(S)-methyl 2-(2-((tert-butoxycarbonyl)amino)acetamido)-3-(3,4-dihydroxyphenyl)propanoate | 1196734-96-9

• 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: (S)-methyl 2-(2-((tert-butoxycarbonyl)amino)acetamido)-3-(3,4-dihydroxyphenyl)propanoate
• 英文别名: Boc-Gly-DOPA-OMe；Boc-Gly-Tyr(3-OH)-OMe；methyl (2S)-3-(3,4-dihydroxyphenyl)-2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]propanoate
• CAS: 1196734-96-9
• 化学式: C₁₇H₂₄N₂O₇
• 分子量: 368.387
• InChiKey: LWDJRZUOYNFIET-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-(2-((tert-butoxycarbonyl)amino)acetamido)-3-(3,4-dihydroxyphenyl)propanoate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成 methyl (2S)-2-[(2-aminoacetyl)amino]-3-(3,4-dihydroxyphenyl)propanoate
  参考文献：
  名称：

  A novel and efficient synthesis of DOPA and DOPA peptides by oxidation of tyrosine residues with IBX

  摘要：

  An efficient route to 3,4-dihydroxylphenylalanine (DOPA) and DOPA pept des was described by oxidation of L-tyrosine and L-tyrosine derivatives with 2-iodoxybenzoic acid (IBX) DOPA was obtained after ail Situ reduction of the corresponding ortho-Cl U I none with sodium dithionite. Oxidation reactions proceeded Ill good yields and high chemo- and regio-selectivity The chirality of the DOPA residue was retained under the reaction conditions The efficiency and the selectivity of the reaction were successfully tested using recyclable polymer-supported IBX (C) 2009 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tetlet.2009.09.034
• 作为产物：
  描述：

  左旋多巴 在 氯化亚砜 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 26.0h， 生成 (S)-methyl 2-(2-((tert-butoxycarbonyl)amino)acetamido)-3-(3,4-dihydroxyphenyl)propanoate
  参考文献：
  名称：

  Synthesis of Cross-linkable 2,5-Diketopiperazine Derivatives

  摘要：

  本文描述了可交联二酮哌嗪衍生物的合成方法。通过与保护基为Boc的甘氨酸或L-酪氨酸进行多肽合成，可交联的氨基酸甲酯得以构建。在构建二酮哌嗪骨架过程中，无需对可交联功能基团（儿茶酚和苯基叠氮）进行保护。

  DOI：

  10.2174/1570178612666150629181357

文献信息

• Selective Synthesis of DOPA and DOPA Peptides by Native and Immobilized Tyrosinase in Organic Solvent
  作者：Giorgia Botta、Michela Delfino、Melissa Guazzaroni、Claudia Crestini、Silvano Onofri、Raffaele Saladino

  DOI：10.1002/cplu.201200300

  日期：2013.4

  4‐Dihydroxyphenylalanine (DOPA)‐containing peptides and proteins provide attractive design paradigms for pharmaceutical applications and engineering of synthetic polymers. An efficient and selective route to DOPA peptides by oxidation of L‐tyrosine derivatives with tyrosinase is reported. The efficiency of the procedure was tested by using successively recycled tyrosinase immobilized on Eupergit®C250L and

  含3,4-二羟基苯丙氨酸（DOPA）的肽和蛋白质为制药应用和合成聚合物的工程设计提供了诱人的设计范例。据报道，通过酪氨酸酶氧化L-酪氨酸衍生物可以有效而选择性地合成DOPA肽。通过使用固定在Eupergit®C250L上并通过逐层方法涂有聚电解质的连续回收的酪氨酸酶来测试该方法的效率。
• Synthesis of Cross-linkable 2,5-Diketopiperazine Derivatives
  作者：Takuma Yoshida、Lei Wang、Shiori Nakagawa、Zetryana Tachrim、Yasuko Sakihama、Yasuyuki Hashidoko、Makoto Hashimoto

  DOI：10.2174/1570178612666150629181357

  日期：2015.8.26

  Synthesis of cross-linkable diketopiperadine derivatives is described. Cross-linkable aamino acid methyl esters were subjected to peptide synthesis with Boc-protected glycine or L-tyrosine. No protection of cross-linkable functional groups (catechol and phenylazide) is necessary for the construction of diketopiperazine skeleton.

  本文描述了可交联二酮哌嗪衍生物的合成方法。通过与保护基为Boc的甘氨酸或L-酪氨酸进行多肽合成，可交联的氨基酸甲酯得以构建。在构建二酮哌嗪骨架过程中，无需对可交联功能基团（儿茶酚和苯基叠氮）进行保护。
• A novel and efficient synthesis of DOPA and DOPA peptides by oxidation of tyrosine residues with IBX
  作者：Roberta Bernini、Maurizio Barontini、Fernanda Crisante、Maria Cristina Ginnasi、Raffaele Saladino

  DOI：10.1016/j.tetlet.2009.09.034

  日期：2009.11

  An efficient route to 3,4-dihydroxylphenylalanine (DOPA) and DOPA pept des was described by oxidation of L-tyrosine and L-tyrosine derivatives with 2-iodoxybenzoic acid (IBX) DOPA was obtained after ail Situ reduction of the corresponding ortho-Cl U I none with sodium dithionite. Oxidation reactions proceeded Ill good yields and high chemo- and regio-selectivity The chirality of the DOPA residue was retained under the reaction conditions The efficiency and the selectivity of the reaction were successfully tested using recyclable polymer-supported IBX (C) 2009 Elsevier Ltd. All rights reserved