3-(2-(2-(4-((3-(prop-2-ynyloxy)-2,2-bis((prop-2-ynyloxy)methyl)propoxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)ethoxy)propanoic acid | 1271728-76-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2-(2-(4-((3-(prop-2-ynyloxy)-2,2-bis((prop-2-ynyloxy)methyl)propoxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)ethoxy)propanoic acid
• 英文别名: 3-[2-[2-[4-[[3-Prop-2-ynoxy-2,2-bis(prop-2-ynoxymethyl)propoxy]methyl]triazol-1-yl]ethoxy]ethoxy]propanoic acid；3-[2-[2-[4-[[3-prop-2-ynoxy-2,2-bis(prop-2-ynoxymethyl)propoxy]methyl]triazol-1-yl]ethoxy]ethoxy]propanoic acid
• CAS: 1271728-76-7
• 化学式: C₂₄H₃₃N₃O₈
• 分子量: 491.541
• InChiKey: QARBNFKUMRIGAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  35
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-(2-(2-(4-((3-(prop-2-ynyloxy)-2,2-bis((prop-2-ynyloxy)methyl)propoxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)ethoxy)propanoic acid 、 Fmoc-L-缬氨酸 、 Fmoc-L-亮氨酸 、 Fmoc-L-丙氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 Fmoc-O-叔丁基-L-苏氨酸 、 Fmoc-D-丙氨酸 、 Fmoc-L-色氨酸(Boc)-OH 、 芴甲氧羰酰基D-Β环己基丙氨酸 在 N-甲基咪唑 、 tentagel HMBA resin 、 苯甲基-2-磺酰三硝基三氮唑 、 哌嗪 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以90%的产率得到
  参考文献：
  名称：

  Synthesis of a Trimeric gp120 Epitope Mimic Conjugated to a T-Helper Peptide To Improve Antigenicity

  摘要：

  A fully synthetic trivalent mimotope of gp120 conjugated to pan allelic HLA DR binding epitope was prepared using solid-phase peptide synthesis and optimized copper-catalyzed azide-alkyne cycloaddition. The methodology efficiently provides chemically uniform heteromultimeric peptide constructs with enhanced binding, avidity, and specificity toward an established HIV-neutralizing human antibody, MAb b12. The versatile synthetic strategy serves as a powerful platform for the development of synthetic peptides as potential HIV-1 vaccine candidates.

  DOI：

  10.1021/ja1083915
• 作为产物：
  描述：

  tert-butyl 3-(2-(2-(4-((3-(prop-2-ynyloxy)-2,2-bis((prop-2-ynyloxy)methyl)propoxy)-methyl)-1H-1,2,3-triazol-1-yl)ethoxy)ethoxy)propanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以97%的产率得到3-(2-(2-(4-((3-(prop-2-ynyloxy)-2,2-bis((prop-2-ynyloxy)methyl)propoxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)ethoxy)propanoic acid
  参考文献：
  名称：

  Synthesis of a Trimeric gp120 Epitope Mimic Conjugated to a T-Helper Peptide To Improve Antigenicity

  摘要：

  A fully synthetic trivalent mimotope of gp120 conjugated to pan allelic HLA DR binding epitope was prepared using solid-phase peptide synthesis and optimized copper-catalyzed azide-alkyne cycloaddition. The methodology efficiently provides chemically uniform heteromultimeric peptide constructs with enhanced binding, avidity, and specificity toward an established HIV-neutralizing human antibody, MAb b12. The versatile synthetic strategy serves as a powerful platform for the development of synthetic peptides as potential HIV-1 vaccine candidates.

  DOI：

  10.1021/ja1083915

文献信息

• Synthesis of a Trimeric gp120 Epitope Mimic Conjugated to a T-Helper Peptide To Improve Antigenicity
  作者：Joan G. Schellinger、Lieza M. Danan-Leon、Jessica A. Hoch、Aemro Kassa、Indresh Srivastava、David Davis、Jacquelyn Gervay-Hague

  DOI：10.1021/ja1083915

  日期：2011.3.16

  A fully synthetic trivalent mimotope of gp120 conjugated to pan allelic HLA DR binding epitope was prepared using solid-phase peptide synthesis and optimized copper-catalyzed azide-alkyne cycloaddition. The methodology efficiently provides chemically uniform heteromultimeric peptide constructs with enhanced binding, avidity, and specificity toward an established HIV-neutralizing human antibody, MAb b12. The versatile synthetic strategy serves as a powerful platform for the development of synthetic peptides as potential HIV-1 vaccine candidates.