环[2-甲基丙氨酰基-L-苯丙氨酰基-D-脯氨酰基-(2S,9R)-2-氨基-9-羟基-8-氧代癸酰基] | 157618-75-2

• 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
• 中文名称: 环[2-甲基丙氨酰基-L-苯丙氨酰基-D-脯氨酰基-(2S,9R)-2-氨基-9-羟基-8-氧代癸酰基]
• 英文名称: (-)-(3S,9S,14aR)-9-benzyl-3-[(R)-7-hydroxy-6-oxooctyl]-6,6-dimethyldecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10-tetraone
• 英文别名: TAN-1746；(3S,9S,14aR)-9-benzyl-3-((R)-7-hydroxy-6-oxooctyl)-6,6-dimethyldeca-hydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10-tetraone；(3S,9S,12R)-3-Benzyl-9-[(7R)-7-hydroxy-6-oxooctyl]-6,6-dimethyl-1,4,7,10-tetrazabicyclo[10.3.0]pentadecane-2,5,8,11-tetrone
• CAS: 157618-75-2
• 化学式: C₂₈H₄₀N₄O₆
• 分子量: 528.649
• InChiKey: UXOLDMJAFJDQSE-RYFAJOAYSA-N

物化性质

• 沸点：
  855.8±65.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO：可溶；乙醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  145
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  环[2-甲基丙氨酰基-L-苯丙氨酰基-D-脯氨酰基-(2S,9R)-2-氨基-9-羟基-8-氧代癸酰基] 在 盐酸 、 ruthenium trichloride 、 sodium tetrahydroborate 、 sodium periodate 作用下， 以 氯仿 、 水 、 乙腈 为溶剂， 反应 18.0h， 生成 (S)-2-氨基辛二酸
  参考文献：
  名称：

  Diheteropeptin, a Novel Substance with TGF-.BETA.-like Activity, Produced by a Fungus, Diheterospora chlamydosporia. II. Physico-chemical Properties and Structure Elucidation.

  摘要：

  通过核磁共振、质谱和化学研究，确定了 Diheterospora chlamydosporia Q58044 中的一种 TGF-β-like 活性物质 diheteropeptin (1) 的结构，它是一种新的环四肽，即环[2-氨基异丁酰-(S)-苯丙氨酰-(R)-丙氨酰-(2S, 8R, 9R)-2-amino-8, 9-dihydroxydecanoyl-]。

  DOI：

  10.7164/antibiotics.53.793
• 作为产物：
  描述：

  (S)-2-tert-butoxycarbonylamino-hex-5-enoic acid methyl ester 在 N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide 、 过氧化双月桂酰 、 四丁基氟化铵 、 1-羟基苯并三唑 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 27.0h， 生成 环[2-甲基丙氨酰基-L-苯丙氨酰基-D-脯氨酰基-(2S,9R)-2-氨基-9-羟基-8-氧代癸酰基]
  参考文献：
  名称：

  Flexible Synthesis and Evaluation of Diverse Anti-Apicomplexa Cyclic Peptides

  摘要：

  A modular approach to synthesize anti-Apicomplexa parasite inhibitors was developed that takes advantage of a pluripotent cyclic tetrapeptide scaffold capable of adjusting appendage and skeletal diversities in only a few steps (one to three steps). The diversification processes make use of selective radical coupling reactions and involve a new example of a reductive carbon nitrogen cleavage reaction with SmI2. The resulting bioactive cyclic peptides have revealed new insights into structural factors that govern selectivity between Apicomplexa parasites such as Toxoplasma and Plasmodium and human cells.

  DOI：

  10.1021/jo4001492

文献信息

• CYCLIC PEPTIDES WITH AN ANTI-PARASITIC ACTIVITY
  申请人：Wong Yung-Sing

  公开号：US20120034593A1

  公开（公告）日：2012-02-09

  The present invention relates to a method for preparing a cyclic peptide with antiparasite activity and anticancer activity. The invention also relates to this peptide as an antiparasite agent, for example in the treatment of toxoplasmosis and as an anticancer agent. The invention also relates to the use of this cyclic peptide for treating organs ex vivo before transplantation.

