H-N-Me-D-Leu-OBzl p-toluenesulfonic acid salt

• 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: H-N-Me-D-Leu-OBzl p-toluenesulfonic acid salt
• 英文别名: H-N-Me-D-Leu-OBzl*TosOH；H-N-Me-D-Leu-OBzl.TosOH；benzyl (2R)-4-methyl-2-(methylamino)pentanoate;4-methylbenzenesulfonic acid
• 化学式: C₇H₈O₃S*C₁₄H₂₁NO₂
• 分子量: 407.531
• InChiKey: HQAGSSPEDLUVSS-BTQNPOSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  H-N-Me-D-Leu-OBzl p-toluenesulfonic acid salt 、 BOC-L-亮氨酸 在 N,N-二异丙基乙胺 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 作用下， 以 四氢呋喃 为溶剂， 反应 6.08h， 以87%的产率得到Boc-L-Leu-N-Me-D-Leu-OBn
  参考文献：
  名称：

  线性亮氨酸同二肽的抗肿瘤活性及其潜在的作用机制。

  摘要：

  Galaxamide是一种稀有的环状同五肽，由从海水藻类Galaxaura silkosa分离出的三个亮氨酸和两个N-甲基亮氨酸组成。该化合物的强大抗肿瘤活性使其成为肿瘤治疗的有希望的候选者。然而，galaxamide的合成是一个复杂的过程，并且水溶性差。根据其特殊的化学组成，我们设计了一系列线性亮氨酸同系肽。在七个二肽衍生物中，具有末端保护基团和酰胺基团中氢的甲基取代基的五个化合物显示出对各种癌细胞的显着抑制作用。N-叔丁基-D-亮氨酸-N-甲基-D-亮氨酸苄基（A7）是由两个D-亮氨酸缩合而成的唯一立体异构体，具有最高的抗肿瘤活性。经A7处理的细胞表现出细胞周期停滞和典型的经历凋亡的细胞形态变化。Annexin-V阳性/碘化丙啶阴性细胞的数量也增加，表明诱导了早期凋亡。A7促进caspase-9和caspase-3的裂解，并增加细胞内Ca水平并降低线粒体膜电位。集体地，衍生自环状五肽的

  DOI：

  10.1097/cad.0000000000000615
• 作为产物：
  描述：

  N-叔丁氧羰基-N-甲基-D-亮氨酸 、 对甲苯磺酸 、 苯甲醇 以 甲苯 为溶剂， 反应 0.01h， 生成 H-N-Me-D-Leu-OBzl p-toluenesulfonic acid salt
  参考文献：
  名称：

  MW‐Enhanced High‐Speed Deprotection of Boc Group Usingp‐TsOH and Concommitant Formation ofN‐Me‐Amino Acid Benzyl Esterp‐TsOH Salts

  摘要：

  A high-speed, complete deprotection of Boc group from Boc amino acids and protected peptide esters employing p-TsOH in toluene under microwave irradiation is found to be complete in 30 s. The deprotection can be carried out in methanol and acetonitrile also. Under the present conditions, C-peptide benzyl esters and O-benzyl ethers have been found to be stable. This has permitted us to carry out the synthesis of [Leu] enkephalin employing the Boc/Bzl-group strategy. Further more, it has been found that both N-alpha-Fmoc and N-alpha-Z groups are completely stable. The present conditions can be extended for the concomitant removal of the Boc group and the formation of C-benzyl amino acid esters as well. This has been utilized for the synthesis of N-Me amino acid benzyl esters starting from Boc-N-Me amino acids in a single step.

  DOI：

  10.1081/scc-200063953

文献信息

• MW‐Enhanced High‐Speed Deprotection of Boc Group Using<i>p</i>‐TsOH and Concommitant Formation of<i>N</i>‐Me‐Amino Acid Benzyl Ester<i>p</i>‐TsOH Salts
  作者：Vommina V. Suresh Babu、Basanagoud S. Patil、Ganga‐Ramu Vasanthakumar

  DOI：10.1081/scc-200063953

  日期：2005.7

  A high-speed, complete deprotection of Boc group from Boc amino acids and protected peptide esters employing p-TsOH in toluene under microwave irradiation is found to be complete in 30 s. The deprotection can be carried out in methanol and acetonitrile also. Under the present conditions, C-peptide benzyl esters and O-benzyl ethers have been found to be stable. This has permitted us to carry out the synthesis of [Leu] enkephalin employing the Boc/Bzl-group strategy. Further more, it has been found that both N-alpha-Fmoc and N-alpha-Z groups are completely stable. The present conditions can be extended for the concomitant removal of the Boc group and the formation of C-benzyl amino acid esters as well. This has been utilized for the synthesis of N-Me amino acid benzyl esters starting from Boc-N-Me amino acids in a single step.
• Antineoplastic activity of linear leucine homodipeptides and their potential mechanisms of action
  作者：Yun Lei、Xiao-Xia Yang、Wei Guo、Fu-yong Zhang、Xiao-Jian Liao、Hui-Fu Yang、Shi-Hai Xu、Sheng Xiong

  DOI：10.1097/cad.0000000000000615

  日期：2018.7

  cleavage of caspase-9 and caspase-3, as well as increased intracellular Ca levels and decreased the mitochondrial membrane potential. Collectively, certain linear leucine dipeptides derived from cyclic pentapeptide are able to inhibit tumor cell proliferation through cell cycle arrest and apoptosis induction. The N-methyl group in the side chain and the D/L conformation of the amino-acid residue are critical

  Galaxamide是一种稀有的环状同五肽，由从海水藻类Galaxaura silkosa分离出的三个亮氨酸和两个N-甲基亮氨酸组成。该化合物的强大抗肿瘤活性使其成为肿瘤治疗的有希望的候选者。然而，galaxamide的合成是一个复杂的过程，并且水溶性差。根据其特殊的化学组成，我们设计了一系列线性亮氨酸同系肽。在七个二肽衍生物中，具有末端保护基团和酰胺基团中氢的甲基取代基的五个化合物显示出对各种癌细胞的显着抑制作用。N-叔丁基-D-亮氨酸-N-甲基-D-亮氨酸苄基（A7）是由两个D-亮氨酸缩合而成的唯一立体异构体，具有最高的抗肿瘤活性。经A7处理的细胞表现出细胞周期停滞和典型的经历凋亡的细胞形态变化。Annexin-V阳性/碘化丙啶阴性细胞的数量也增加，表明诱导了早期凋亡。A7促进caspase-9和caspase-3的裂解，并增加细胞内Ca水平并降低线粒体膜电位。集体地，衍生自环状五肽的