5'-deoxy-5'-C-(4,4'-dimethoxytrityloxymethyl)thymidine | 189194-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-deoxy-5'-C-(4,4'-dimethoxytrityloxymethyl)thymidine
• 英文别名: DMT(-6)2,5-deoxy-D-eryHexf(b)-thymin-1-yl；1-[(2R,4S,5R)-5-[2-[bis(4-methoxyphenyl)-phenylmethoxy]ethyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 189194-84-1
• 化学式: C₃₂H₃₄N₂O₇
• 分子量: 558.631
• InChiKey: NQTZVERLNCGDBN-ZGIBFIJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5'-deoxy-5'-C-(4,4'-dimethoxytrityloxymethyl)thymidine 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 乙腈 为溶剂， 以87.7%的产率得到
  参考文献：
  名称：

  Phospho-carboxylic anhydride of a homologated nucleoside leads to primer degradation in the presence of a polymerase

  摘要：

  Starting from thymidine, through a series of key synthetic transformations (e.g., Wittig reaction, hydroboration, Mitsunobu reaction and TEMPO oxidation) a nucleoside homologue bearing a phospho-carboxylic anhydride group at 60 position was synthesized. The potential of polymerases to catalyze amide bond formation was investigated by using a modified primer with an amino group at 3' position and the synthesized phosphoanhydro compound as substrate. Unfortunately, we did not observe the desired product either by gel electrophoresis or mass spectrometry. In contrast, the instability of the phosphoanhydro compound could lead to pyrophosphate formation and thus, to pyrophosphorolysis of the primer rather than to primer extension. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.042
• 作为产物：
  描述：

  3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde 在 吡啶 、 甲醇 、 palladium 10% on activated carbon 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 水 、 乙腈 、 环己烯 为溶剂， 反应 53.08h， 生成 5'-deoxy-5'-C-(4,4'-dimethoxytrityloxymethyl)thymidine
  参考文献：
  名称：

  Phospho-carboxylic anhydride of a homologated nucleoside leads to primer degradation in the presence of a polymerase

  摘要：

  Starting from thymidine, through a series of key synthetic transformations (e.g., Wittig reaction, hydroboration, Mitsunobu reaction and TEMPO oxidation) a nucleoside homologue bearing a phospho-carboxylic anhydride group at 60 position was synthesized. The potential of polymerases to catalyze amide bond formation was investigated by using a modified primer with an amino group at 3' position and the synthesized phosphoanhydro compound as substrate. Unfortunately, we did not observe the desired product either by gel electrophoresis or mass spectrometry. In contrast, the instability of the phosphoanhydro compound could lead to pyrophosphate formation and thus, to pyrophosphorolysis of the primer rather than to primer extension. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.042

文献信息

• Oligodeoxynucleotides with Extended 3'- and 5'-Homologous Internucleotide Linkages.
  作者：T. Kofoed、P. B. Rasmussen、P. Valentin-Hansen、E. B. Pedersen、Kari Rissanen、Wenjun Shi、Stenbjörn Styring、Cecilia Tommos、Kurt Warncke、Bryan R. Wood

  DOI：10.3891/acta.chem.scand.51-0318

  日期：——

  3'-Deoxy-3'-C-(hydroxymethyl)thymidine (3'-DHMT) and 5'-deoxy-5'-C-(hydroxymethyl)thymidine (5'-DHMT) have been prepared and used for the synthesis of novel oligodeoxynucleotides containing extended internucleotide linkages. Enzymatic stability toward exonuclease III degradation was studied and hybridization properties were tested, The extended 3'-homologous DNA causes complete cessation of exonuclease III degradation while the extended 5'-homologous DNA shows only same decrease in degradation. Duplexes having extended internucleotide linkages show a minor decrease in hybridization stability. Tripler formation with 20-mer duplexes at pH 5.5 and high salt concentration gave almost no decrease in binding affinity when compared with unmodified tripler formation. UV experiments were also performed with oligodeoxynucleotides containing hairpin structures and bulged bases, Extended linkages in the oligodeoxynucleotides gave a small increase in T-m with sequences containing a loop, but no change or only a small decrease was observed when an extra thymidine nucleotide was incorporated in the complementary strand.
• PEPTIDE-COMPOUND CYCLIZATION METHOD
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US20210061860A1

  公开（公告）日：2021-03-04

  An object of the present invention is to provide methods of discovering drugs effective for tough targets, which have conventionally been discovered only with difficulty. The present invention relates to novel methods for cyclizing peptide compounds, and novel peptide compounds and libraries comprising the same, to achieve the above object.