  本发明涉及一种制备具有抗寄生虫活性和抗癌活性的环肽的方法。该发明还涉及将该肽作为抗寄生虫剂，例如在弓形虫病的治疗中以及作为抗癌剂的用途。该发明还涉及将该环肽用于移植前体外处理器官的用途。
• Chlamydocin analogues from the soil fungus Peniophora sp.: structures and plant growth-retardant activity
  作者：Hiroko Tani、Yuzo Fujii、Hiromitsu Nakajima

  DOI：10.1016/s0031-9422(01)00209-6

  日期：2001.9

  Three chlamydocin analogues that show activity for reducing the height of rice seedlings without blotch and wilting were isolated from the culture filtrate of the soil fungus Peniophora sp. and were characterized by spectral data and chemical conversion. For two of these, it is their first isolation as natural products. The proposed role of the functional groups of the 2-amino-8-oxodecanoic acid moiety

  从土壤真菌 Peniophora sp. 的培养滤液中分离出三种衣原菌素类似物，它们显示出降低水稻幼苗高度而没有斑点和枯萎的活性。并通过光谱数据和化学转化进行表征。对于其中两个，这是它们作为天然产品的第一次隔离。这些类似物的 2-氨基-8-氧代癸酸部分的官能团的拟议作用在生长延缓活性方面进行了讨论。
• A plant growth retardant related to chlamydocin and its proposed mechanism of action
  作者：Hiroko Tani、Tamaki Honma、Yuzo Fujii、Koichi Yoneyama、Hiromitsu Nakajima

  DOI：10.1016/s0031-9422(02)00685-4

  日期：2003.4

  A comparison of the plant growth retardant activity of the chlamydocin analogues, compound 1, six derivatives from 1 and 2, and two synthetic analogues revealed that there are two types of retardant in chlamydocin analogues. One, for example in compound 1, requires an oxygen atom at C-8 of the 2-aminodecanoic acid moiety to show retardant activity. The other, for example in compound 8, requires no

  衣藻素类似物、化合物 1、来自 1 和 2 的六种衍生物以及两种合成类似物的植物生长阻滞剂活性的比较表明，衣藻素类似物有两种类型的阻滞剂。一个，例如在化合物 1 中，需要在 2-氨基癸酸部分的 C-8 处有一个氧原子以显示阻滞剂活性。另一个，例如在化合物 8 中，在 C-8 处不需要氧原子，但需要特定的烷基链长度才能发挥活性。为了确定两种类型的阻滞剂作用方式的差异，分别用化合物 1 和 8 处理水稻幼苗，在出现侏儒症后，测定它们的内源性 ABA 和 GA(1) 水平，并与对照进行比较。用 1（10 nmol/植物）处理使 ABA 水平比对照高 4 倍，并将 GA(1) 水平降低到对照的 20%。用 8 (30 nmol/植物) 处理不会影响 ABA 水平，但将 GA(1) 含量降低到对照的 5%。
• Characterization of a phytotoxic cyclotetrapeptide, a novel chlamydocin analogue, from Verticillium coccosporum
  作者：Sandeep Gupta、Galen Peiser、Toshio Nakajima、Yih-Shen Hwang

  DOI：10.1016/0040-4039(94)88061-1

  日期：1994.8

  cyclotetrapeptide containing an unusual amino acid, 2-amino-8-oxo-9-hydroxydecanoic acid, was isolated from the fungus Verticillium coccosporum. Structurally, the peptide is closely related to the known peptide chlamydocin.

  从真菌黄萎病菌（Verticillium coccosporum）中分离出一种植物毒性的环四肽，其含有一种不寻常的氨基酸2-氨基-8-氧代-9-羟基癸酸。在结构上，该肽与已知的肽衣多菌素紧密相关。
• Synthesis of 2-Amino-8-oxodecanoic Acids (Aodas) Present in Natural Hystone Deacetylase Inhibitors
  作者：Manuela Rodriquez、Ines Bruno、Elena Cini、Mauro Marchetti、Maurizio Taddei、Luigi Gomez-Paloma

  DOI：10.1021/jo0518250

  日期：2006.1.1

  Differently substituted 2-amino-8-oxodecanoic acids (Aodas), present in naturally occurring inhibitors of hystone deacetylase (HDAC), have been prepared using a convergent approach. The configuration in position 2 was derived from enantiomerically pure allylglycine or glutamic acid, whereas the stereochemistry of the substituent in position 9 derived from lactic acid or glyceraldehyde derivatives. Starting from allylglycine, (S)-Aodas, protected at the nitrogen as Boc or Fmoc, were obtained in four steps in about 30% overall yield. These products have been used to prepare a simplified analogue of a natural cyclic tetrapeptide HDAC inhibitor by SPPS.