1-N-(4,4'-dimethoxytrityl)-D(+)-biotinol | 122224-39-9

• 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: 1-N-(4,4'-dimethoxytrityl)-D(+)-biotinol
• 英文别名: (3aR,6S,6aS)-3-[bis(4-methoxyphenyl)-phenylmethyl]-6-(5-hydroxypentyl)-3a,4,6,6a-tetrahydro-1H-thieno[3,4-d]imidazol-2-one
• CAS: 122224-39-9
• 化学式: C₃₁H₃₆N₂O₄S
• 分子量: 532.704
• InChiKey: CJAIWNOVMHELSL-AWCRTANDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  96.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-N-(4,4'-dimethoxytrityl)-D(+)-biotinol 在 叔丁基过氧化氢 、 5-(乙硫基)-1H-四唑 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 10.25h， 生成 biotinol-5'-AMP
  参考文献：
  名称：

  Improved Synthesis of Biotinol-5′-AMP: Implications for Antibacterial Discovery

  摘要：

  An improved synthesis of biotinol-5'-AMP, an acyl-AMP mimic of the natural reaction intermediate of biotin protein ligase (BPL), is reported. This compound was shown to be a pan inhibitor of BPLs from a series of clinically important bacteria, particularly Staphylococcus aureus and Mycobacterium tuberculosis, and kinetic analysis revealed it to be competitive against the substrate biotin. Biotinol-5'-AMP also exhibits antibacterial activity against a panel of clinical isolates of S. aureus and M. tuberculosis with MIC values of 1-8 and 0.5-2.5 μg/mL, respectively, while being devoid of cytotoxicity to human HepG2 cells.

  DOI：

  10.1021/ml500475n
• 作为产物：
  描述：

  D-生物素甲酯 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 1-N-(4,4'-dimethoxytrityl)-D(+)-biotinol
  参考文献：
  名称：

  A chemical method of labelling oligodeoxyribonucleotides with biotin: A single step procedure using a solid phase methodology

  摘要：

  DOI：

  10.1016/s0040-4039(00)99410-3

文献信息

• [EN] NOVEL ANTIMICROBIAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS ANTIMICROBIENS
  申请人：ADELAIDE RES & INNOVATION PTY

  公开号：WO2013040647A1

  公开（公告）日：2013-03-28

  A new class of biotin protein ligase (BPL) inhibitors that have antibacterial activity against multiple Staphylococcus aureus isolates, including clinically important methicillin-resistant S. aureus (MRSA) are disclosed that are non-toxic.

  披萨店的招牌菜是各种口味的披萨，包括经典的意大利香肠披萨、夏威夷披萨、墨西哥辣椒披萨等。
• NOVEL ANTIMICROBIAL COMPOUNDS
  申请人：MONASH UNIVERSITY

  公开号：US20140296177A1

  公开（公告）日：2014-10-02

  A new class of biotin protein ligase (BPL) inhibitors that have antibacterial activity against multiple Staphylococcus aureus isolates, including clinically important methicillin-resistant S. aureus (MRSA) are disclosed that are non-toxic.

  披露了一种新型生物素蛋白连接酶（BPL）抑制剂，对包括临床重要的甲氧西林耐药金黄色葡萄球菌（MRSA）在内的多种金黄色葡萄球菌具有抗菌活性，并且是无毒的。
• Bioreductive Markers for Hypoxic Cells: 2-Nitroimidazoles with Biotinylated 1-Substituents
  作者：Richard J. Hodgkiss、John Parrick、Manuchehr Porssa、Michael R. L. Stratford

  DOI：10.1021/jm00051a012

  日期：1994.12

  The interference by oxygen with the bioreductive metabolism and binding within cells of 2-nitroimidazoles has been used to identify hypoxic cells. Three novel compounds were synthesized with a 1-substituent containing a biotin moiety. Bound adducts of these compounds could be identified in hypoxic cells in vitro by the biotin binding proteins, avidin or streptavidin, labeled with fluorescein. The metabolism and discrimination of these compounds between well-oxygenated and hypoxic cells was evaluated by flow cytometry. Ester or amide links between the 2-nitroimidazole and the biotin were degraded in the presence of mouse serum, but a compound with a C5 hydrocarbon link was stable, and this compound was suitable for evaluation in an in vivo tumor model.
• ALVES, ANNE M.;HOLLAND, DAVID;EDGE, MICHAEL D., TETRAHEDRON LETT., 30,(1989) N3, C. 3089-3092
  作者：ALVES, ANNE M.、HOLLAND, DAVID、EDGE, MICHAEL D.

  DOI：——

  日期：——
• US9108978B2
  申请人：——

  公开号：US9108978B2

  公开（公告）日：2015-08-18