Cys(Acm)-OMe | 55300-64-6

• 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: Cys(Acm)-OMe
• 英文别名: Methyl (2R)-2-amino-3-[(acetamidomethyl)sulfanyl]propanoate；methyl (2R)-3-(acetamidomethylsulfanyl)-2-aminopropanoate
• CAS: 55300-64-6
• 化学式: C₇H₁₄N₂O₃S
• 分子量: 206.266
• InChiKey: NRTHUBCCPNZHNC-LURJTMIESA-N

物化性质

• 沸点：
  392.5±42.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Cys(Acm)-OMe 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成
  参考文献：
  名称：

  Efficient Gene Transfection by Histidine-Modified Chitosan through Enhancement of Endosomal Escape

  摘要：

  Chitosan has the potential to be a biocompatible gene carrier. However, the transfection efficiency of chitosan is low because of the slow endosomal escape rate. The buffering capacity of histidine in the endosomal range would help the escape of plasmid DNA (pDNA) from endosomes. In this study, histidine was introduced into chitosan to improve the transfection efficiency. Chitosan and histidine were linked by disulfide bonds provided by 2-iminothiolane and cysteine. The complexes were prepared by mixing chitosan or histidine-modified chitosan with plasmid DNA. A broader buffering range of histidine-modified chitosan was observed, and the cellular uptake of histidine-modified chitosan/pDNA complexes was higher than that of chitosan/pDNA complexes. Although chitosan/tetramethylrhodamine (TMR)-pDNA complexes were trapped in the vesicles in cytosol, TMR-pDNA carried by histidine-modified chitosan was more widely distributed in the cytosol. This result suggests that histidine can help pDNA escape from endosomes with the help of the high buffering capacity. The gene expression of histidine-modified chitosan/pDNA complexes was higher than that of chitosan/pDNA complexes. These results suggest that histidine modification improves the transfection efficiency of chitosan.

  DOI：

  10.1021/bc1000609
• 作为产物：
  描述：

  methylN-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-(acetamidomethyl)-L-cysteinate 在 三氯化铝 、 N,N-二甲基苯胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 Cys(Acm)-OMe
  参考文献：
  名称：

  在 AlCl3/N,N-二甲基苯胺试剂系统中通过调节摩尔比对 N-Fmoc-氨基酸和 N-Fmoc-二肽甲酯的 α-氨基和羧基官能团进行选择性和化学选择性脱保护

  摘要：

  N-Fmoc-α-氨基酸和 N-Fmoc-肽甲酯中的氨基和羧基官能团可以通过使用试剂系统 AlCl3/N,N-二甲基苯胺 (DMA) 进行选择性化学选择性脱保护。该过程的化学选择性是通过调节路易斯酸和 DMA 的相对摩尔比来控制的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200400321

文献信息

• Process for the manufacture of peptides containing cystine
  申请人：Ciba-Geigy Corporation

  公开号：US03994871A1

  公开（公告）日：1976-11-30

  Process for the manufacture of peptides which contain more than one disulphide bond characterized in that in one or two aminoacid sequences containing cysteine, in which disulphide bonds are to be produced, two cysteine radicals which are to be linked are protected by a mercapto-protective group R.sub.1 of the aralkyl type, two further cysteine radicals are protected by an acylaminomethyl group R.sub.2, the protective groups R.sub.1 are removed by treatment with iodine in the presence of a polyhalogenated lower aliphatic hydroxy compound or oxo compound, or a corresponding lower alkanoic acid lower alkyl ester, at the same time forming the disulphide bond between these cysteine radicals, which are protected by R.sub.1, and at any desired point after removal of the polyhalogenated compound the second disulphide bridge is formed in the usual manner.

  含有多个二硫键的肽的制造过程的特点在于，在含有半胱氨酸的一个或两个氨基酸序列中，其中要产生二硫键，两个要连接的半胱氨酸基团由苯基烷基保护基R.sub.1保护，另外两个半胱氨酸基团由酰胺甲基基团R.sub.2保护，通过在多卤代低级脂肪羟基化合物或氧化合物或相应的低级烷基酸低级酯存在下用碘处理来去除保护基R.sub.1，同时在这些由R.sub.1保护的半胱氨酸基团之间形成二硫键，在去除多卤代化合物后的任何所需点上，第二个二硫桥以通常的方式形成。
• Cystinpeptide aus (S-Acetamidomethyl-cystein)-peptiden durch Oxydation mit Jod: Die synthese voncyclo-L-cystin
  作者：B. Kamber

  DOI：10.1002/hlca.19710540319

  日期：1971.4.20

  AbstractThe conversion of S‐acetamidomethyl cysteine peptides to by a reaction with iodine is described. The method is applied in the synthesis of the hitherto unknown cyclo‐L‐cystine. The structure of this compound was confirmed by molecular weight determination, NMR. and mass spectroscopy.
• Alternative and Chemoselective Deprotection of the ?-Amino and Carboxy Functions ofN-Fmoc-Amino Acid andN-Fmoc-Dipeptide Methyl Esters by Modulation of the Molar Ratio in the AlCl3/N,N-Dimethylaniline Reagent System
  作者：Maria�Luisa Di Gioia、Antonella Leggio、Adolfo Le Pera、Angelo Liguori、Francesca Perri、Carlo Siciliano

  DOI：10.1002/ejoc.200400321

  日期：2004.11

  The amino and carboxy functions in N-Fmoc-α-amino acid and N-Fmoc-peptide methyl esters can be alternatively and chemoselectively deprotected by treatment with the reagent system AlCl3/N,N-dimethylaniline (DMA). The chemoselectivity of the process is controlled by modulating the relative molar ratio of the Lewis acid and DMA. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  N-Fmoc-α-氨基酸和 N-Fmoc-肽甲酯中的氨基和羧基官能团可以通过使用试剂系统 AlCl3/N,N-二甲基苯胺 (DMA) 进行选择性化学选择性脱保护。该过程的化学选择性是通过调节路易斯酸和 DMA 的相对摩尔比来控制的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Efficient Gene Transfection by Histidine-Modified Chitosan through Enhancement of Endosomal Escape
  作者：Kai-Ling Chang、Yuriko Higuchi、Shigeru Kawakami、Fumiyoshi Yamashita、Mitsuru Hashida

  DOI：10.1021/bc1000609

  日期：2010.6.16

  Chitosan has the potential to be a biocompatible gene carrier. However, the transfection efficiency of chitosan is low because of the slow endosomal escape rate. The buffering capacity of histidine in the endosomal range would help the escape of plasmid DNA (pDNA) from endosomes. In this study, histidine was introduced into chitosan to improve the transfection efficiency. Chitosan and histidine were linked by disulfide bonds provided by 2-iminothiolane and cysteine. The complexes were prepared by mixing chitosan or histidine-modified chitosan with plasmid DNA. A broader buffering range of histidine-modified chitosan was observed, and the cellular uptake of histidine-modified chitosan/pDNA complexes was higher than that of chitosan/pDNA complexes. Although chitosan/tetramethylrhodamine (TMR)-pDNA complexes were trapped in the vesicles in cytosol, TMR-pDNA carried by histidine-modified chitosan was more widely distributed in the cytosol. This result suggests that histidine can help pDNA escape from endosomes with the help of the high buffering capacity. The gene expression of histidine-modified chitosan/pDNA complexes was higher than that of chitosan/pDNA complexes. These results suggest that histidine modification improves the transfection efficiency of chitosan.