O-propargyl-L-serine hydrochloride | 1379150-93-2

• 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: O-propargyl-L-serine hydrochloride
• 英文别名: O-propargyl serine；(2S)-2-amino-3-prop-2-ynoxypropanoic acid
• CAS: 1379150-93-2
• 化学式: C₆H₉NO₃
• 分子量: 143.142
• InChiKey: CBKWZMZSOKUORR-YFKPBYRVSA-N

物化性质

• 沸点：
  317.9±37.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-propargyl-L-serine hydrochloride 在 N-甲基吗啉 、 吡啶 、 O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate 、 氧气 、 copper(II) acetate monohydrate 、 碳酸氢钠 、 三乙胺 、 nickel dichloride 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Oxidative α,ω-diyne coupling as an approach towards novel peptidic macrocycles

  摘要：

  Glaser-Hay diyne偶联被证明是一种有效的环化方法，用于制备含有diyne的肽宏环。

  DOI：

  10.1039/c5ob01153a
• 作为产物：
  描述：

  (S)-2-[(tert-butoxycarbonyl)amino]-3-(prop-2-yn-1-yloxy)propanoic acid 在 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 0.17h， 以100%的产率得到O-propargyl-L-serine hydrochloride
  参考文献：
  名称：

  分层超分子凝胶：自组装的肽和照片控释通过主客体相互作用

  摘要：

  分层的超分子水凝胶是由Fmoc-RGDS四肽自组装而成的，显示出受主与客体相互作用的光控释放。从单个肽水凝胶中连续释放出多种有效载荷，包括囊泡。

  DOI：

  10.1039/c7cc07859e

文献信息

• Synthesis and Characterisation of Substrate-Based Peptides as Inhibitors of Histone Demethylase KDM4C
  作者：Simon D. Nielsen、Ulrike Leurs、Magnus Bergner、Silvia A. Barris、Kanchan Devkota、Kamilla Meyer,、Daniella Iaria、Jack McCaughan、Brian Lohse、Jesper L. Kristensen、Rasmus P. Clausen

  DOI：10.2174/0929866523666160613210831

  日期：2016.8.8

  The design and synthesis of modified pentapeptides based on a truncated version of the substrate for KDM4C, a histone lysine demethylase (KDM), and investigation of their inhibitory activity at KDM4C is reported. By modifying the lysine residue corresponding to lysine 9 at histone 3 (H3K9), three different series of peptides were designed and synthesized. One series contained N-acylated H3K9 and two series introduced triazoles in this position via click chemistry to enable facile variation of headgroups. The click reaction is compatible with free amino acids and this was performed on an azido containing deprotected pentapeptide demonstrating a highly facile and convergent synthetic strategy for making substrate-based inhibitors. One of the 14 peptides showed inhibitory activity at KDM4C demonstrating the need for an iron chelator in the pentapeptide series.

  本文报道了基于组蛋白赖氨酸去甲基酶KDM4C的底物截短版本的修饰五肽的设计与合成，并研究了它们对KDM4C的抑制活性。通过修饰对应于组蛋白3第9位赖氨酸(H3K9)的赖氨酸残基，设计并合成了三个不同系列的肽。其中一个系列包含N-酰化的H3K9，另外两个系列通过点击化学在此位置引入三唑以实现头部基团的便捷变化。点击反应与自由氨基酸兼容，这一反应在含有叠氮基的去保护五肽上进行，展示了一种高度便捷和集中的合成策略，用于制造基于底物的抑制剂。14个五肽中的一个显示出对KDM4C的抑制活性，这表明五肽系列中需要铁螯合剂。
• Macrocyclic compounds
  申请人：Ziylo Limited

  公开号：US10800747B2

  公开（公告）日：2020-10-13

  The present invention relates to macrocyclic compounds which are capable of selective binding to a target saccharide (e.g. glucose), making them particularly well suited for use in saccharide sensing applications. The present invention also relates to processes for the preparation of said compounds, to compositions and devices comprising them, and to their use in the detection of a target saccharide.

  本发明涉及能够选择性结合目标糖（如葡萄糖）的大环化合物，使其特别适合用于糖传感应用。本发明还涉及制备所述化合物的工艺、包含这些化合物的组合物和装置，以及它们在检测目标糖类中的用途。
• In Vitro Membrane Permeation Studies and in Vivo Antinociception of Glycosylated Dmt¹-DALDA Analogues
  作者：Steven Ballet、Cecilia Betti、Alexandre Novoa、Csaba Tömböly、Carsten Uhd Nielsen、Hans Christian Helms、Anna Lesniak、Patrycja Kleczkowska、Nga N. Chung、Andrzej W. Lipkowski、Birger Brodin、Dirk Tourwé、Peter W. Schiller

  DOI：10.1021/ml4004765

  日期：2014.4.10

  In this study the mu opioid receptor (MOR) ligands DALDA (Tyr-D-Arg-Phe-Lys-NH2) and Dmt(1)-DALDA (Dmt-D-Arg-Phe-Lys-NH2, Dmt = 2',6'-dimethyltyrosine) were glycosylated at the N- or C-terminus. Subsequently, the modified peptides were subjected to in vitro and in vivo evaluation. In contrast to the N-terminally modified peptide (3), all peptide analogues derivatized at the C-terminus (4-7) proved to possess high affinity and agonist potency at both MOR and DOR (delta opioid receptor). Results of the Caco-2 monolayer permeation, as well as in vitro blood-brain barrier model experiments, showed that, in the case of compound 4, the glycosylation only slightly diminished the lumen-to-blood and blood-to-lumen transport. Altogether, these experiments were indicative of transcellular transport but not active transport. In vivo assays demonstrated that the peptides were capable of (i) crossing the blood-brain barrier (BBB) and (ii) activating both the spinal ascending as well as the descending opioid pathways, as determined by the tail-flick and hot-plate assays, respectively. In contrast to the highly selective MOR agonist Dmt(1)-DALDA 1, compounds 4-7 are mixed MOR/DOR agonists, expected to produce reduced opioid-related side effects.
• MACROCYCLIC COMPOUNDS
  申请人：Ziylo Limited

  公开号：US20200399232A1

  公开（公告）日：2020-12-24

  The present invention relates to macrocyclic compounds which are capable of selective binding to a target saccharide (e.g. glucose), making them particularly well suited for use in saccharide sensing applications. The present invention also relates to processes for the preparation of said compounds, to compositions and devices comprising them, and to their use in the detection of a target saccharide.