1-(2,3-dideoxy-erythro-α-D-hexopyranosyl)thymine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(2,3-dideoxy-erythro-α-D-hexopyranosyl)thymine
• 英文别名: 1-[(2S,5S,6R)-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₁₁H₁₆N₂O₅
• 分子量: 256.258
• InChiKey: MNKMLCUOWXYQPE-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-甲氧基三苯基氯甲烷 、 1-(2,3-dideoxy-erythro-α-D-hexopyranosyl)thymine 在 吡啶 作用下， 以55%的产率得到1-(6-O-monomethoxytrityl-2,3-dideoxy-α-D-erythro-hexopyranosyl)thymine
  参考文献：
  名称：

  α-Homo-DNA and RNA Form a Parallel Oriented Non-A, Non-B-Type Double Helical Structure

  摘要：

  Cross-talking between nucleic acids is a prerequisite for information transfer. The absence of observed base pairing interactions between pyranose and furanose nucleic acids has excluded considering the former type as a (potential) direct precursor of contemporary RNA and DNA. We observed that alpha-pyranose oligonucleotides (alpha-homo-DNA) are able to hybridize with RNA and that both nucleic acid strands are parallel oriented. Hybrids between alpha-homo-DNA and DNA are less stable. During the synthesis of alpha-homo-DNA we observed extensive conversion of N6-benzoyl-5-methylcytosine into thymine under the usual deprotection conditions of oligonucleotide synthesis. Alpha-homo-DNA:RNA represents the first hybridization system between pyranose and furanose nucleic acids. The duplex formed between alpha-homo-DNA and RNA was investigated using CD, NMR spectroscopy, and molecular modeling. The general rule that orthogonal orientation of base pairs prevents hybridization is infringed. NMR experiments demonstrate that the base moieties of alpha-homo-DNA in its complex with RNA, are equatorially oriented and that the base moieties of the parallel RNA strand are pseudoaxially oriented. Modeling experiments demonstrate that the duplex formed is different from the classical A- or B-type double stranded DNA. We observed 15 base pairs in a full helical turn. The average interphosphate distance in the RNA strand is 6.2 A and in the alpha-homo-DNA strand is 6.9 A. The interstrand P-P distance is much larger than found in the typical A- and B-DNA. Most helical parameters are different from those of natural duplexes.

  DOI：

  10.1002/1521-3765(20011203)7:23<5183::aid-chem5183>3.0.co;2-h

文献信息

• α-Homo-DNA and RNA Form a Parallel Oriented Non-A, Non-B-Type Double Helical Structure
  作者：Matheus Froeyen、Eveline Lescrinier、Luc Kerremans、Helmut Rosemeyer、Frank Seela、Birgit Verbeure、Irene Lagoja、Jef Rozenski、Arthur Van Aerschot、Roger Busson、Piet Herdewijn

  DOI：10.1002/1521-3765(20011203)7:23<5183::aid-chem5183>3.0.co;2-h

  日期：2001.12.3

  Cross-talking between nucleic acids is a prerequisite for information transfer. The absence of observed base pairing interactions between pyranose and furanose nucleic acids has excluded considering the former type as a (potential) direct precursor of contemporary RNA and DNA. We observed that alpha-pyranose oligonucleotides (alpha-homo-DNA) are able to hybridize with RNA and that both nucleic acid strands are parallel oriented. Hybrids between alpha-homo-DNA and DNA are less stable. During the synthesis of alpha-homo-DNA we observed extensive conversion of N6-benzoyl-5-methylcytosine into thymine under the usual deprotection conditions of oligonucleotide synthesis. Alpha-homo-DNA:RNA represents the first hybridization system between pyranose and furanose nucleic acids. The duplex formed between alpha-homo-DNA and RNA was investigated using CD, NMR spectroscopy, and molecular modeling. The general rule that orthogonal orientation of base pairs prevents hybridization is infringed. NMR experiments demonstrate that the base moieties of alpha-homo-DNA in its complex with RNA, are equatorially oriented and that the base moieties of the parallel RNA strand are pseudoaxially oriented. Modeling experiments demonstrate that the duplex formed is different from the classical A- or B-type double stranded DNA. We observed 15 base pairs in a full helical turn. The average interphosphate distance in the RNA strand is 6.2 A and in the alpha-homo-DNA strand is 6.9 A. The interstrand P-P distance is much larger than found in the typical A- and B-DNA. Most helical parameters are different from those of natural duplexes.