benzyl (6S,9S,12S)-6-isobutyl-12-isopropyl-9-(2-methoxy-2-oxoethyl)-2,2-dimethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oate | 1292797-89-7

• 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: benzyl (6S,9S,12S)-6-isobutyl-12-isopropyl-9-(2-methoxy-2-oxoethyl)-2,2-dimethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oate
• CAS: 1292797-89-7
• 化学式: C₂₈H₄₃N₃O₈
• 分子量: 549.665
• InChiKey: LLOCAALWWCXMJL-FUDKSRODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  39.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  149.13
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  benzyl (6S,9S,12S)-6-isobutyl-12-isopropyl-9-(2-methoxy-2-oxoethyl)-2,2-dimethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oate 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 methyl (S)-4-(((S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl)amino)-3-((S)-2-(2-(4-(3-(2,6-dimethylphenyl)ureido)phenyl)acetamido)-4-methylpentanamido)-4-oxobutanoate
  参考文献：
  名称：

  LDV peptidomimetics equipped with biotinylated spacer-arms: Synthesis and biological evaluation on CCRF-CEM cell line

  摘要：

  The tripeptide Leu-Asp-Val (LDV) is known to bind alpha(4)beta(1) integrin in leukemia cells. Here we have synthesized a LDV peptidomimetic equipped with a biotin-conjugated spacer-arm. Compound 9 acts as an inhibitor of the alpha(4)beta(1) integrin in an adhesion assay using fluorescently labeled, alpha(4)beta(1) integrin-expressing leukemia CCRF-CEM cells. Furthermore, when bound to neutravidin-coated plates, compound 9 could capture CCRF-CEM cells. Such biotin-conjugated LDV peptidomimetic may thus represent a novel tool for biotechnological applications using avidin interaction for leukapheresis or leukemia cell targeting. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.078
• 作为产物：
  描述：

  L-缬氨酸苄酯对甲苯磺酸盐 在 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 benzyl (6S,9S,12S)-6-isobutyl-12-isopropyl-9-(2-methoxy-2-oxoethyl)-2,2-dimethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oate
  参考文献：
  名称：

  LDV peptidomimetics equipped with biotinylated spacer-arms: Synthesis and biological evaluation on CCRF-CEM cell line

  摘要：

  The tripeptide Leu-Asp-Val (LDV) is known to bind alpha(4)beta(1) integrin in leukemia cells. Here we have synthesized a LDV peptidomimetic equipped with a biotin-conjugated spacer-arm. Compound 9 acts as an inhibitor of the alpha(4)beta(1) integrin in an adhesion assay using fluorescently labeled, alpha(4)beta(1) integrin-expressing leukemia CCRF-CEM cells. Furthermore, when bound to neutravidin-coated plates, compound 9 could capture CCRF-CEM cells. Such biotin-conjugated LDV peptidomimetic may thus represent a novel tool for biotechnological applications using avidin interaction for leukapheresis or leukemia cell targeting. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.078