Cyclo-(L)-Trp-(D)-Ala | 17079-37-7

• 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: Cyclo-(L)-Trp-(D)-Ala
• 英文别名: Cyclo(D-Ala-L-Trp-)；(3S,6R)-3-(1H-indol-3-ylmethyl)-6-methylpiperazine-2,5-dione
• CAS: 17079-37-7；19943-35-2；22216-02-0；22216-03-1；22839-21-0；22839-22-1；22839-23-2；26384-48-5
• 化学式: C₁₄H₁₅N₃O₂
• 分子量: 257.292
• InChiKey: VDMMFAOUINDEGC-PELKAZGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  74
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Cyclo-(L)-Trp-(D)-Ala 在 吡啶 、 三氟乙酸 作用下， 反应 4.0h， 生成 (1S,4R,7R,9R)-16-acetyl-4-methyl-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-triene-3,6-dione
  参考文献：
  名称：

  Stereochemical issues related to the synthesis and reactivity of pyrazino[2′,1′-5,1]pyrrolo[2,3-b]indole-1,4-diones

  摘要：

  The cyclization of all four diastereoisomers of cyclo-(Trp-Ala) to the corresponding 3,5a,6,10b,11,11a-hexahydro-2H-pyrazino[2',1'-5,1]pyrrolo[2,3-b]indoles is studied from the stereochemical point of view. Epimerization of the tryptophan stereocenter during the cyclization and during acylation reactions of the N-2 atom of the tetracyclic derivatives is discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00068-8
• 作为产物：
  描述：

  (3S)-cis-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester; hydrochloride 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.5h， 生成 Cyclo-(L)-Trp-(D)-Ala
  参考文献：
  名称：

  立体控制合成3,6-二甲基-2,3,6,7,12,12a-六氢吡嗪并[1,2-b]-β-咔啉-1,4-二酮。

  摘要：

  DOI：

  10.1021/jo971842s

文献信息

• Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)-Naseseazines A and B
  作者：Madeleine E. Kieffer、Kangway V. Chuang、Sarah E. Reisman

  DOI：10.1021/ja4023557

  日期：2013.4.17

  A copper-catalyzed arylation of tryptophan derivatives is reported. The reaction proceeds with high site- and diastereoselectivity to provide aryl pyrroloindoline products in one step from simple starting materials. The utility of this transformation is highlighted in the five-step syntheses of the natural products (+)-naseseazine A and B.

  报道了色氨酸衍生物的铜催化芳基化。该反应以高位点和非对映选择性进行，从简单的起始材料一步即可提供芳基吡咯并二氢吲哚产物。这种转化的效用在天然产物 (+)-naseseazine A 和 B 的五步合成中得到了强调。
• Prenylation at the indole ring leads to a significant increase of cytotoxicity of tryptophan-containing cyclic dipeptides
  作者：Beate Wollinsky、Lena Ludwig、Alexandra Hamacher、Xia Yu、Matthias U. Kassack、Shu-Ming Li

  DOI：10.1016/j.bmcl.2012.04.119

  日期：2012.6

  lines. Preliminary results have been clearly shown that prenylation at C2 led to a significant increase of the cytotoxicity of the tested cyclic dipeptides in all the 14 cases. The second amino acid and the stereochemistry of tryptophan moiety of the cyclic dipeptides showed less influence on the cytotoxicity of the tested compounds.

  在纯化的重组磷酸二甲基烯丙酯存在下，将十四个含色氨酸的环二肽1a - 14a（包括环-Trp-Pro和环-Trp-Ala的所有四个立体异构体）转化为C2规则的烯丙基化衍生物1b – 14b。 FtmPT1作为催化剂。在HPLC上以制备规模分离出酶产物，并通过NMR和MS分析阐明其结构。 用人白血病K562和卵巢癌A2780 sens和A2780 CisR细胞系测试了烯丙基化产物及其底物的细胞毒性作用。初步结果已清楚地表明，在所有14例病例中，C2的异戊烯基化都会导致所测试的环二肽的细胞毒性显着增加。环状二肽的第二种氨基酸和色氨酸部分的立体化学对受试化合物的细胞毒性影响较小。
• Breaking the regioselectivity of indole prenyltransferases: identification of regular C3-prenylated hexahydropyrrolo[2,3-b]indoles as side products of the regular C2-prenyltransferase FtmPT1
  作者：Beate Wollinsky、Lena Ludwig、Xiulan Xie、Shu-Ming Li

