N-Fmoc-Gly-Gly-OBn | 150562-93-9

• 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: N-Fmoc-Gly-Gly-OBn
• 英文别名: (Fmoc)Gly-Gly(OBn)；benzyl 2-[[2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]amino]acetate
• CAS: 150562-93-9
• 化学式: C₂₆H₂₄N₂O₅
• 分子量: 444.487
• InChiKey: RCCCXDHTZYCVMN-UHFFFAOYSA-N

物化性质

• 沸点：
  680.5±45.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-Fmoc-Gly-Gly-OBn 在 potassium fluoride 、 18-冠醚-6 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以70%的产率得到glycylglycine benzyl ester
  参考文献：
  名称：

  Selective Removal of Fluorenylmethoxycarbonyl (FMOC) Groups Under Mild Conditions

  摘要：

  N-Fluorenylmethoxycarbonyl groups may be removed by potassium fluoride/18-crown-6 in the presence of methyl, ethyl, tert-butyl, benzyl, and p-methoxybenzyl esters.

  DOI：

  10.1080/00397919408013818
• 作为产物：
  描述：

  (9H-fluoren-9-yl)methyl [2-(6-methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl)allyl]carbamate 在 1,3-二氯-5,5-二甲基海因 、 臭氧 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 48.08h， 生成 N-Fmoc-Gly-Gly-OBn
  参考文献：
  名称：

  通过烯基硼酸酯的臭氧分解合成酰基硼：对映体富集的氨基酸酰基硼酸酯的制备

  摘要：

  在（o）区：通过对烯基MIDA硼酸酯进行臭氧分解来制备高度官能化的酰基酮。使用这种方法可以实现包括对映体纯的丙氨酸型酰基酮在内的α-氨基酰基酮的首次合成。该产品对于酰基三氟硼酸钾连接蛋白与蛋白的结合是必不可少的。使用α-氨基酰基酮的寡肽合成是在稀的水性介质中进行的，丙氨酸型酰基酮在连接条件下构型稳定。

  DOI：

  10.1002/anie.201707933

文献信息

• Synthesis of thioamides from thiocarboxylic acids using phosphonium-type condensing reagents
  作者：Ayaka Suzuki、Kazunori Takagi、Kazuki Sato、Takeshi Wada

  DOI：10.1016/j.tetlet.2021.153179

  日期：2021.7

  The synthesis of thioamides via the condensation reaction of thiocarboxylic acids with amines is described. Using 3-cyano-1,2,4-triazole as a favorable nucleophilic catalyst and 3-cyano-1,2,4-triazol-1-yl-tris(pyrrolidine-1-yl)phosphonium hexafluorophosphate (PyCTP) as a new phosphonium-type condensing reagent, thioamides are obtained selectively over amides, which can be attributed to the hardness

  描述了通过硫代羧酸与胺的缩合反应合成硫代酰胺。使用 3-氰基-1,2,4-三唑作为有利的亲核催化剂和 3-氰基-1,2,4-三唑-1-基-三（吡咯烷-1-基）六氟磷酸鏻（PyCTP）作为新的鏻型缩合剂，硫代酰胺比酰胺选择性地获得，这可归因于缩合剂磷中心的硬度。
• How Selective Threading of Amides through Macrocylic Lactam Wheels Leads to Rotaxane Synthesis
  作者：Christian Seel、Amir H. Parham、Oliver Safarowsky、Gosia M. Hübner、Fritz Vögtle

  DOI：10.1021/jo990042+

  日期：1999.9.1
• [EN] NOVEL STEROID PAYLOADS, STEROID LINKERS, ADCs CONTAINING AND USE THEREOF<br/>[FR] NOUVELLE CHARGE UTILE DE STÉROÏDE, LIEURS DE STÉROÏDES, CAM LES CONTENANT ET UTILISATION ASSOCIÉE
  申请人：[en]IMMUNEXT, INC.

  公开号：WO2022150637A1

  公开（公告）日：2022-07-14

  The invention provides novel glucocorticosteroids, glucocorticosteroid-linkers and antibody drug conjugates (ADC's) comprising an antibody or antibody fragment which binds to an antigen expressed on immune cells, optionally an antigen expressed on human immune cells. In some instances the ADCs comprise an anti-human VISTA (V-region Immunoglobulin-containing Suppressor of T cell Activation(1)) antibody or anti-VISTA antigen-binding antibody fragment which binds to VISTA expressing cells at physiologic pH having a short serum half-life (≈ 24-72 or 24-48 or 12-24 hours or less in a human VISTA knock-in rodent or ((≈ 1-3.5 days or less in a human or non-human primate). In some instances these ADCs have a rapid onset of action and are potent for prolonged duration as they are very effectively internalized by immune cells in large amounts where they are cleaved releasing large amounts of active steroid payload. The invention also relates to the use of such ADCs and novel steroids for the treatment of autoimmune, allergic and inflammatory conditions. The invention further relates to methods for reducing the adverse side effects and/or enhancing the efficacy of glucocorticoid receptor agonists by using such ADCs to selectively deliver these anti-inflammatory agents to target immune cells, such as monocytes, neutrophils, B cells, T cells, Tregs, eosinophils, NK cells, macrophages, myeloid cells, et al., and particularly myeloid cells, thereby reducing potential toxicity to non-target cells.