Phe-PheOAllyl | 212119-80-7

• 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: Phe-PheOAllyl
• 英文别名: prop-2-enyl (2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoate
• CAS: 212119-80-7
• 化学式: C₂₁H₂₄N₂O₃
• 分子量: 352.433
• InChiKey: WLSXNPKXBPMLAI-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 Phe-PheOAllyl 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 Boc-Phe-Phe-Oallyl
  参考文献：
  名称：

  用于反向固相肽合成的新型甲硅烷基接头

  摘要：

  用CO 2处理游离氨基酸酯，然后将其暴露于含氯硅烷的聚苯乙烯中，导致其附着在固体载体上。新形成的氨基甲酸酯甲硅烷基可用于在羧基末端构建多肽。使用CH 3 CN中的HF水溶液裂解（多肽）肽，生成游离胺形式的游离胺，将其分离为Boc衍生物。聚合物载体可以容易地回收。

  DOI：

  10.1016/s0040-4039(01)01093-0
• 作为产物：
  描述：

  L-phenylalanine allyl ester 生成 Phe-PheOAllyl
  参考文献：
  名称：

  用于反向固相肽合成的新型甲硅烷基接头

  摘要：

  用CO 2处理游离氨基酸酯，然后将其暴露于含氯硅烷的聚苯乙烯中，导致其附着在固体载体上。新形成的氨基甲酸酯甲硅烷基可用于在羧基末端构建多肽。使用CH 3 CN中的HF水溶液裂解（多肽）肽，生成游离胺形式的游离胺，将其分离为Boc衍生物。聚合物载体可以容易地回收。

  DOI：

  10.1016/s0040-4039(01)01093-0

文献信息

• New phenylfluorenyl based linkers for solid phase synthesis
  作者：Konrad H Bleicher、Christian Lutz、Yves Wüthrich

  DOI：10.1016/s0040-4039(00)01654-3

  日期：2000.11

  The synthesis of 9-(4-hydroxyphenyl)-9-H-fluoren-9-ol and 5-(4-(9-hydroxy-9H-fluoren-9-yl)-phenoxy)-pentanoic acid and their applications as new linkers for solid phase synthesis is reported. These supports show higher acid stability compared to standard trityl resins. Carboxylic acids and amines are immobilized and cleaved off after further modifications. TFA treatment releases the products in high

  9-（4-羟基苯基）-9-H-芴-9-醇和5-（4-（9-羟基-9H-芴-9-基）-苯氧基）-戊酸的合成及其新应用报道了用于固相合成的接头。与标准三苯甲基树脂相比，这些载体显示出更高的酸稳定性。羧酸和胺经过进一步修饰后被固定并裂解。TFA处理释放出的产品具有高收率和出色的纯度。
• Chemoenzymatic Synthesis of N-<i>Ras</i> Lipopeptides
  作者：Edgar Nägele、Michael Schelhaas、Norman Kuder、Herbert Waldmann

  DOI：10.1021/ja9805627

  日期：1998.7.1

  For the study of biological phenomena influenced by the plasma-membrane-bound Ras proteins and other lipidated proteins, characteristic peptides which embody the correct lipid modifications of their parent proteins (palmitoyl thioesters and farnesyl thioethers), as well as analogues thereof, may serve as suitable tools. For the construction of such acid- and base-labile peptide conjugates, the enzyme-labile p-acetoxybenzyloxycarbonyl (AcOZ) urethane blocking group was developed. The acetate moiety within the AcOZ group is easily saponified by treatment with acetyl esterase or lipase. After cleavage of the acetate group the resulting quinone methide spontaneously fragments, resulting in the liberation of the desired peptide or peptide conjugates. This enzymatic protecting group technique formed the key step in the synthesis of the characteristic S-palmitoylated and S-farnesylated C-terminus of the human N-Ras protein. Deprotections are so mild that no undesired side reactions of the lipid conjugates are observed (i.e., no hydrolysis or beta-elimination of the thioester and no acid-mediated attack on the double bonds of the farnesyl group). The combination of enzymatic protecting group techniques with classical chemical methods allowed access to various fluorescent-labeled and differently lipid-modified Rns lipopeptides. Their application in biological experiments enabeled the study of the structural requirements for the acylation of Ras sequence motifs in vivo and gave insight into the subcellular site at which these modifications occur. The results indicate that the plasma membrane is a major site of cellular S-acylation. This supports a mechanism for the selective subcellular localization of lipidated proteins, including the Rns proteins themselves, by kinetic targeting to the plasma membrane.
• Wagner; Heiner; Kunz, Synlett, 2000, # 12, p. 1753 - 1756
  作者：Wagner、Heiner、Kunz

  DOI：——

  日期：——
• Waldmann, Herbert; Naegele, Edgar, Angewandte Chemie, 1995, vol. 107, # 20, p. 2425 - 2428
  作者：Waldmann, Herbert、Naegele, Edgar

  DOI：——

  日期：——
• A new silyl linker for reverse-direction solid-phase peptide synthesis
  作者：Bruce H Lipshutz、Young-Jun Shin

  DOI：10.1016/s0040-4039(01)01093-0

  日期：2001.8

  Treatment of a free amino acid ester with CO2 followed by exposure to a chlorosilane-containing polystyrene results in its attachment to the solid support. The newly formed silyl carbamate can be employed to build polypeptides at the carboxyl terminus. Cleavage of the (poly)peptide using aqueous HF in CH3CN leads to its free amine form which is isolated as a Boc derivative. The polymer support can be

  用CO 2处理游离氨基酸酯，然后将其暴露于含氯硅烷的聚苯乙烯中，导致其附着在固体载体上。新形成的氨基甲酸酯甲硅烷基可用于在羧基末端构建多肽。使用CH 3 CN中的HF水溶液裂解（多肽）肽，生成游离胺形式的游离胺，将其分离为Boc衍生物。聚合物载体可以容易地回收。