  DOI：10.1039/c2ob26149a

  日期：——

  mixtures of FtmPT1 with these cyclic dipeptides revealed the presence of additional product peaks in the HPLC chromatograms. Seven regularly C3-prenylated hexahydropyrrolo[2,3-b]indoles were isolated and identified by HR-ESI-MS and NMR analyses including HMBC, HMQC and NOESY experiments. Further experiments proved that the C2- and C3-prenylated products are both independent enzyme products. To the best of

  从异戊烯转移FtmPT1烟曲霉涉及烟曲霉毒素型生物碱的生物合成和催化brevianamide F的常规C 2异戊烯化（环-大号-Trp-大号-Pro）。已经显示出FtmPT1还在吲哚核的C-2处在二甲基烯丙基二磷酸的存在下接受许多其他的含色氨酸的环状二肽并对其进行异戊酸酯化。FtmPT1与这些环状二肽的孵育混合物的详细分析显示，HPLC色谱图中还存在其他产物峰。七个规则的C3烯丙基化的六氢吡咯并[2,3- b通过HR-ESI-MS和NMR分析（包括HMBC，HMQC和NOESY实验）分离和鉴定吲哚。进一步的实验证明，C2-和C3-异戊二烯化产物都是独立的酶产物。就我们所知，这是关于定期形成C3戊烯基化二氢吲哚的酶促形成的首次报道。提出了C 2和C 3烯丙基化衍生物的反应机理。
• Cyclic tautomers of tryptophans and tryptamines. VIII. Cyclic tautomers of cyclo-L-prolyl-L-tryptophyl and related compounds.
  作者：MIKIO TANIGUCHI、ICHIRO YAMAMOTO、MASAKO NAKAGAWA、TOHRU HINO

  DOI：10.1248/cpb.33.4783

  日期：——

  Two diastereomers (6 and 7) of the cyclic tautomer of cyclo-L-propyl-L-tryptophyl (5) have been prepared by dissolving 5 in 85% phosphoric acid or trifluoroacetic acid. The stable isomer (6) was obtained in 89% yield on the acid treatment of 5 at room temperature. Cyclic tautomers (15 and 17) of the related 2, 5-piperazinediones (14 and 16) have also been prepared. Hydroxylation of the N-acetyl cyclic tautomers (8 and 9) with lead tetraacetate in trifluoroacetic acid followed by methylation gave the 8- and 9-methoxy derivatives (18, 19, 21, and 22) in moderate yields. The 9-methoxy derivative (22) was the major product of the oxidation of 9. On the other hand, oxidation of 5 in trifluoroacetic acid with lead tetraacetate followed by reduction with zinc gave the 8-hydroxy derivative (28) selectively in good yield via the cyclic tautomer (26) and the quinoneimine (27).

  通过将 5 溶解在 85% 的磷酸或三氟乙酸中，制备出了环-L-丙基-L-色氨酰（5）环状同分异构体的两种非对映异构体（6 和 7）。在室温下对 5 进行酸处理后，得到了稳定的异构体（6），收率为 89%。相关的 2，5-哌嗪二酮（14 和 16）的环状同分异构体（15 和 17）也已制备出来。用四乙酸铅在三氟乙酸中对 N-乙酰基环状同系物（8 和 9）进行羟基化反应，然后进行甲基化反应，得到了 8-和 9-甲氧基衍生物（18、19、21 和 22），收率中等。另一方面，用四乙酸铅在三氟乙酸中氧化 5，然后用锌还原，通过环状同分异构体 (26) 和醌亚胺 (27)，选择性地得到 8-羟基衍生物 (28)，收率很高。
• Stereocontrolled Synthesis of 3,6-Dimethyl- 2,3,6,7,12,12a-hexahydropyrazino[1,2-<i>b</i>]-β- carboline-1,4-diones
  作者：Antonio Madrigal、Mercedes Grande、Carmen Avendaño

  DOI：10.1021/jo971842s

  日期：1998.4.1