τ-L-histidino-D-alanine | 141949-35-1

• 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: τ-L-histidino-D-alanine
• 英文别名: L-histidino-D-alanine；L,D-HisAla
• CAS: 141949-35-1
• 化学式: C₉H₁₄N₄O₄
• 分子量: 242.235
• InChiKey: IZQGEZGZCIIKOP-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.75
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  144.46
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  dibenzyl Nα-tert-carbobenzyloxy-Nα'-benzyl-τ-L-histidino-D-alaninate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 48.0h， 以88%的产率得到τ-L-histidino-D-alanine
  参考文献：
  名称：

  Synthesis of Histidinoalanine: A Comparison of β-Lactone and Sulfamidate Electrophiles

  摘要：

  Previous syntheses of histidinoalanine (HAL) have led to mixtures of regioisomers and/or stereoisomers. For example, opening of N-Cbz-D-serine-beta-lactone (6) with Boc-L-His-OMe (5) gave a 2:1 mixture of tau- and pi-regioisomers. The sulfamidate 10, derived from N-benzyl-D-serine methyl ester (11), was reacted with Boc-L-His-OMe (5) to give the tau-HAL derivative 17 as a single isomer in 57% yield. A similarly prepared tau-HAL 19, bearing protecting groups that were all hydrogenolytically labile, led to the free bis-amino acid, tau-L-histidinyl-D-alanine (tau-4), as a salt-free standard for amino acid analysis.

  DOI：

  10.1021/jo200744d

文献信息

• Colony-wise Analysis of a <i>Theonella swinhoei</i> Marine Sponge with a Yellow Interior Permitted the Isolation of Theonellamide I
  作者：Kazuya Fukuhara、Kentaro Takada、Ryuichi Watanabe、Toshiyuki Suzuki、Shigeru Okada、Shigeki Matsunaga

  DOI：10.1021/acs.jnatprod.8b00591

  日期：2018.11.26

  There are several examples of marine organisms whose metabolic profiles differ among conspecifics inhabiting the same region. We have analyzed the metabolic profile of each colony of a Theonella swinhoei marine sponge with a yellow interior and noticed the patchy distribution of one metabolite. This compound was isolated and its structure was studied by a combination of spectrometric analyses and chemical

  有几个海洋生物的例子，它们的代谢谱在居住在同一地区的同种异体之间是不同的。我们分析了带有黄色内部的Theonella swinhoei海洋海绵每个菌落的代谢谱，并注意到一种代谢物的斑片状分布。分离出该化合物，并通过光谱分析和化学降解的组合研究了其结构，表明其为双环肽theonellamide类的同类物。以前，Theonellamides仅是由我们内部为白色的T. swinhoei而不是内部为黄色的T. swinhoei所分离。
• Synthesis of Histidinoalanine: A Comparison of β-Lactone and Sulfamidate Electrophiles
  作者：Carol M. Taylor、Samanthi Thabrew De Silva

  DOI：10.1021/jo200744d

  日期：2011.7.15

  Previous syntheses of histidinoalanine (HAL) have led to mixtures of regioisomers and/or stereoisomers. For example, opening of N-Cbz-D-serine-beta-lactone (6) with Boc-L-His-OMe (5) gave a 2:1 mixture of tau- and pi-regioisomers. The sulfamidate 10, derived from N-benzyl-D-serine methyl ester (11), was reacted with Boc-L-His-OMe (5) to give the tau-HAL derivative 17 as a single isomer in 57% yield. A similarly prepared tau-HAL 19, bearing protecting groups that were all hydrogenolytically labile, led to the free bis-amino acid, tau-L-histidinyl-D-alanine (tau-4), as a salt-free standard for amino acid analysis.