(2'S,3'R,4R)-3-[2'-azido-3'-hydroxy-3'-(N-(triphenylmethyl)imidazol-4''-yl)propanoyl]-4-isopropyl-2-oxazolidinone | 121895-46-3

• 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: (2'S,3'R,4R)-3-[2'-azido-3'-hydroxy-3'-(N-(triphenylmethyl)imidazol-4''-yl)propanoyl]-4-isopropyl-2-oxazolidinone
• 英文别名: (4R)-3-[(2S,3R)-2-azido-3-hydroxy-3-(1-tritylimidazol-4-yl)propanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 121895-46-3
• 化学式: C₃₁H₃₀N₆O₄
• 分子量: 550.617
• InChiKey: PJYLYHRVPPZWPE-KCHLEUMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  99
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2'S,3'R,4R)-3-[2'-azido-3'-hydroxy-3'-(N-(triphenylmethyl)imidazol-4''-yl)propanoyl]-4-isopropyl-2-oxazolidinone 在 potassium tert-butylate 作用下， 以 甲醇 为溶剂， 以89%的产率得到(2S,3R)-2-Azido-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Otsuka, Masami; Nishio, Toshiyuki; Oshitari, Tetsuta, Heterocycles, 1992, vol. 33, # 1, p. 27 - 34

  摘要：

  DOI：
• 作为产物：
  描述：

  1-三苯甲基咪唑-4-甲醛 在 叠氮化锂 、 三氟甲磺酸二丁硼 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.75h， 生成 (2'S,3'R,4R)-3-[2'-azido-3'-hydroxy-3'-(N-(triphenylmethyl)imidazol-4''-yl)propanoyl]-4-isopropyl-2-oxazolidinone
  参考文献：
  名称：

  An Efficient Synthesis oferythro-β-Hydroxy-L-histidine, the Pivotal Amino Acid of Bleomycin-Fe(II)–O₂Complex

  摘要：

  (R)-3-bromoacetyl-4-isopropyl-1,3-oxazolidin-2-one 与 1-triphenylmethylimidazole-4-carbaldehyde 发生醛醇反应，然后与 LiN3 发生 SN2 反应并加氢，在有机溶剂中高效合成了赤式-β-羟基-l-组氨酸。

  DOI：

  10.1246/cl.1988.1873

文献信息

• Alteration of the Selectivity of DNA Cleavage by a Deglycobleomycin Analogue Containing a Trithiazole Moiety
  作者：Craig J. Thomas、Michael M. McCormick、Corine Vialas、Zhi-Fu Tao、Christopher J. Leitheiser、Michael J. Rishel、Xihan Wu、Sidney M. Hecht

  DOI：10.1021/ja011820u

  日期：2002.4.1

  supercoiled DNA was largely unaffected by introduction of the additional thiazole moiety. Remarkably, while no new sites of DNA cleavage were observed for this analogue, there was a strong preference for cleavage at two 5'-GT-3' sites when a 5'-(32)P end-labeled DNA duplex was used as a substrate. The alteration of sequence selectivity of cleavage was accompanied by some decrease in the potency of DNA cleavage

  博来霉素 (BLM) 抗肿瘤抗生素组以序列选择性方式影响 DNA 切割。先前的研究表明，BLM 的金属结合部分和联噻唑部分都参与了 BLM 与 DNA 的结合。金属结合结构域通常是决定 DNA 结合序列选择性的主要结构元件，但已经表明用强 DNA 结合剂替代联噻唑部分可以改变 DNA 结合和切割的序列选择性。为了进一步探索 BLM 和 DNA 相互作用的机制，合成了一种含三噻唑的 deglycoBLM 类似物，并测试了它以序列选择性方式松弛超螺旋 DNA 和切割线性双链 DNA 的能力。还研究了新 RNA 底物的裂解。三噻唑脱糖BLM A(5) 类似物的固相合成是使用包含Dde 连接器的TentaGel 树脂实现的，并从五个关键中间体精心制作而成。所得 BLM 类似物松弛超螺旋 DNA 的能力在很大程度上不受引入额外噻唑部分的影响。值得注意的是，虽然没有观察到该类似物的新 DNA 切割位点，但当使用
• Total Synthesis of Bleomycin A2 and Related Agents. 1. Synthesis and DNA Binding Properties of the Extended C-Terminus: Tripeptide S, Tetrapeptide S, Pentapeptide S, and Related Agents
  作者：Dale L. Boger、Steven L. Colletti、Takeshi Honda、Royce F. Menezes

  DOI：10.1021/ja00092a011

  日期：1994.6

  Full details of concise, diastereocontrolled syntheses of 2-5 and their incorporation into tri-, tetra-, and pentapeptide S, the C-terminus of bleomycin Alt are described. The extension of the studies to the synthesis of a complete set of tri- and tetrapeptide S structural analogs 29a,b and 43b-j is detailed, and their DNA binding constants (apparent K-B, calf thymus DNA) and apparent binding site sizes were determined. Consistent with past observations, the studies highlight the fact that the majority of the DNA binding affinity for bleomycin A(2) (1.0 X 10(5) M(-1)) and deglycobleomycin Aa (1.1 x 10(5) M(-1)) is embodied within N-BOC-tripeptide S (0.26 X 10(5) M(-1)). The additional comparisons of 29a (O.18 x 10(5) M(-1)), N-BOC-tetrapeptide S (0.21 x 10(5) M(-1)), 43h (0.20 x 10(5) M(-1)), and N-BOC-pentapeptide S (0.23 X 10(5) M(-1)) versus N-BOC-dipeptide S (0.10 x 10(5) M(-1)) indicate productive stabilizing binding interactions for the tripeptide S L-threonine subunit and substituent, illustrate that the entire pentanoic acid subunit of tetrapeptide S and its substituents do not significantly contribute to DNA binding affinity, and indicate that the entire beta-hydroxy-L-histidine subunit of pentapeptide S does not contribute to DNA binding affinity. With the exception of the L-threonine side chain substituent, the observations suggest that the tri- and tetrapeptide S substituent effects on the bleomycin A(2) DNA cleavage reaction are not due to substantial stabilizing binding interactions with duplex DNA. In addition, the measured apparent binding site sizes for bleomycin A(2)(3.8 base pairs), deglycobleomycin A(2) (3.9 base pairs), N-BOC-tripeptide S (3.6 base pairs), N-BOC-tetrapeptide S (3.7 base pairs), 43h (3.5 base pairs), and N-BOC-pentapeptide S (4.2 base pairs) versus N-BOC-dipeptide S (2.2 base pairs) and 29a (2.7 base pairs) suggest that it is the tripeptide S subunit of bleomycin A(2) that is fully bound to duplex DNA, that the tripeptide S L-threonine hydroxyethyl substituent detectably affects the agent interaction with duplex DNA, but that the presence or absence of the other tetrapeptide S and pentapeptide S backbone substituents do not substantially alter the binding site size or tripeptide S binding mode.