glycine allyl ester hydro-p-toluenesulfonate | 88223-98-7

• 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: glycine allyl ester hydro-p-toluenesulfonate
• 英文别名: H-Gly-OAll tosylate；p-toluenesulfonic acid salt of glycine allyl ester；glycine allyl ester hydrotosylate；H-Gly-OAll*pTosOH；allyl glycinate p-toluenesulfonate salt；allyl glycinate PTSA salt；allyl glycinate tosylate；4-Methylbenzenesulfonate;(2-oxo-2-prop-2-enoxyethyl)azanium；4-methylbenzenesulfonate;(2-oxo-2-prop-2-enoxyethyl)azanium
• CAS: 88223-98-7
• 化学式: C₅H₉NO₂*C₇H₈O₃S
• 分子量: 287.337
• InChiKey: WXSDKDUXXKHGJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-L-蛋氨酸 、 glycine allyl ester hydro-p-toluenesulfonate 在 1-羟基苯并三唑 、 达卡巴嗪 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以81%的产率得到N-tert-butyloxycarbonyl-L-methionyl-glycine allyl ester
  参考文献：
  名称：

  Synthesis of the palmitoylated and prenylated C-terminal lipopeptides of the human R- and N-Ras proteins

  摘要：

  For the study of biological phenomena influenced by the R- and N-Ras proteins, characteristic peptides which embody the correct lipid modifications of their parent proteins (palmitoyl thioesters, geranylgeranyl thioethers, and farnesyl thioethers), as well as analogues thereof, may serve as efficient tools. For the construction of such acid- and base labile peptide conjugates the allyl ester was developed as C-terminal protecting group. Allyl esters are cleaved selectively and in high yields from lipidated peptides by Pd(0)-mediated allyl transfer to accepting N- or C-nucleophiles like morpholine and N,N-dimethylbarbituric acid. This protecting group technique formed the key step in the synthesis of the characteristic S-palmitoylated and S-isoprenylated C-terminus of human R-Ras and human N-Ras proteins, as well as several analogues thereof. Deprotections are so mild that no undesired side reactions of the lipid conjugates are observed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00251-x
• 作为产物：
  描述：

  对甲苯磺酸 、 烯丙醇 、 聚甘氨酸 以 苯 为溶剂， 以84%的产率得到glycine allyl ester hydro-p-toluenesulfonate
  参考文献：
  名称：

  Waldmann, Herbert; Kunz, Horst, Liebigs Annalen der Chemie, 1983, # 10, p. 1712 - 1725

  摘要：

  DOI：

文献信息

• Synthesis of Functional <i>Ras</i> Lipoproteins and Fluorescent Derivatives
  作者：Karsten Kuhn、David J. Owen、Benjamin Bader、Alfred Wittinghofer、Jürgen Kuhlmann、Herbert Waldmann

  DOI：10.1021/ja002723o

  日期：2001.2.1

  protein. Furthermore, a preliminary study on the biological activity of the natural Ras protein derivative (containing the normal farnesyl and palmitoyl lipid residues) has shown full biological activity. This result highlights the usefulness of these compounds as invaluable tools for the study of Ras signal transduction processes and the plasma membrane localization of the Ras proteins.

  对于生物信号转导的研究，获得正确脂化的蛋白质至关重要。此外，获得包含正确蛋白质结构但可能额外携带不同脂质基团或标记（即荧光标签）的生物缀合物，通过这些标记可以在生物系统中追踪蛋白质，可以提供宝贵的试剂。我们在此报告一系列修饰 Ras 蛋白合成技术的发展。这些经过修饰的 Ras 蛋白携带许多不同的天然和非天然脂质残基，并且该过程还扩展为还提供了获得许多荧光标记衍生物的途径。马来酰亚胺基团提供了以特定和有效方式将化学合成的脂肽分子连接到截短形式的 H-Ras 蛋白的关键。此外，对天然 Ras 蛋白衍生物（含有正常法呢基和棕榈酰脂质残基）的生物活性的初步研究已显示出完整的生物活性。这一结果突出了这些化合物作为研究 Ras 信号转导过程和 Ras 蛋白的质膜定位的宝贵工具的有用性。
• A Novel Synthesis of Oligonucleotide–Peptide Conjugates with a Base-Labile Phosphate Linker between the Two Components According to the Allyl-Protected Phosphoramidite Strategy
  作者：Akira Sakakura、Yoshihiro Hayakawa

