FMOC-ALPHA-谷氨酸盐 | 292150-20-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 谷氨酸类衍生物
• 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
• 中文名称: FMOC-ALPHA-谷氨酸盐
• 中文别名: (4R)-5-氨基-4-[[芴甲氧羰基]氨基]-5-氧代戊酸；FMOC-α-谷氨酸盐；Fmoc-D-isoGln-OH
• 英文名称: N-Fmoc-D-isoglutamine
• 英文别名: Fmoc-D-isoGln；Fmoc-D-isoglutamine；Fmoc-D-iso-Gln-OH；Fmoc-D-isoGln-OH；Fmoc-D-iGln-OH；(4R)-5-amino-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxopentanoic acid
• CAS: 292150-20-0
• 化学式: C₂₀H₂₀N₂O₅
• 分子量: 368.389
• InChiKey: MZRFDZFXTSDMFA-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  对氯肉桂酸 、 Fmoc-L-丙氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 FMOC-ALPHA-谷氨酸盐 在 Rink amide resin 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 Nα-[4-chlorocinnamoyl-L-alanyl-D-isoglutaminyl]-L-lysine
  参考文献：
  名称：

  Conjugate (MTC-220) of Muramyl Dipeptide Analogue and Paclitaxel Prevents Both Tumor Growth and Metastasis in Mice

  摘要：

  1 (MTC-220), a conjugate of paclitaxel and a muramyl dipeptide analogue, has been synthesized as a novel agent of dual antitumor growth and metastasis activities. In vitro and in vivo tests show that 1 retains its ability to inhibit tumor growth. It is superior to paclitaxel in its ability to prevent tumor metastasis in Lewis lung carcinoma and 4T1-tumor-bearing mice. The present studies indicate that 1 suppresses myeloid derived suppressor cell accumulation in the spleen and bone marrow of tumor-bearing mice and also represses inflammatory cytokines in tumor tissue. These results demonstrated that 1 could be a potential therapeutic and preventive agent for cancer growth and metastasis.

  DOI：

  10.1021/jm101577z
• 作为产物：
  描述：

  D-谷氨酸 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 20.0~60.0 ℃ 、400.0 kPa 条件下， 反应 87.75h， 生成 FMOC-ALPHA-谷氨酸盐
  参考文献：
  名称：

  A Novel Immunostimulator, N²-[α-O-Benzyl-N-(acetylmuramyl)-l-alanyl-d- isoglutaminyl]-N⁶-trans-(m-nitrocinnamoyl)-l-lysine, and Its Adjuvancy on the Hepatitis B Surface Antigen

  摘要：

  N-2-[(alpha-O-Benzyl-N-(acetylmuramyl)-L-alanyl-D-isoglutaminyl)]-AT6-trans-(m-nitrocinnamoyl)-L-lysine (muramyl dipeptide C, or MDP-C) has been synthesized as a novel, nonspecific immunomodulator. The present study shows that MDP-C induces strong cytolytic activity by macrophages on P388 leukemia cells and cytotoxic activity by cytotoxic T lymphocytes (CTLs) on P815 mastocytoma cells. Our results also indicate that MDP-C is an effective stimulator for production of interleukin-2 and interleukin-12 by murine bone morrow derived dendritic cells (BMDCs) and production of interferon-gamma by CTLs. Additionally, MDP-C increases the expression levels of several surface molecules, including CD11c, MHC class I, and intercellular adhesion molecule-1 in BMDCs. Moreover, MDP-C remarkably enhances the immune system's responsiveness to hepatitis B surface antigen (HBsAg) in hepatitis B virus transgenic mice for both antibody production and specific HBsAg T-cell responses ex vivo. Our results indicate that MDP-C is an apyrogenic, nonallergenic, and low-toxicity immunostimulator with great potential for diagnostic, immunotherapeutic, and prophylactic applications in diseases such as hepatitis B and cancers.

  DOI：

  10.1021/jm0493313

文献信息

• Antagonizing NOD2 Signaling with Conjugates of Paclitaxel and Muramyl Dipeptide Derivatives Sensitizes Paclitaxel Therapy and Significantly Prevents Tumor Metastasis
  作者：Yi Dong、Suhua Wang、Chunting Wang、Zihua Li、Yao Ma、Gang Liu

  DOI：10.1021/acs.jmedchem.6b01704

  日期：2017.2.9

  A noncleavable paclitaxel (PTX) and N-acetylmuramyl-l-alanyl-d-isoglutamine (MDP) derivative conjugate, 22 (DY-16-43), and its analogues were prepared and characterized as antagonists of NOD2 signaling. This conjugate enhanced the antitumor and antimetastatic efficacy of PTX in Lewis lung carcinoma (LLC) tumor-bearing mice. This work first describes a molecular strategy that enables the sensitization

  制备了不可裂解的紫杉醇（PTX）和N-乙酰基村m - 1-丙氨酰基-d-异谷氨酰胺（MDP）衍生物共轭物22（DY-16-43），及其类似物，并被表征为NOD2信号转导的拮抗剂。该缀合物增强了PTX在Lewis肺癌（LLC）荷瘤小鼠中的抗肿瘤和抗转移功效。这项工作首先描述了一种分子策略，该策略能够通过拮抗NOD2炎症信号来增强化学疗法的反应，并建议将NOD2拮抗剂作为治疗非小细胞肺癌（NSCLC）的潜在辅助药物。
• The synthesis of diaminopimelic acid containing peptidoglycan fragments using metathesis cross coupling
  作者：Abhijit Roy Chowdhury、Geert-Jan Boons

  DOI：10.1016/j.tetlet.2005.01.062

  日期：2005.3

  protected diaminopimelic acid (DAP), a component of peptidoglycan of Gram-negative bacteria, was prepared by a metathesis cross coupling between properly protected allyl and vinyl glycine derivatives using Grubb’s second-generation catalyst followed by reduction of the double bond of the resulting compound. The DAP derivatives were used in the solution- and polymer-supported synthesis of biological active peptides

  正确保护的二氨基庚二酸（DAP）是革兰氏阴性细菌的肽聚糖的一种成分，它是通过使用第二代催化剂Grubb在适当保护的烯丙基和乙烯基甘氨酸衍生物之间进行易位交叉偶联，然后还原所得化合物的双键来制备的。DAP衍生物用于溶液和聚合物支持的生物活性肽合成中。
• Solid-phase synthesis of muramyl dipeptide (mdp) derivatives using a multipin method
  作者：Gang Liu、Shuo-De Zhang、Shu-Quan Xia、Zhen-Kai Ding

  DOI：10.1016/s0960-894x(00)00241-9

  日期：2000.6

  Solid-phase synthetic method of muramyl dipeptide derivatives is reported. A diverse library of muramyl dipeptides could be potentially synthesized by acylation, reductive alkylation, sulfonamide formation, urea formation, N-alkylation, amine addition, or component Ugi reactions based on this method for drug screening.

  报道了固相合成穆拉基二肽衍生物的方法。基于此药物筛选方法，可以通过酰化，还原烷基化，磺酰胺形成，尿素形成，N-烷基化，胺加成或组分Ugi反应潜在地合成多样的穆拉基二肽文库。
• CHEMICAL SYNTHESIS AND ANTI-TUMOR AND ANTI-METASTATIC EFFECTS OF DUAL FUNCTIONAL CONJUGATE
  申请人：Shenzhen Salubris Pharmaceuticals Co., Ltd.

  公开号：EP2612857B1

  公开（公告）日：2017-07-26
• US9085605B2
  申请人：——

  公开号：US9085605B2

  公开（公告）日：2015-07-21