rac-[1-(4-methoxyphenyl)-2-(4-methylbenzylsulfanyl)ethylamino]acetic acid ethyl ester | 628298-44-2

• 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: rac-[1-(4-methoxyphenyl)-2-(4-methylbenzylsulfanyl)ethylamino]acetic acid ethyl ester
• 英文别名: [1-(4-methoxyphenyl)-2-(4-methylbenzylsulfanyl)ethylamino]acetic acid ethyl ester；Ethyl 2-[[1-(4-methoxyphenyl)-2-[(4-methylphenyl)methylsulfanyl]ethyl]amino]acetate
• CAS: 628298-44-2
• 化学式: C₂₁H₂₇NO₃S
• 分子量: 373.516
• InChiKey: YJRLDLDNKGIQPE-UHFFFAOYSA-N

物化性质

• 沸点：
  512.2±50.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  rac-[1-(4-methoxyphenyl)-2-(4-methylbenzylsulfanyl)ethylamino]acetic acid ethyl ester 在 sodium hydroxide 、 氢氟酸 、 苯甲醚 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 19.0h， 生成 2-[4-(4-甲氧基苯基)-1,3-噻唑烷-3-基]乙酸
  参考文献：
  名称：

  的合成Ñ α - （1-苯基-2-巯基乙基）氨基酸，新的构建块用于连接和环化在非半胱氨酸站点：范围和限制在肽合成

  摘要：

  用于合成和掺入一种新的和方便的方法Ñ α - （1-苯基-2-巯基乙基） -衍生的氨基酸适用于在非半胱氨酸位点的化学连接被呈现。ñ α-使用还原胺化方法容易制备甘氨酸和丙氨酸的辅助衍生物。研究了将这些衍生物掺入肽链的几种策略：偶联而不进行保护，酸不稳定的保护，碱基不稳定的保护以及使用噻唑烷衍生物的新颖保护策略。将所有氨基酸衍生物成功地偶联到各种肽树脂上，除掺入Boc保护的衍生物外，所有树脂均产生所需的肽片段。然而，两个丙氨酸衍生物非对映异构体的偶联产生一些差向异构。最后，将N-末端辅助甘氨酸和丙氨酸肽环化，并在成功去除辅助物后获得相应的天然环状肽。

  DOI：

  10.1021/jo049471k
• 作为产物：
  描述：

  4-甲基氯苄 在 正丁基锂 、 三甲基溴硅烷 、 sodium iodide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 29.17h， 生成 rac-[1-(4-methoxyphenyl)-2-(4-methylbenzylsulfanyl)ethylamino]acetic acid ethyl ester
  参考文献：
  名称：

  Derivatized Amino Acids Relevant to Native Peptide Synthesis by Chemical Ligation and Acyl Transfer

  摘要：

  Three amino acids were converted into the derivatives 5.2 (from glycine), 6.4a and 6.4b (from alanine), and 8.3a and 8.3b (from O-benzyl serine). These N-alkylated amino acids, which can be deprotected after conversion of the carboxyl into an amide, correspond to the general structure 2.1, a compound class of use in the study of peptide segment coupling by the ligation-acyl transfer method.

  DOI：

  10.1021/jo030192r

文献信息

• Extended native chemical ligation
  申请人：——

  公开号：US20040138412A1

  公开（公告）日：2004-07-15

  The invention is directed to methods and compositions for chemical ligation of components comprising a first component having a carboxythioester, and preferable an &agr;-carboxythioester, moiety and a second component having an N-substituted, and preferably an N&agr;-substituted, 2 or 3 carbon chain alkyl or aryl thiol to give a ligation product having an N-substituted amide bond at the ligation site. The reactants of the invention are chemoselective, and the alkyl or aryl thiol moiety is removable from the ligation product. Removal of the alkyl or aryl thiol gives a native amide bond at the ligation site. The methods and compositions of the invention are particularly useful for ligation of peptides and polypeptides. The ligation system of the invention is applicable to a wide variety of molecules, and thus can be exploited to generate peptides, polypeptides and other amino acid containing polymers having a native amide bond at the ligation site.

  本发明涉及一种化学连接的方法和组合物，其中第一组分具有羧基硫酯基团，首选为α-羧基硫酯基团，第二组分具有N-取代，首选为N-α-取代，2或3碳链烷基或芳基硫醇，以在连接位点形成具有N-取代酰胺键的连接产物。本发明的反应物具有化学选择性，烷基或芳基硫醇基团可从连接产物中去除。去除烷基或芳基硫醇可在连接位点形成天然酰胺键。本发明的方法和组合物特别适用于肽和多肽的连接。本发明的连接系统适用于各种分子，因此可用于生成具有连接位点处天然酰胺键的肽、多肽和其他含氨基酸的聚合物。
• EP1315738A4
  申请人：——

  公开号：EP1315738A4

  公开（公告）日：2006-06-07
• EXTENDED NATIVE CHEMICAL LIGATION
  申请人：Gryphon Therapeutics, Inc.

  公开号：EP1315738A1

  公开（公告）日：2003-06-04
• [EN] EXTENDED NATIVE CHEMICAL LIGATION<br/>[FR] LIGATURE CHIMIQUE NATURELLE ETENDUE
  申请人：GRYPHON SCIENCES

  公开号：WO2002020557A1

  公开（公告）日：2002-03-14

  The invention is directed to methods and compositions for chemical ligation of components comprising a first component having a carboxythioester, and preferable an α-carboxythioester, moiety and a second component having an N-substituted, and preferably an Nα-substituted, 2 or 3 carbon chain alkyl or aryl thiol to give a ligation product having an N-substituted amide bond at the ligation site. The reactants of the invention are chemoselective, and the alkyl or aryl thiol moiety is removable from the ligation product. Removal of the alkyl or aryl thiol gives a native amide bond at the ligation site. The methods and compositions of the invention are particularly useful for ligation of peptides and polypeptides. The ligation system of the invention is applicable to a wide variety of molecules, and thus can be exploited to generate peptides, polypeptides and other amino acid containing polymers having a native amide bond at the ligation site.