ethyl N-(2-Boc-aminoethyl)-N-(thymin-1-ylacetyl)glycinate | 149411-93-8

• 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: ethyl N-(2-Boc-aminoethyl)-N-(thymin-1-ylacetyl)glycinate
• 英文别名: N-(2-t-butoxycarbonylaminoethyl)-N-(thymin-1-ylacetyl)glycine ethyl ester；1-(Boc-Aeg)thymine ethyl ester；N-(boc-aeg)thymine ethyl ester；N-(N-Boc-2-aminoethyl)-N-[(1-thyminyl)acetyl]glycine ethyl ester；N-(t-butoxycarbonylaminoethyl)-N-(thyminylacetyl)-glycine-ethyl ester；ethyl 2-[[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]acetate
• CAS: 149411-93-8
• 化学式: C₁₈H₂₈N₄O₇
• 分子量: 412.443
• InChiKey: VOEKEOZWVQENES-UHFFFAOYSA-N

物化性质

• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl N-(2-Boc-aminoethyl)-N-(thymin-1-ylacetyl)glycinate 在 lithium hydroxide 、 水 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 Ethyl 3-[[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]-[[2-[[2-[[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]acetyl]amino]phenyl]methyl]amino]propanoate
  参考文献：
  名称：

  Backbone Modifications of Aromatic Peptide Nucleic Acid (APNA) Monomers and Their Hybridization Properties with DNA and RNA

  摘要：

  Aromatic peptide nucleic acid (APNA) monomers containing N-(2-aminobenzyl)-glycine, N-(2-aminobenzyl)-(R)- or -(S)-alanine, and N-(2-aminobenzyl)-beta -alanine moieties as part of their backbone were synthesized. These novel analogues were incorporated as a single "point mutation" in PNA hexamers, and their physicochemical properties were investigated by UV thermal denaturation and CD experiments. Destabilization in tripler formation between the PNA-APNA chimeras and complementary DNA or RNA oligomers was observed, as compared to the PNA control. The APNA monomer composed of the N-(2-aminobenzyl)-glycine backbone led to the smallest decrease in the thermal stability of the triplexes formed with DNA and RNA, while maintaining selectivity for base-pairing recognition. Since the PNA-APNA chimeras are more lipophilic than the corresponding PNA homopolymers, these oligomers may also exhibit better cell membrane permeability properties.

  DOI：

  10.1021/jo001650o
• 作为产物：
  描述：

  methyl thymin-1-ylacetate 在 sodium hydroxide 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 ethyl N-(2-Boc-aminoethyl)-N-(thymin-1-ylacetyl)glycinate
  参考文献：
  名称：

  Synthesis of Peptide Nucleic Acid Monomers Containing the Four Natural Nucleobases: Thymine, Cytosine, Adenine, and Guanine and Their Oligomerization

  摘要：

  The preparation of mixed-sequence PNAs (PNAs containing the four natural nucleobases; thymine, cytosine, adenine, and guanine) is described. The PNA monomers containing thymine, Cbz-protected cytosine, or adenine or benzyl-protected guanine were prepared via convergent syntheses. Subsequent to introduction of the carboxymethyl linker at N-1 of the pyrimidines or N-9 of the purines and suitable protection of exocyclic groups, the nucleobase derivatives were coupled to the Boc-protected backbone esters 10a or 10b and finally hydrolyzed affording the monomers 12a-d. The exocyclic amino groups of cytosine and adenine were protected with a benzyloxycarbonyl group. The exocyclic amino group of guanine was left unprotected whereas O-6 was protected as the benzyl ether. Two mixed-sequence 10-mers, each with five purines incorporated, and a mixed-sequence 15-mer Containing seven purines were assembled essentially following standard solid phase peptide synthesis protocols.

  DOI：

  10.1021/jo00098a042

文献信息

• A facile route to synthesize N-(Boc-Aminoethylglycin)thymine Ethyl Ester, application to the synthesis of PNA-oligonucleotide conjugates
  作者：Anuradha Das、Biswaranjan Pradhan

  DOI：10.1007/s12039-020-1738-y

  日期：2020.12

  to be used in various synthetic applications, and our cost-effective, highly scalable method of synthesis will expand its wider use. Graphic abstract A new method for the synthesis of Thymine-based PNA monomer precursor N-(Boc-Aeg)thymine Ethyl Ester in gram scale with high purity is reported here. In this method, the use of expensive coupling reagents is avoided.

