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N-{1-[(2R,3R,4R,5R)-3-(2-tert-Butyldisulfanyl-ethoxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide | 176747-33-4

中文名称
——
中文别名
——
英文名称
N-{1-[(2R,3R,4R,5R)-3-(2-tert-Butyldisulfanyl-ethoxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide
英文别名
N-[1-[(2R,3R,4R,5R)-3-[2-(tert-butyldisulfanyl)ethoxy]-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
N-{1-[(2R,3R,4R,5R)-3-(2-tert-Butyldisulfanyl-ethoxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide化学式
CAS
176747-33-4
化学式
C22H29N3O6S2
mdl
——
分子量
495.621
InChiKey
WSKLQZPUSHLFSH-DLVXIWMQSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.5
  • 重原子数:
    33
  • 可旋转键数:
    10
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.5
  • 拓扑面积:
    171
  • 氢给体数:
    3
  • 氢受体数:
    8

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    N-{1-[(2R,3R,4R,5R)-3-(2-tert-Butyldisulfanyl-ethoxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide吡啶4-二甲氨基吡啶N,N-二异丙基乙胺 作用下, 以 二氯甲烷N,N-二甲基甲酰胺 为溶剂, 反应 8.0h, 生成 Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(2-tert-butyldisulfanyl-ethoxy)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
    参考文献:
    名称:
    Design, Synthesis, and Analysis of Yeast tRNAPhe Analogs Possessing Intra- and Interhelical Disulfide Cross-Links
    摘要:
    Disulfide cross-links have been site-specifically incorporated into unmodified yeast tRNA(Phe) by total chemical synthesis. One cross-link is between positions 1 and 72 in the amino-acid acceptor stem, and it was prepared by replacing G1 and C72 with N-3-(thioethyl)uridine. A second cross-link is in the central D-region of yeast tRNA(Phe) between 11 and 25, and it was synthesized by replacing C11 and C25 with 2'-O-alkylthiol modified cytosine residues. Air oxidation to form the cross-link at both sites occurs in 12 h and is nearly quantitative. Analysis of the crosslinked products by native and denaturing PAGE along with Pb(II) cleavage experiments demonstrates that the crosslinked molecules are monomeric and suggests that the disulfide bridges do not significantly alter the structure of the modified tRNAs relative to the parent sequence. The finding that cross-link formation between thiol-derivatized residues correlates with the position of these groups in the crystal structure of native yeast tRNA(Phe) that the modifications apparently do not perturb native structure suggests that this methodology should be applicable to the study of RNA structure, dynamics, and folding.
    DOI:
    10.1021/ja960091t
  • 作为产物:
    参考文献:
    名称:
    Design, Synthesis, and Analysis of Yeast tRNAPhe Analogs Possessing Intra- and Interhelical Disulfide Cross-Links
    摘要:
    Disulfide cross-links have been site-specifically incorporated into unmodified yeast tRNA(Phe) by total chemical synthesis. One cross-link is between positions 1 and 72 in the amino-acid acceptor stem, and it was prepared by replacing G1 and C72 with N-3-(thioethyl)uridine. A second cross-link is in the central D-region of yeast tRNA(Phe) between 11 and 25, and it was synthesized by replacing C11 and C25 with 2'-O-alkylthiol modified cytosine residues. Air oxidation to form the cross-link at both sites occurs in 12 h and is nearly quantitative. Analysis of the crosslinked products by native and denaturing PAGE along with Pb(II) cleavage experiments demonstrates that the crosslinked molecules are monomeric and suggests that the disulfide bridges do not significantly alter the structure of the modified tRNAs relative to the parent sequence. The finding that cross-link formation between thiol-derivatized residues correlates with the position of these groups in the crystal structure of native yeast tRNA(Phe) that the modifications apparently do not perturb native structure suggests that this methodology should be applicable to the study of RNA structure, dynamics, and folding.
    DOI:
    10.1021/ja960091t
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文献信息

  • Design, Synthesis, and Analysis of Yeast tRNA<sup>Phe</sup> Analogs Possessing Intra- and Interhelical Disulfide Cross-Links
    作者:Jay T. Goodwin、Scott E. Osborne、Emily J. Scholle、Gary D. Glick
    DOI:10.1021/ja960091t
    日期:1996.6.5
    Disulfide cross-links have been site-specifically incorporated into unmodified yeast tRNA(Phe) by total chemical synthesis. One cross-link is between positions 1 and 72 in the amino-acid acceptor stem, and it was prepared by replacing G1 and C72 with N-3-(thioethyl)uridine. A second cross-link is in the central D-region of yeast tRNA(Phe) between 11 and 25, and it was synthesized by replacing C11 and C25 with 2'-O-alkylthiol modified cytosine residues. Air oxidation to form the cross-link at both sites occurs in 12 h and is nearly quantitative. Analysis of the crosslinked products by native and denaturing PAGE along with Pb(II) cleavage experiments demonstrates that the crosslinked molecules are monomeric and suggests that the disulfide bridges do not significantly alter the structure of the modified tRNAs relative to the parent sequence. The finding that cross-link formation between thiol-derivatized residues correlates with the position of these groups in the crystal structure of native yeast tRNA(Phe) that the modifications apparently do not perturb native structure suggests that this methodology should be applicable to the study of RNA structure, dynamics, and folding.
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