-Ala-α-D-Glu-OCH2-Ph；Boc-Ala-D-Glu-OBzl；(4R)-4-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-5-oxo-5-phenylmethoxypentanoic acid
• CAS: 50515-48-5
• 化学式: C₂₀H₂₈N₂O₇
• 分子量: 408.452
• InChiKey: AMFJVLAANHASBK-DZGCQCFKSA-N

物化性质

• 沸点：
  634.9±55.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-L-alanyl-D-glutamic acid α-benzyl ester 生成 (R)-2-((S)-2-Amino-propionylamino)-pentanedioic acid 1-benzyl ester
  参考文献：
  名称：

  BOUCHAUDON, JEAN;DUTRUC-ROSSET, GILLES;FARGE, DANIEL;JAMES, CLAUDE, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N, C. 695-701

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-1-benzyl 5-[2-(Trimethylsilyl)ethyl] 2-aminopentanedioate hydrochloride 在 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 N-tert-butoxycarbonyl-L-alanyl-D-glutamic acid α-benzyl ester
  参考文献：
  名称：

  细菌衍生肽聚糖交联片段的合成

  摘要：

  肽聚糖 (PG) 是细菌细胞壁的核心结构基序。从 PG 释放的片段是免疫系统的基本识别元件。然而，PG 的结构包含不同细菌物种之间的各种化学修饰。在这里，探讨了有机合成方法解决这种化学多样性的适用性，并使用溶液和固相方法介绍了带有生物相关氨基酸修饰和肽交联的交联 PG 片段的合成。

  DOI：

  10.1021/acs.joc.0c01852

文献信息

• Studies on structure-activity relationships of FK-156, an immunostimulating peptide, and related compounds. I. Synthesis of stereoisomeric analogues of FK-156.
  作者：HIDEKAZU TAKENO、SATOSHI OKADA、KEIJI HEMMI、MATSUHIKO ARATANI、YOSHIHIKO KITAURA、MASASHI HASHIMOTO

  DOI：10.1248/cpb.32.2925

  日期：——

  Five stereoisomeric analogues, 2-6, of FK-156 (1), an immunostimulating microbial metabolite, have been synthesized and screened for immunostimulating activity. The results indicate that the D-configuration of glutamic acid and L-configuration of diaminopimelic acid at the site combining with other amino acids are essential, while the configurations of lactic acid and alanine are of little importance for the biological activity of the FK-156 series.

  我们合成了一种免疫刺激微生物代谢物 FK-156 (1) 的五种立体异构体类似物 2-6，并对其进行了免疫刺激活性筛选。结果表明，在与其他氨基酸结合的部位，谷氨酸的 D-构型和二氨基丙二酸的 L-构型是必不可少的，而乳酸和丙氨酸的构型对 FK-156 系列的生物活性并不重要。
• ——
  作者：

  DOI：——

  日期：——
• Synthesis of a Fragment of Bacterial Cell Wall
  作者：Dusan Hesek、Mijoon Lee、Ken-ichiro Morio、Shahriar Mobashery

  DOI：10.1021/jo035583k

  日期：2004.3.1

  Cell wall is indispensable for survival of bacteria. This large molecular "mesh" encases the entire cytoplasm of bacteria, and it is comprised of repeating backbone units of N-acetyl-glucosamine (NAG)-N-acetyl-muramic acid (NAM). A pentapeptide is attached to each of the lactyl units of the N-acetyl-muramic acid. The cell wall has both cross-linked and non-cross-linked components. In the present paper, we have devised a synthetic route for the preparation of a fragment of the cell wall comprised of a tetrasaccharide (NAG-NAM-NAG-NAM), along with the two appended peptides. We also report the syntheses of three glycosyl donors (compounds 5, 7, and 9) and three glycosyl acceptors (compounds 4, 6, and 8) based on the D-glucosamine structure as a building unit. The synthetic strategy that is disclosed is generally useful in construction of other natural products containing the D-glucosamine as a building block.
• Bouchaudon, Jean; Dutruc-Rosset, Gilles; Farge, Daniel, Journal of the Chemical Society. Perkin transactions I, 1989, p. 695 - 701
  作者：Bouchaudon, Jean、Dutruc-Rosset, Gilles、Farge, Daniel、James, Claude

  DOI：——

  日期：——
• Total synthesis of FK-156 isolated from a Streptomyces as an immunostimulating peptide: application of a novel copper chelate amino protection
  作者：Keiji Hemmi、Hidekazu Takeno、Satoshi Okada、Osamu Nakaguchi、Yoshihiko Kitaura、Masashi Hashimoto

  DOI：10.1021/ja00413a070

  日期：1981.11