trans-cyclo-(D-tryptophanyl-L-tyrosyl) | 107911-05-7

• 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: trans-cyclo-(D-tryptophanyl-L-tyrosyl)
• 英文别名: (3S,6R)-3-[(4-hydroxyphenyl)methyl]-6-(1H-indol-3-ylmethyl)piperazine-2,5-dione
• CAS: 107911-05-7
• 化学式: C₂₀H₁₉N₃O₃
• 分子量: 349.389
• InChiKey: ZJDMXAAEAVGGSK-ZWKOTPCHSA-N

物化性质

• 沸点：
  769.8±55.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  94.2
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-cyclo-(D-tryptophanyl-L-tyrosyl) 在 盐酸 、 水 作用下， 反应 16.0h， 生成 L-酪氨酸 、 D-色氨酸
  参考文献：
  名称：

  Structure elucidation of a new natural diketopiperazine from aMicrobispora aeratastrain isolated from Livingston Island, Antarctica

  摘要：

  A new natural diketopiperazine (1) was obtained from the culture broth of Microbispora aerata strain imbas-11A, isolated from penguin excrements collected on the Antarctic Livingston Island. Compound 1 was purified consecutively by solvent extraction, silica gel column chromatography and preparative HPLC. The structure of the compound was elucidated by 1D and 2D NMR experiments and mass spectrometric investigations. The absolute configuration of compound 1 was determined by amino acid analysis and NOESY correlations. A low antiproliferative and cytotoxic effect of trans-cyclo-(D-tryptophanyl-L-tyrosyl) (1) was determined with L-929 mouse fibroblast cells, K-562 human leukemia cells and HeLa human cervix carcinoma. Trans-cyclo-(D-tryptophanyl-L-tyrosyl) (1) did not show antimicrobial activity at a concentration of 50 mu g per disc against Bacillus subtilis, Staphylococcus aureus, Streptomyces viridochromogenes, Escherichia coli, Candida albicans and Mucor miehei.

  DOI：

  10.1080/14786419.2012.665911

文献信息

• Reconstruction of pyrrolo[2,3-b]indoles carrying an α-configured reverse C3-dimethylallyl moiety by using recombinant enzymes
  作者：Wen-Bing Yin、Xiu-Lan Xie、Marco Matuschek、Shu-Ming Li

  DOI：10.1039/b922440h

  日期：——

  Nine reversely C3-prenylated pyrrolo[2,3-b]indoles were successfully prepared by using two recombinant enzymes involved in the biosynthesis of acetylaszonalenin from Neosartorya fischeri. The prenyltransferase AnaPT catalysed the conversion of six tryptophan-containing cyclic dipeptides to reversely C3-prenylated indoline derivatives. Using cyclo-L-Trp-L-Trp as substrate, both mono- and diprenylated indolines were obtained. Two of the AnaPT products were acetylated at position N1 by the acetyltransferase AnaAT. The structures of the obtained compounds were characterised by HR-ESI-MS, 1H- and 13C-NMR analyses as well as by long-range 1H-13C connectivities in heteronuclear multiple-bond correlation (HMBC) spectra after preparative isolation. Their absolute configurations were determined by analysing the 1H-1H spatial correlations in rotating-frame nuclear overhauser effect spectroscopy (ROESY).

  通过使用两种重组酶，成功制备了九种反向C3-异戊烯基化的吡咯并[2,3-b]吲哚，这些酶参与从新青霉（Neosartorya fischeri）中生物合成乙酰紫草素。异戊烯基转移酶AnaPT催化六种含色氨酸的环状二肽转化为反向C3-异戊烯基化的�
• Substrate Promiscuity of the Cyclic Dipeptide Prenyltransferases from <i>Aspergillus fumigatus</i>
  作者：Huixi Zou、Xiaodong Zheng、Shu-Ming Li

  DOI：10.1021/np800501m

  日期：2009.1.23

  This study reports that a series of tryptophan derivatives with modifications on the side chain or at the indole ring were accepted by two cyclic dipeptide prenyltransferases, CdpNPT and FtmPT1, and converted to prenylated derivatives. The structures of the enzymatic products were elucidated by NMR and MS analyses. In comparison to cyclic dipeptides, which were reversely prenylated by CdpNPT at N-1 and in a regular manner by FtmPT1 at C-2, respectively, tryptophan and its simple derivatives were prenylated reversely by both enzymes at N-1. These results demonstrated the substrate promiscuity of both enzymes.
• Structure elucidation of a new natural diketopiperazine from a<i>Microbispora aerata</i>strain isolated from Livingston Island, Antarctica
  作者：Veneta Ivanova、Hartmut Laatsch、Mariana Kolarova、Krasja Aleksieva

  DOI：10.1080/14786419.2012.665911

  日期：2013.1

  A new natural diketopiperazine (1) was obtained from the culture broth of Microbispora aerata strain imbas-11A, isolated from penguin excrements collected on the Antarctic Livingston Island. Compound 1 was purified consecutively by solvent extraction, silica gel column chromatography and preparative HPLC. The structure of the compound was elucidated by 1D and 2D NMR experiments and mass spectrometric investigations. The absolute configuration of compound 1 was determined by amino acid analysis and NOESY correlations. A low antiproliferative and cytotoxic effect of trans-cyclo-(D-tryptophanyl-L-tyrosyl) (1) was determined with L-929 mouse fibroblast cells, K-562 human leukemia cells and HeLa human cervix carcinoma. Trans-cyclo-(D-tryptophanyl-L-tyrosyl) (1) did not show antimicrobial activity at a concentration of 50 mu g per disc against Bacillus subtilis, Staphylococcus aureus, Streptomyces viridochromogenes, Escherichia coli, Candida albicans and Mucor miehei.