3-((R)-2,3-bis(palmitoyloxy)propylthio)-2-palmitamidopropanoic acid

• 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: 3-((R)-2,3-bis(palmitoyloxy)propylthio)-2-palmitamidopropanoic acid
• 英文别名: 3-[(2R)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-2-(hexadecanoylamino)propanoic acid
• 化学式: C₅₄H₁₀₃NO₇S
• 分子量: 910.48
• InChiKey: PZFZLRNAOHUQPH-UCNWKSROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.6
• 重原子数：
  63
• 可旋转键数：
  53
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-((R)-2,3-bis(palmitoyloxy)propylthio)-2-palmitamidopropanoic acid 在 copper(ll) sulfate pentahydrate 、 1-羟基苯并三唑 、 sodium ascorbate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 8.42h， 生成
  参考文献：
  名称：

  Design, synthesis and immunological evaluation of 1,2,3-triazole-tethered carbohydrate–Pam 3 Cys conjugates as TLR2 agonists

  摘要：

  Novel triazolyl Pam(3)Cys conjugates encompassing various carbohydrate entities have been synthesized by copper mediated azide-alkyne click chemistry protocol with a view to probe the SAR pertaining to their adjuvant activity in conjunction with OVA as antigen. The preliminary ex vivo cytokine profiling revealed optimal Th1 activation and the in vivo adjuvant studies of ribose derived hybrid (6e) revealed a marked improvement in the OVA specific antibody IgG response and Th1 cytokine expressions. The triazolyl Pam(3)Cys carbohydrate conjugates were found to be the hTLR2 agonists as revealed by their SEAP activity due to NFKB activation. The described protocol is the first successful attempt of the amalgamation of carbohydrate-Pam(3)Cys motifs tethered to a triazole linker as a peptide free adjuvant. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.06.070
• 作为产物：
  描述：

  (R)-3-(3-oxo-3-(2-oxo-2-phenylethoxy)-2-palmitamidopropylthio)propane-1,2-diyl dipalmitate 在 溶剂黄146 、 锌 作用下， 以90%的产率得到3-((R)-2,3-bis(palmitoyloxy)propylthio)-2-palmitamidopropanoic acid
  参考文献：
  名称：

  Design, synthesis and immunological evaluation of 1,2,3-triazole-tethered carbohydrate–Pam 3 Cys conjugates as TLR2 agonists

  摘要：

  Novel triazolyl Pam(3)Cys conjugates encompassing various carbohydrate entities have been synthesized by copper mediated azide-alkyne click chemistry protocol with a view to probe the SAR pertaining to their adjuvant activity in conjunction with OVA as antigen. The preliminary ex vivo cytokine profiling revealed optimal Th1 activation and the in vivo adjuvant studies of ribose derived hybrid (6e) revealed a marked improvement in the OVA specific antibody IgG response and Th1 cytokine expressions. The triazolyl Pam(3)Cys carbohydrate conjugates were found to be the hTLR2 agonists as revealed by their SEAP activity due to NFKB activation. The described protocol is the first successful attempt of the amalgamation of carbohydrate-Pam(3)Cys motifs tethered to a triazole linker as a peptide free adjuvant. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.06.070

文献信息

• Design, synthesis and immunological evaluation of 1,2,3-triazole-tethered carbohydrate–Pam 3 Cys conjugates as TLR2 agonists
  作者：Naresh Nalla、Preethi Pallavi、Bonam Srinivasa Reddy、Sreekanth Miryala、V. Naveen Kumar、Mohammed Mahboob、M. Sampath Kumar Halmuthur

  DOI：10.1016/j.bmc.2015.06.070

  日期：2015.9

  Novel triazolyl Pam(3)Cys conjugates encompassing various carbohydrate entities have been synthesized by copper mediated azide-alkyne click chemistry protocol with a view to probe the SAR pertaining to their adjuvant activity in conjunction with OVA as antigen. The preliminary ex vivo cytokine profiling revealed optimal Th1 activation and the in vivo adjuvant studies of ribose derived hybrid (6e) revealed a marked improvement in the OVA specific antibody IgG response and Th1 cytokine expressions. The triazolyl Pam(3)Cys carbohydrate conjugates were found to be the hTLR2 agonists as revealed by their SEAP activity due to NFKB activation. The described protocol is the first successful attempt of the amalgamation of carbohydrate-Pam(3)Cys motifs tethered to a triazole linker as a peptide free adjuvant. (C) 2015 Elsevier Ltd. All rights reserved.