{[(R)-2-tert-Butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propyl]-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid | 887628-10-6

• 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: {[(R)-2-tert-Butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propyl]-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid
• 英文别名: 2-[[(2R)-3-[(4-methoxyphenyl)methylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]amino]acetic acid
• CAS: 887628-10-6
• 化学式: C₂₅H₃₄N₄O₈S
• 分子量: 550.633
• InChiKey: XPGULJWXKWNXEW-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  180
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  {[(R)-2-tert-Butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propyl]-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid 、 乙酸酐 、 N-[2-(3,4-二氢-5-甲基-2,4-二氧代-1(2H)-嘧啶基)乙酰基]-N-[2-[[(1,1-二甲基乙氧基)羰基]氨基]乙基]-甘氨酸 生成 N-[2-(2-{((R)-2-Acetylamino-3-mercapto-propyl)-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetylamino)-ethyl]-N-carbamoylmethyl-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetamide 、
  参考文献：
  名称：

  Synthesis of thiol-modified peptide nucleic acids designed for post-assembly conjugation reactions

  摘要：

  Two orthogonally protected PNA monomers were prepared having the mercaptomethyl moiety attached to the PNA backbone. These building blocks were employed in solid-phase PNA synthesis and it was shown that Boc/S-p-methoxybenzyl protection scheme was only satisfactory for the introduction of N-terminal thiol modification while the Fmoc/S-butylthio protected monomer proved to be amenable to elongation. The mercaptomethyl modification did not influence the thermal stability of a PNA/RNA duplex. The feasibility of PNA-PNA native ligation was demonstrated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.065
• 作为产物：
  描述：

  Boc-S-(4-甲氧基苄基)-L-半胱氨酸 在 molecular sieve lithium hydroxide 、 lithium aluminium tetrahydride 、 molecular sieve 、 sodium cyanoborohydride 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 1-羟基苯并三唑一水物 、 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 甲醇 、 乙醚 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.58h， 生成 {[(R)-2-tert-Butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propyl]-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid
  参考文献：
  名称：

  Synthesis of thiol-modified peptide nucleic acids designed for post-assembly conjugation reactions

  摘要：

  Two orthogonally protected PNA monomers were prepared having the mercaptomethyl moiety attached to the PNA backbone. These building blocks were employed in solid-phase PNA synthesis and it was shown that Boc/S-p-methoxybenzyl protection scheme was only satisfactory for the introduction of N-terminal thiol modification while the Fmoc/S-butylthio protected monomer proved to be amenable to elongation. The mercaptomethyl modification did not influence the thermal stability of a PNA/RNA duplex. The feasibility of PNA-PNA native ligation was demonstrated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.065

文献信息

• Synthesis of thiol-modified peptide nucleic acids designed for post-assembly conjugation reactions
  作者：Martijn C. de Koning、Lene Petersen、Jimmy J. Weterings、Mark Overhand、Gijsbert A. van der Marel、Dmitri V. Filippov

  DOI：10.1016/j.tet.2006.01.065

  日期：2006.4

  Two orthogonally protected PNA monomers were prepared having the mercaptomethyl moiety attached to the PNA backbone. These building blocks were employed in solid-phase PNA synthesis and it was shown that Boc/S-p-methoxybenzyl protection scheme was only satisfactory for the introduction of N-terminal thiol modification while the Fmoc/S-butylthio protected monomer proved to be amenable to elongation. The mercaptomethyl modification did not influence the thermal stability of a PNA/RNA duplex. The feasibility of PNA-PNA native ligation was demonstrated. (c) 2006 Elsevier Ltd. All rights reserved.