N-[叔丁氧羰基]-N'-9H-氧杂蒽-9-基-D-谷氨酰胺 | 99092-88-3

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 谷氨酰胺类衍生物
• 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: N-[叔丁氧羰基]-N'-9H-氧杂蒽-9-基-D-谷氨酰胺
• 英文名称: Boc-D-Gln(Xan)-OH
• 英文别名: (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-5-(9H-xanthen-9-ylamino)pentanoic acid
• CAS: 99092-88-3
• 化学式: C₂₃H₂₆N₂O₆
• 分子量: 426.469
• InChiKey: HOIIDGIJEPOSLL-MRXNPFEDSA-N

物化性质

• 密度：
  1.30

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[叔丁氧羰基]-N'-9H-氧杂蒽-9-基-D-谷氨酰胺 在 4-二甲氨基吡啶 、 2,4,5,6-四(9H-咔唑-9-基)异酞腈 、 三氟乙酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 16.0h， 生成 tert-butyl (4-((9H-xanthen-9-yl)amino)-1-(dimethoxyphosphoryl)-4-oxobutyl)carbamate
  参考文献：
  名称：

  使用可见光光催化通过脱羧磷酸化轻松将 α-氨基酸转化为 α-氨基磷酸盐

  摘要：

  据报道，使用有机光氧化还原催化，α-氨基酸通过其氧化还原活性酯轻松转化为相应的 α-氨基膦酸酯。一种新型光催化磷酸化结合了自由基-极性交叉与Arbuzov型反应性，为α-氨基膦酸盐的生成提供了一种操作简单、高产率和通用的合成方法。

  DOI：

  10.1002/anie.202207063

文献信息

• An Entirely Solid Phase Peptide Synthesis-Based Strategy for Synthesis of Gelatinase Biosynthesis-Activating Pheromone (GBAP) Analogue Libraries: Investigating the Structure–Activity Relationships of the <i>Enterococcus faecalis</i> Quorum Sensing Signal
  作者：Dominic N. McBrayer、Brooke K. Gantman、Crissey D. Cameron、Yftah Tal-Gan

  DOI：10.1021/acs.orglett.7b01444

  日期：2017.6.16

  The development of an entirely solid-phase peptide synthesis (SPPS)-based synthesis of the quorum sensing signal gelatinase biosynthesis-activating pheromone (GBAP) from Enterococcus faecalis is reported. The method was used to prepare three libraries of analogues to investigate the structure–activity relationships (SARs) of the GBAP signal. The SAR studies revealed new characteristics of the GBAP

  报告了粪肠球菌的群体感应信号明胶酶生物合成激活信息素（GBAP）的基于完全固相肽合成（SPPS）的合成技术的发展。该方法用于制备三个类似物库，以研究GBAP信号的结构-活性关系（SAR）。SAR研究揭示了GBAP信号的新特征，并揭示了迄今为止已知的粪肠球菌中最有效的群体感应激活剂。
• Structure−Activity Relationship Studies of Gonadotropin-Releasing Hormone Antagonists Containing <i>S</i>-Aryl/Alkyl Norcysteines and Their Oxidized Derivatives
  作者：Manoj P. Samant、Richard White、Doley J. Hong、Glenn Croston、P. Michael Conn、Jo Ann Janovick、Jean Rivier

  DOI：10.1021/jm0613931

  日期：2007.5.1

  A series of acyline analogues incorporating L- and D-isomers of S-arylated/alkylated norcysteines [Ncy(R), where R is 2-naphthyl, methyl, and isopropyl] at positions 1, 4, 7, and 10 were synthesized. Some of these analogues were mono- and dioxidized to sulfoxides and sulfones. All of the analogues of acyline were screened for the antagonism of the GnRH-induced response in a reporter gene assay in HEK-293 cells expressing the human GnRH receptor. Nine of the analogues (9, 11, 15, 16, 17, 19, 20 21, and 22) had antagonistic potency (IC50 < 2 nM) similar to that of acyline (IC50 = 0.52 nM) in this assay. Selected analogues (9, 11, 15, 16, 19, and 21) were tested in vitro for their antagonism at the rat GnRH-R in a reporter gene assay as well as in an in vivo intact male rat assay. Analogues 9 and 15 were the most potent in suppressing testosterone levels.