(S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-aminopropanoic acid hydrochloride | 366009-04-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-aminopropanoic acid hydrochloride
• 英文别名: Fmoc-Dap-OH*HCl；(2S)-2-amino-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid hydrochloride；(2S)-2-amino-3-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid;hydrochloride
• CAS: 366009-04-3
• 化学式: C₁₈H₁₈N₂O₄*ClH
• 分子量: 362.813
• InChiKey: QQISDBYKQHASPJ-NTISSMGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  102
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4E)-反式环辛烯-琥珀酰亚胺酯 、 (S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-aminopropanoic acid hydrochloride 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以35 %的产率得到(2S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((((E)-cyclooct-4-en-1-yl)oxy)carbonyl)amino)propanoic acid
  参考文献：
  名称：

  A Bioorthogonal Dual Fluorogenic Probe for the Live‐Cell Monitoring of Nutrient Uptake by Mammalian Cells

  摘要：

  Cells rely heavily on the uptake of exogenous nutrients for survival, growth, and differentiation. Yet quantifying the uptake of small molecule nutrients at the single cell level is difficult. Here we present a new approach to studying the nutrient uptake in live single cells using Inverse Electron‐Demand Diels Alder (IEDDA) chemistry. We have modified carboxyfluorescein‐diacetate‐succinimidyl esters (CFSE)—a quenched fluorophore that can covalently react with proteins and is only turned on in the cytosol of a cell following esterase activity—with a tetrazine. This tetrazine serves as a second quencher for the pendant fluorophore. Upon reaction with nutrients modified with an electron‐rich or strained dienophile in an IEDDA reaction, this quenching group is destroyed, thereby enabling the probe to fluoresce. This has allowed us to monitor the uptake of a variety of dienophile‐containing nutrients in live primary immune cell populations using flow cytometry and live‐cell microscopy.

  DOI：

  10.1002/anie.202401733
• 作为产物：
  描述：

  Fmoc-Dap(Boc)-OH*HCl 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 (S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-aminopropanoic acid hydrochloride
  参考文献：
  名称：

  A Bioorthogonal Dual Fluorogenic Probe for the Live‐Cell Monitoring of Nutrient Uptake by Mammalian Cells

  摘要：

  Cells rely heavily on the uptake of exogenous nutrients for survival, growth, and differentiation. Yet quantifying the uptake of small molecule nutrients at the single cell level is difficult. Here we present a new approach to studying the nutrient uptake in live single cells using Inverse Electron‐Demand Diels Alder (IEDDA) chemistry. We have modified carboxyfluorescein‐diacetate‐succinimidyl esters (CFSE)—a quenched fluorophore that can covalently react with proteins and is only turned on in the cytosol of a cell following esterase activity—with a tetrazine. This tetrazine serves as a second quencher for the pendant fluorophore. Upon reaction with nutrients modified with an electron‐rich or strained dienophile in an IEDDA reaction, this quenching group is destroyed, thereby enabling the probe to fluoresce. This has allowed us to monitor the uptake of a variety of dienophile‐containing nutrients in live primary immune cell populations using flow cytometry and live‐cell microscopy.

  DOI：

  10.1002/anie.202401733

文献信息

• [EN] MACROCYCLIC PEPTIDES USEFUL AS IMMUNOMODULATORS<br/>[FR] PEPTIDES MACROCYCLIQUES UTILES COMME IMMUNOMOLDULATEURS
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2016077518A1

  公开（公告）日：2016-05-19

  The present disclosure provides compounds which are immunomodulators and thus are useful for the amelioration of various diseases, including cancer and infectious diseases.

  本公开提供了一些免疫调节剂化合物，因此对于改善各种疾病，包括癌症和传染病，具有用处。