L-leucyl-L-leucyl-L-leucyl-L-leucyl-L-leucyl-L-leucine | 18867-82-8

• 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: L-leucyl-L-leucyl-L-leucyl-L-leucyl-L-leucyl-L-leucine
• 英文别名: Leu-Leu-Leu-Leu；(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-azaniumyl-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoate
• CAS: 18867-82-8
• 化学式: C₂₄H₄₆N₄O₅
• 分子量: 470.653
• InChiKey: REJJLEDUDOYKOO-MUGJNUQGSA-N

物化性质

• 沸点：
  720.7±60.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  151
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  L-leucyl-L-leucyl-L-leucyl-L-leucyl-L-leucyl-L-leucine 在 四乙基氯化铵 、 三乙胺 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以52%的产率得到
  参考文献：
  名称：

  Chloride-Assisted Peptide Macrocyclization

  摘要：

  The role of the Cl- anion as a templating agent for the synthesis of cyclopeptides was assessed through the preparation of three new homocyclolysines and other six cyclic peptides by head-to-tail lactamization. Isolated yields of products obtained by chloride-templating approach were considerably higher than those gained by a cation-promoted procedure, whereby, in some cases, only the anion-assisted synthesis yielded the desired cyclopeptides.

  DOI：

  10.1021/acs.orglett.0c00036
• 作为产物：
  描述：

  ((S)-2-氨基-4-甲基戊酰基)-L-亮氨酸甲酯盐酸盐 在 lithium hydroxide monohydrate 、 palladium 10% on activated carbon 、 氢气 、 1-羟基苯并三唑 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.66h， 生成 L-leucyl-L-leucyl-L-leucyl-L-leucyl-L-leucyl-L-leucine
  参考文献：
  名称：

  Chloride-Assisted Peptide Macrocyclization

  摘要：

  The role of the Cl- anion as a templating agent for the synthesis of cyclopeptides was assessed through the preparation of three new homocyclolysines and other six cyclic peptides by head-to-tail lactamization. Isolated yields of products obtained by chloride-templating approach were considerably higher than those gained by a cation-promoted procedure, whereby, in some cases, only the anion-assisted synthesis yielded the desired cyclopeptides.

  DOI：

  10.1021/acs.orglett.0c00036

文献信息

• CYTOTOXIC AGENTS COMPRISING NEW ANSAMITOCIN DERIVATIVES
  申请人：ImmunoGen, Inc.

  公开号：US20160058882A1

  公开（公告）日：2016-03-03

  New ansamitocin derivatives bearing a linking group are disclosed. Also disclosed are methods for the synthesis of these new ansamitocin derivatives and methods for their linkage to cell-binding agents. The ansamitocin derivative-cell-binding agent conjugates are useful as therapeutic agents, which are delivered specifically to target cells and are cytotoxic. These conjugates display vastly improved therapeutic efficacy in animal tumor models compared to the previously described agents.

  披露了带有连接基团的新型安沙米托辛衍生物。还披露了合成这些新型安沙米托辛衍生物的方法以及它们与细胞结合剂的连接方法。安沙米托辛衍生物-细胞结合剂偶联物作为治疗剂非常有用，它们能特异性地传递到目标细胞并具有细胞毒性。与先前描述的药物相比，这些偶联物在动物肿瘤模型中显示出显著提高的治疗效果。
• Mechanism study on the Oligomerization of Amino Acids into Peptides by Phosphorus Trichloride
  作者：Wenjie Zhao、Dongxin Zhao、Kui Lu

  DOI：10.1080/10426500701807467

  日期：2008.1.14

  As treated by phosphorus trichloride, amino acids could oligomerize into polypeptides. Based on the results obtained by 31P-NMR and ESI-MS/MS, a possible reaction mechanism was proposed. The mechanism might undergo a penta-coordinated phosphorus intermediat. The activated amino acid was a five-membered cyclic penta-coordinated phosphorus intermediate. The nucleophilic attack of the amino group from

  经三氯化磷处理后，氨基酸可寡聚化为多肽。基于31P-NMR和ESI-MS/MS的结果，提出了可能的反应机理。该机制可能会经历五配位的磷中间体。活化的氨基酸是五元环状五配位磷中间体。氨基酸或肽的氨基对中间体羰基的亲核攻击导致肽的形成并释放出一当量的二氯化磷酸。反应序列的重复产生了一系列寡肽。
• A Novel<scp>L</scp>-Amino Acid Ligase from<i>Bacillus subtilis</i>NBRC3134 Catalyzed Oligopeptide Synthesis
  作者：Kuniki KINO、Toshinobu ARAI、Daisuke TATEIWA

  DOI：10.1271/bbb.90649

  日期：2010.1.23

  l-Amino acid ligase catalyzes dipeptide synthesis from unprotected l-amino acids in an ATP-dependent manner. We have purified a new l-amino acid ligase, RizA, which synthesizes dipeptides whose N-terminus is Arg, from Bacillus subtilis NBRC3134, a microorganism that produces a rhizocticin peptide antibiotic. It was suggested that RizA is probably involved in rhizocticin biosynthesis. In this study, we performed sequence analysis of unknown regions around rizA, and newly identified a gene that encodes a protein that possesses an ATP-grasp motif upstream of rizA. This gene was designated rizB, and its recombinant protein was prepared. Recombinant RizB synthesized homo-oligomers of branched-chain l-amino acids and l-methionine consisting of two to five amino acids in an ATP-dependent manner. RizB also synthesized various heteropeptides. Further examination showed that RizB might elongate a peptide chain at the N-terminus. This is the first report on an l-amino acid ligase catalyzing oligopeptide synthesis.

  l-氨基酸连接酶以一种 ATP 依赖性方式催化未受保护的 l-氨基酸合成二肽。我们从生产根肿灵多肽抗生素的枯草芽孢杆菌 NBRC3134 中纯化出一种新的 l-氨基酸连接酶 RizA，它能合成 N 端为 Arg 的二肽。有研究认为，RizA 可能参与了根皮素的生物合成。在本研究中，我们对 rizA 周围的未知区域进行了序列分析，新发现了一个编码具有 ATP 抓取基序的蛋白质的基因，该基因位于 rizA 的上游。该基因被命名为 rizB，并制备了其重组蛋白。重组 RizB 以 ATP 依赖性方式合成由 2 至 5 个氨基酸组成的支链 l-氨基酸和 l-蛋氨酸的同源异构体。RizB 还能合成各种杂肽。进一步研究表明，RizB 可能会在 N 端延长肽链。这是首次报道一种催化寡肽合成的 l-氨基酸连接酶。
• US9090629B2
  申请人：——

  公开号：US9090629B2

  公开（公告）日：2015-07-28
• [EN] CYTOTOXIC AGENTS COMPRISING NEW ANSAMITOCIN DERIVATIVES<br/>[FR] AGENTS CYTOTOXIQUES COMPRENANT DE NOUVEAUX DÉRIVÉS D'ANSAMITOCINE
  申请人：IMMUNOGEN INC

  公开号：WO2012061590A1

  公开（公告）日：2012-05-10

  New ansamitocin derivatives bearing a linking group are disclosed. Also disclosed are methods for the synthesis of these new ansamitocin derivatives and methods for their linkage to cell-binding agents. The ansamitocin derivative- cell-binding agent conjugates are useful as therapeutic agents, which are delivered specifically to target cells and are cytotoxic. These conjugates display vastly improved therapeutic efficacy in animal tumor models compared to the previously described agents.