Thr-Pro-OMe | 76910-33-3

• 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: Thr-Pro-OMe
• 英文别名: methyl (2S)-1-[(2S,3R)-2-amino-3-hydroxybutanoyl]pyrrolidine-2-carboxylate
• CAS: 76910-33-3
• 化学式: C₁₀H₁₈N₂O₄
• 分子量: 230.264
• InChiKey: TYMOQWOYFBHEQO-CSMHCCOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Thr-Pro-OMe 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 二乙胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 122.0h， 生成 Nδ-Boc-Orn(Nα-6-heptyloxy-2-naphthoyl)-Thr-Pro-OMe
  参考文献：
  名称：

  Total synthesis and structure–activity relationships of new echinocandin-like antifungal cyclolipohexapeptides

  摘要：

  A series of new echinocandin-like cyclolipohexapeptides were designed and total synthesized via solution phase [3 + 3]-segment coupling strategy with an attempt to improve antifungal activity. The designed compounds showed potent antifungal activities with broad spectrum. In particular, 11 compounds (i.e. 28a-e, 28g, 28i-j, 29a, 29c and 29e) showed better in vitro antifungal activities against Candida albicans or Aspergillus fumigatus than caspofungin. Moreover, the synthesized compounds provided new SAR information for the echinocandins. The findings in this work suggested that the "left" tripeptide segment of cyclolipohexapeptide scaffold might be a hydrophilic structural motif, whereas the "right" lipopeptide segment was preferred as a hydrophobic core. The amino acid component of the cyclolipohexapeptide scaffold could significantly affect the SAR of the side chains. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.054
• 作为产物：
  描述：

  L-脯氨酸甲酯盐酸盐 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 26.33h， 生成 Thr-Pro-OMe
  参考文献：
  名称：

  Total synthesis and structure–activity relationships of new echinocandin-like antifungal cyclolipohexapeptides

  摘要：

  A series of new echinocandin-like cyclolipohexapeptides were designed and total synthesized via solution phase [3 + 3]-segment coupling strategy with an attempt to improve antifungal activity. The designed compounds showed potent antifungal activities with broad spectrum. In particular, 11 compounds (i.e. 28a-e, 28g, 28i-j, 29a, 29c and 29e) showed better in vitro antifungal activities against Candida albicans or Aspergillus fumigatus than caspofungin. Moreover, the synthesized compounds provided new SAR information for the echinocandins. The findings in this work suggested that the "left" tripeptide segment of cyclolipohexapeptide scaffold might be a hydrophilic structural motif, whereas the "right" lipopeptide segment was preferred as a hydrophobic core. The amino acid component of the cyclolipohexapeptide scaffold could significantly affect the SAR of the side chains. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.054

文献信息

• Synthetic and Cytotoxic and Antimicrobial Activity Studies on Annomuricatin B
  作者：Rajiv Dahiya、Monika Maheshwari、Rakesh Yadav

  DOI：10.1515/znb-2009-0215

  日期：2009.2.1

  Synthetic and Cytotoxic and Antimicrobial Activity Studies on Annomuricatin B

  合成和细胞毒性以及抗菌活性研究：关于Annomuricatin B

• Belagali; Himaja, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 4, p. 505 - 507
  作者：Belagali、Himaja

  DOI：——

  日期：——
• Total synthesis and structure–activity relationships of new echinocandin-like antifungal cyclolipohexapeptides
  作者：Jianzhong Yao、Hongming Liu、Ting Zhou、Hai Chen、Zhenyuan Miao、Chunquan Sheng、Wannian Zhang

  DOI：10.1016/j.ejmech.2012.01.054

  日期：2012.4

  A series of new echinocandin-like cyclolipohexapeptides were designed and total synthesized via solution phase [3 + 3]-segment coupling strategy with an attempt to improve antifungal activity. The designed compounds showed potent antifungal activities with broad spectrum. In particular, 11 compounds (i.e. 28a-e, 28g, 28i-j, 29a, 29c and 29e) showed better in vitro antifungal activities against Candida albicans or Aspergillus fumigatus than caspofungin. Moreover, the synthesized compounds provided new SAR information for the echinocandins. The findings in this work suggested that the "left" tripeptide segment of cyclolipohexapeptide scaffold might be a hydrophilic structural motif, whereas the "right" lipopeptide segment was preferred as a hydrophobic core. The amino acid component of the cyclolipohexapeptide scaffold could significantly affect the SAR of the side chains. (C) 2012 Elsevier Masson SAS. All rights reserved.