  DOI：10.1016/s0040-4020(00)00376-8

  日期：2000.6

  the hydroxyl of a serine or threonine residue of a peptide by a phosphodiester bond. This synthesis utilizes the phosphoramidite method with allyl for the phosphate linkages and the C-terminal of the peptide and allyloxycarbonyl for the nucleoside bases and the N-terminal of the peptide. In this synthesis, the removal of the allylic protecting groups and the detachment of the products was achieved under

  已经完成了对碱基不稳定的核苷酸-肽结合物的有效合成，其中两个组分通过磷酸二酯键直接连接在核苷酸的末端羟基和肽的丝氨酸或苏氨酸残基的羟基之间。该合成利用亚磷酰胺方法，其中烯丙基用于肽的磷酸键和C-末端，烯丙氧基羰基用于肽的核苷碱基和N-末端。在该合成中，在非碱性或温和的碱性条件下实现了烯丙基保护基的去除和产物的分离，从而使不稳定的磷酸酯连接基不引起明显的分解，因此以高纯度获得了目标缀合物。高产。
• Sequentially Photocleavable Protecting Groups in Solid-Phase Synthesis
  作者：Martin Kessler、Ralf Glatthar、Bernd Giese、Christian G. Bochet

  DOI：10.1021/ol027454g

  日期：2003.4.1

  [reaction: see text] A sequential solid-phase peptide synthesis was developed using both photolabile linker and protecting groups. The chromatic sequential lability between a tert-butyl ketone-derived linker (sensitive to irradiation at 305 nm) and a nitroveratryloxycarbonyl (NVOC) group (sensitive at 360 nm) was exploited to prepare Leu-Enkephalin in a 55% overall yield. This new strategy allows the

  [反应：见正文]使用光不稳定的连接基和保护基团开发了顺序的固相肽合成方法。利用叔丁基酮衍生的连接基（对305 nm的辐射敏感）和硝基过碳酰氧羰基（NVOC）基团（对360 nm敏感）之间的色序不稳定性来制备亮氨酸-脑啡肽，总产率为55％。通过避免使用常见的脱保护试剂（例如三氟乙酸或哌啶），该新策略允许在基本中性的介质中制备肽。
• Synthesis of glycopeptides from the carbohydrate-protein linkage region of proteoglycans
  作者：Sandrine Rio、Jean-Marie Beau、Jean-Claude Jacquinet

  DOI：10.1016/0008-6215(91)89043-f

  日期：1991.10

  non-glycosylated dipeptide segments, and coupling using the mixed-anhydride procedure allowed the construction in high yield of partially or fully glycosylated oligopeptides from the carbohydrate-protein linkage region of proteoglycan.

  将2,3,4,6-四-O-苯甲酰基-α-D-半乳糖核糖基三氯乙酰亚胺酸酯与苄基2,3-O-异亚丙基-β-D-吡喃吡喃糖苷缩合得到相应的β-（1 ---- 4 ）-连接的二糖衍生物，将其转化为2,3-二-O-苯甲酰基-4-O-（2,3,4,6-四-O-苯甲酰基-β-D-吡喃半乳糖基）-α-D-木吡喃糖基三氯乙酰亚氨酸。该糖基供体与一组选择性的C，N-保护的L-丝氨酸-甘氨酸二肽单元缩合。在糖基化或非糖基化二肽段的C末端或N末端进行选择性解封，并使用混合酸酐法进行偶联，可以从蛋白聚糖的碳水化合物-蛋白质连接区高产率构建部分或完全糖基化的寡肽。
• [EN] BIVALENT NUCLEIC ACID LIGANDS AND USES THEREFOR<br/>[FR] LIGANDS BIVALENTS D'ACIDES NUCLÉIQUES ET LEURS UTILISATIONS
  申请人：UNIV CARNEGIE MELLON

  公开号：WO2019126638A1

  公开（公告）日：2019-06-27

  Genetic recognition reagents comprising bivalent nucleobases are provided that bind two strands of nucleic acid, such as an expanded repeat sequence associated with an expanded repeat disease. In one example the expanded repeat disease is a polyQ disease, such as Huntington's disease. Methods of use of the reagents are provided, including a method of binding nucleic acid, such as an expanded repeat sequence associated with an expanded repeat disease, a method of identifying the presence of a nucleic acid comprising an expanded repeat, and a method of treating an expanded repeat disease are provided.

  提供了包含双价核碱基的基因识别试剂，能够结合两条核酸链，例如与扩增重复疾病相关的扩增重复序列。在一个示例中，这种扩增重复疾病是多聚Q疾病，如亨廷顿病。提供了试剂的使用方法，包括结合核酸的方法，例如与扩增重复疾病相关的扩增重复序列，识别包含扩增重复的核酸的方法，以及治疗扩增重复疾病的方法。