N-[芴甲氧羰基]-3-[[(2-丙烯-1-基氧基)羰基]氨基]-D-丙氨酸 | 178924-05-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N-[芴甲氧羰基]-3-[[(2-丙烯-1-基氧基)羰基]氨基]-D-丙氨酸
• 中文别名: 芴甲氧羰基-3-[[(烯丙氧基)羰基]氨基]-D-丙氨酸
• 英文名称: Fmoc-Dap(Alloc)-OH
• 英文别名: Fmoc-D-Dap(Alloc)；Fmoc-D-Dpr(Alloc)-OH；N2-Fmoc-N3-Alloc-D-2,3-diaminopropanoic acid；(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((allyloxy)carbonyl)amino)propanoic acid；(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(prop-2-enoxycarbonylamino)propanoic acid
• CAS: 178924-05-5
• 化学式: C₂₂H₂₂N₂O₆
• 分子量: 410.426
• InChiKey: MPVGCCAXXFLGIU-LJQANCHMSA-N

物化性质

• 沸点：
  658.6±55.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 海关编码：
  2924299090
• 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：

  甲醇 、 N-[芴甲氧羰基]-3-[[(2-丙烯-1-基氧基)羰基]氨基]-D-丙氨酸 在 亚硝酸特丁酯 作用下， 反应 48.0h， 以66%的产率得到methyl (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3(((allyloxy)carbonyl)amino)propanoate
  参考文献：
  名称：

  亚硝酸叔丁酯促进的羧酸绿色酯化

  摘要：

  已经开发了TBN催化的羧酸绿色酯化反应，它具有多种底物和出色的官能团耐受性。机理研究证实，在系统中原位形成的亚硝酸是该转化的实际催化剂。

  DOI：

  10.1002/ejoc.202100326

文献信息

• The contribution of achiral residues in the laspartomycin family of calcium-dependent lipopeptide antibiotics
  作者：Thomas M. Wood、Kristine Bertheussen、Nathaniel I. Martin

  DOI：10.1039/c9ob02534k

  日期：——

  promising source of new antibiotic agents that are rich in structural and mechanistic diversity. Over forty unique CDAs have been identified to date and share a number of common features. Recent efforts in our group have provided new mechanistic and structural insights into the laspartomycin family of CDAs. We here describe investigations aimed at probing the role of the three glycine residues found in the

  抗菌素耐药性的日益增长的威胁已成为全球关注的问题。所谓的钙依赖性脂肽抗生素（CDA）已经成为具有丰富的结构和机制多样性的新型抗生素的有前途的来源。迄今为止，已经确定了40多种独特的CDA，它们具有许多共同的特征。我们小组的最新努力为Laspartomycin系列CDA提供了新的机制和结构见解。我们在此描述旨在调查在拉丝霉素肽大环化合物中发现的三个甘氨酸残基的作用的研究。为此，制备了包含非手性2-氨基异丁酸（AIB）以及1-或d-丙氨酸代替甘氨酸的拉丝霉素类似物，并评估了它们的抗菌活性。
• Solid-Phase Synthesis of Aza-Kahalalide F Analogues: (2<i>R</i>,3<i>R</i>)-2-Amino-3-azidobutanoic Acid as Precursor of the Aza-Threonine
  作者：Irene Izzo、Gerardo A. Acosta、Judit Tulla-Puche、Tommaso Cupido、Maria Jesus Martin-Lopez、Carmen Cuevas、Fernando Albericio

  DOI：10.1002/ejoc.200901345

  日期：2010.5

  The solid-phase synthesis of six novel analogues of Kahalalide F (KF), a natural product currently undergoing Phase II clinical trials, is reported. In all these compounds, amides were used as isosteres for the depsi bond. For two of these compounds, we performed an efficient synthesis of N-Fmoc-protected (2R,3R)-2-amino-3-azidobutanoic acid, precursor of the aza-threonine. This is the first example

  据报道，目前正在进行 II 期临床试验的天然产物 Kahalalide F (KF) 的六种新型类似物的固相合成。在所有这些化合物中，酰胺被用作 depsi 键的等排体。对于这些化合物中的两种，我们进行了 N-Fmoc 保护的 (2R,3R)-2-amino-3-azidobutanoic 酸（氮杂苏氨酸的前体）的有效合成。这是在固相中制备含氮杂-苏氨酸的肽中叠氮基团的固相还原的第一个例子。
• Orthogonal Chemistry for the Synthesis of Thiocoraline–Triostin Hybrids. Exploring their Structure–Activity Relationship
  作者：Judit Tulla-Puche、Sara Auriemma、Chiara Falciani、Fernando Albericio

  DOI：10.1021/jm4006093

  日期：2013.7.11

  The natural compounds triostin and thiocoraline are potent antitumor agents that act as DNA bisintercalators. From a pharmaceutical point of view, these compounds are highly attractive although they present a low pharmacokinetic profile, in part due to their low solubility. Synthetically, they represent a tour de force because no robust strategies have been developed to access a broad range of these bicyclic (depsi)peptides in a straightforward manner. Here we describe solid-phase strategies to synthesize new bisintercalators, such as thiocoraline triostin hybrids, as well is analogues bearing soluble tags. Orthogonal protection schemes (up to, five from: Fmoc, Boc Alloc, pNZ, o-NBS, and Troc), together with the right concourse of the coupling reagents (HOSu, HOBt, HOAt, Oxyma, EDC, DIPCDI, PyAOP, PyBOP, HATU, COMU), were crucial to establish the synthetic plan. In vitro studies and structure activity relationships have been shown trends in the structure activity relationship that Will facilitate the design of new bisintercalators.
• Structure −Activity Relationship Studies of Targeting Ligands against Breast Cancer Cells
  作者：Nianhuan Yao、Wenwu Xiao、Leah Meza、Harry Tseng、Mathida Chuck、Kit S. Lam

  DOI：10.1021/jm9012032

  日期：2009.11.12

  A series of LXY3 (1) analogues were designed and synthesized. Their binding affinity was demonstrated using MDA-MB-231 breast cancer cells adherence inhibition assay. Further structure-activity relationship was obtained. Analogue 29 was discovered to have 3.5-fold increase of the binding affinity. Fluorescent microscopy and in vivo and ex vivo imaging studies demonstrated that 29 is tin efficient in vivo targeting agent against alpha 3 integrin of MDA-MB-231 breast tumor xenograft implant.
• Green Esterification of Carboxylic Acids Promoted by <i>tert</i> ‐Butyl Nitrite
  作者：Yonggao Zheng、Yanwei Zhao、Suyan Tao、Xingxing Li、Xionglve Cheng、Gangzhong Jiang、Xiaobing Wan

  DOI：10.1002/ejoc.202100326

  日期：2021.5.14

  TBN‐catalyzed green esterification of carboxylic acids has been developed, which features a broad range of substrates and excellent functional groups tolerance. The mechanistic study confirmed that the nitrous acid formed in situ in the system is the actual catalyst for this transformation.

  已经开发了TBN催化的羧酸绿色酯化反应，它具有多种底物和出色的官能团耐受性。机理研究证实，在系统中原位形成的亚硝酸是该转化的实际催化剂。