Boc-threonyl-proline methyl ester | 94790-38-2

• 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: Boc-threonyl-proline methyl ester
• 英文别名: Boc-Thr-Pro-OCH3；Boc-Thr-Pro-OMe；N-Boc-L-Thr-L-Pro methyl ester；N-Boc-Thr-Pro-OMe；methyl (2S)-1-[(2S,3R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]pyrrolidine-2-carboxylate
• CAS: 94790-38-2
• 化学式: C₁₅H₂₆N₂O₆
• 分子量: 330.381
• InChiKey: TYGNJVCJBVWXRD-VWYCJHECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-threonyl-proline methyl ester 在 二乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 Nδ-Boc-Orn(Nα-6-octyloxy-2-naphthoyl)-Thr-Pro-OMe
  参考文献：
  名称：

  Total synthesis and structure–activity relationships of caspofungin-like macrocyclic antifungal lipopeptides

  摘要：

  The echinocandins represent a well-known class of macrocyclic antifungal lipopeptides that can be used for treatment of invasive fungal infections. Due to their complex chemical structures and synthetic difficulties, the structure activity relationships (SARs) of them are still limited. A total synthetic approach was developed to synthesize structurally diverse caspofungin-like antifungal cyclic lipopeptides, allowing for systemically investigating their SARs. Most of the designed cyclic lipopeptides showed potent antifungal activities with broad spectrum. In particular, several compounds (e.g., 30a, 30e-h, 31a-d, 32c, and 33a,b) were more active in vitro against Candida albicans or Aspergillus fumigatus than caspofungin. The findings in this work indicated that the 'left' tripeptide segment of cyclic lipopeptide scaffold might be suitable for a hydrophilic structural motif, whereas the 'right' lipotripeptide segment was preferred as a hydrophobic core. The alkoxy-naphthoyl was found to be optimal side chain and alkyl length could affect the SARs of alkoxy-aroyl side chains. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.015
• 作为产物：
  描述：

  L-脯氨酸 在 氯化亚砜 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 Boc-threonyl-proline methyl ester
  参考文献：
  名称：

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

  摘要：

  DOI：

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

• <i>O</i>-Benzotriazolyl-<i>N</i>,<i>N</i>,<i>N</i>′,<i>N</i>′-tetramethyluronium Hexafluorophosphate as Coupling Reagent for the Synthesis of Peptides of Biological Interest
  作者：Vassilis Dourtoglou、Bernard Gross、Vassiliki Lambropoulou、Christine Zioudrou

  DOI：10.1055/s-1984-30895

  日期：——
• An efficient green synthesis of proline-based cyclic dipeptides under water-mediated catalyst-free conditions
  作者：Habeebullah Thajudeen、Kyungseok Park、Surk-Sik Moon、In Seok Hong

  DOI：10.1016/j.tetlet.2009.12.134

  日期：2010.3

  L-Proline-based cyclic dipeptides were synthesized from N-Boc-protected dipeptide methyl esters under catalyst-free condition using water as a solvent. One-pot deprotection and cyclization have been used is the key steps, providing an efficient and environmentally friendly approach. Clean reaction conditions, easy isolation, and good yields of cyclic dipeptides are the salient features of the proposed methodology (C) 2010 Elsevier Ltd All rights reserved.
• 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.