  摘要 肽核酸寡核苷酸偶联物由于其在生物医学和诊断领域中作为抗原和分子传感器的用途而引起了极大的兴趣。有效的PNA合成方法可以降低其成本，并可以提高其广泛使用的可用性。在这里我们描述了肽核酸单体N-（Boc-氨基乙基甘氨酸）胸腺嘧啶乙基酯[乙基2-（N-（2-（（ 叔丁氧基 羰基）氨基）乙基）-2-（5-甲基- 2,4-二氧-3,4-二氢嘧啶-1（ 2H ）-基）乙酰氨基）乙酸]。N-（Boc-Aeg）胸腺嘧啶乙基酯是通过高效方法制备的，收率很高（96％），涉及核碱基胸腺嘧啶与骨架N-（Boc-氨基乙基）-N-（氯乙酰基）的直接偶联。 N-[（2-Boc-氨基）-乙基]甘氨酸乙酯与氯乙酰氯反应制得的甘氨酸盐。合成中涉及的关键中间体N-[（2-Boc-氨基）-乙基]甘氨酸乙酯已 通过 可扩展且具有成本效益的途径制备 ，产率为（98％）。据报道，胸腺嘧啶PNA单体可用于各种合成应用，而我们具有成
• Pharmaceuticals for enhanced delivery to disease targets
  申请人：Amaratunga Mark Mohan

  公开号：US20050260131A1

  公开（公告）日：2005-11-24

  Pharmaceuticals for enhanced delivery to a disease target comprises a pair of compounds. The first compound comprises a first oligopeptide conjugated to a first moiety for coupling with a diagnostic or therapeutic active agent. The second compound comprises a second oligopeptide conjugated to a targeting species having a targeting moiety capable of binding to a target. The second oligopeptide has a sequence that is complementary to a sequence of the first oligopeptide. The first and second oligopeptides can be complementary PNA sequences. The pharmaceuticals are administered into a subject in methods for diagnosing or treating a disease condition, or assessing the effectiveness of a treatment of the disease condition.

  用于增强治疗疾病靶向性的药物包括一对化合物。第一化合物包括第一寡肽与第一基团共轭，用于与诊断或治疗活性剂偶联。第二化合物包括第二寡肽与靶向物种共轭，该靶向物种具有能够结合目标的靶向基团。第二寡肽具有与第一寡肽互补的序列。第一和第二寡肽可以是互补的PNA序列。这些药物通过方法被注入到患者体内，用于诊断或治疗疾病状态，或评估疾病状态治疗的有效性。
• METHODS OF USING A CHIMERIC NUCLEIC ACID/NUCLEIC ACID ANALOGUE MOLECULE
  申请人：——

  公开号：US20020068275A1

  公开（公告）日：2002-06-06

  Chimeric molecules of nucleic acid/nucleic acid analogue, comprising a nonstandard backboned portion and a standard backboned portion having a 3′ end, useful as primers in reactions involving primer extension, such as nucleic acid amplification and sequencing.

  核酸/核酸类似物的嵌合分子，包括非标准骨架部分和具有3'末端的标准骨架部分，可用作引物参与引物扩增和测序等引物延伸反应。
• Peptide nucleic acid conjugates
  申请人：Isis Pharmaceuticals, Inc.

  公开号：US07223833B1

  公开（公告）日：2007-05-29

  A novel class of peptide nucleic acids are described which include a conjugate attached thereto. The peptide nucleic acids generally comprise ligands such as naturally occurring DNA bases attached to a peptide backbone through a suitable linker.

  描述了一种新型的肽核酸，其中包括与之结合的共轭物。这些肽核酸通常由配体组成，例如天然存在的DNA碱基，通过合适的连接剂连接到肽骨架上。
• PEPTIDE NUCLEIC ACID CONJUGATES
  申请人：ISIS PHARMACEUTICALS, INC.

  公开号：EP0804456B1

  公开（公告）日：2002-08-21