Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(9H-fluoren-9-ylmethoxycarbonylamino)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester | 728911-31-7

• 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: Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(9H-fluoren-9-ylmethoxycarbonylamino)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-(9H-fluoren-9-ylmethoxycarbonylamino)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate
• CAS: 728911-31-7
• 化学式: C₂₉H₂₉Cl₃N₂O₁₀
• 分子量: 671.916
• InChiKey: ILYNDVWYCVBVRQ-ZFXZZAOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  160
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(9H-fluoren-9-ylmethoxycarbonylamino)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3S,4R,5R,6R)-5-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-(acetoxymethyl)-6-(((R)-1-(5,8-diacetoxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate
  参考文献：
  名称：

  Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin

  摘要：

  The N-acetyl glucosaminosides of shikonin/alkannin were synthesized by chemical glycosylation, which provided an ideal approach to resolve the mixture of enantiomeric shikonin and alkannin co-existed in the Chinese herbs. The glycosylated shikonin and alkannin exhibited stronger binding activity to human telomeric G-quadruplex DNA than their parent structures. This research indicated that glycosylation of natural product with amino sugars is an effective strategy to improve their DNA-binding affinity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.143
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 吡啶 、 碳酸氢钠 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 肼 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(9H-fluoren-9-ylmethoxycarbonylamino)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin

  摘要：

  The N-acetyl glucosaminosides of shikonin/alkannin were synthesized by chemical glycosylation, which provided an ideal approach to resolve the mixture of enantiomeric shikonin and alkannin co-existed in the Chinese herbs. The glycosylated shikonin and alkannin exhibited stronger binding activity to human telomeric G-quadruplex DNA than their parent structures. This research indicated that glycosylation of natural product with amino sugars is an effective strategy to improve their DNA-binding affinity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.143

文献信息

• Development of new simple molecular probes of DNA bulged structures
  作者：Ziwei Xiao、Lizzy S. Kappen、Irving H. Goldberg

  DOI：10.1016/j.bmcl.2006.03.006

  日期：2006.6

  NCSi-gb is a neocarzinostatin chromophore (NCS-chrom) metabolite which binds strongly to certain two-base DNA bulges. Compared with previously reported NCSi-gb analogues, a new analogue with a different aminoglycoside position was synthesized, and it showed strong fluorescence and improved binding and sequence selectivity to DNA bulges. The N-dimethylated form of this analogue had a similar binding

  NCSi-gb是新碳抑制素发色团（NCS-chrom）代谢产物，可与某些两碱基DNA凸起牢固结合。与以前报道的NCSi-gb类似物相比，合成了具有不同氨基糖苷位置的新类似物，它显示出强荧光，并改善了对DNA凸起的结合和序列选择性。该类似物的N-二甲基化形式具有相似的结合模式，并且竞争性地抑制了NCS-chrom的凸起特异性切割。
• On-Chip Synthesis and Label-Free Assays of Oligosaccharide Arrays
  作者：Lan Ban、Milan Mrksich

  DOI：10.1002/anie.200704998

  日期：2008.4.21
• Convenient Synthesis of NCS−Chromophore Metabolite Isosteres:  Binding Agents for Bulged DNA Microenvironments
  作者：Yiqing Lin、Graham B. Jones、Geum-Sook Hwang、Lizzy Kappen、Irving H. Goldberg

  DOI：10.1021/ol0400591

  日期：2005.1.1

  A designed molecule with capacity to bind DNA bulges (20) has been prepared from readily available starting materials. The spirocyclic template was modeled on a metabolite of neocarzinostatin chromophore (NCSi-gb) and is equipped with functionality to enable convenient bioassay. Preliminary studies confirm binding at specific bulged sequences and induction of polymerase-mediated slippage events. The target compound offers a convenient means to study affinity for unique bulged motifs and for use as a molecular biology reagent.
• A bulge binding agent with novel wedge-shape topology for stimulation of DNA triplet repeat strand slippage synthesis
  作者：Liangliang Liu、Heyang Li、Long Yi、Xing Yang、Xin Wen、Zhen Xi

  DOI：10.1016/j.bmcl.2008.10.038

  日期：2008.12

  Expansion of DNA repeat sequences is associated with many human genetic diseases. Bulged DNA structures have been implicated as intermediates in DNA slippage within the DNA repeat regions. Herein a bulge binding agent with novel wedge-shape topology of the aromatic moiety was designed and synthesized. The compound-bulge DNA interactions were characterized via UV melting experiments, circular dichroism and were quantitated by surface plasmon resonance with K-d of 41.5 mu M. This compound showed remarkable stimulation for DNA triplet repeat strand slippage synthesis in vitro. (C) 2008 Elsevier Ltd. All rights reserved.
• Preparation of alkylation agents for bulged DNA microenvironments
  作者：Farid S. Fouad、Zhen Xi、Irving H. Goldberg、Graham B. Jones

  DOI：10.1016/j.bmcl.2004.03.092

  日期：2004.6

  A designed molecule with capacity to alkylate DNA bulges has been prepared from readily available starting materials. The spirocyclic template utilized was designed on the basis of established architectures, and equipped with a mustard alkylating group. Preliminary studies confirm alkylation of specific bulged sequences, paving the way for second generation substrates with higher affinity.