D-alanyl-L-tryptophan methyl ester | 204980-52-9

• 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: D-alanyl-L-tryptophan methyl ester
• 英文别名: methyl (2S)-2-[[(2R)-2-aminopropanoyl]amino]-3-(1H-indol-3-yl)propanoate
• CAS: 204980-52-9
• 化学式: C₁₅H₁₉N₃O₃
• 分子量: 289.334
• InChiKey: KQTYXKRCHXEGPS-RNCFNFMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  D-alanyl-L-tryptophan methyl ester 在 Ammonium hydroxide 作用下， 以 水 为溶剂， 反应 14.0h， 以66%的产率得到(3S,8aS)-3-(1H-吲哚-3-基甲基)-2,3,6,7,8,8a-六氢吡咯并[2,1-f]吡嗪-1,4-二酮
  参考文献：
  名称：

  色氨酸衍生物的铜催化非对映选择性芳基化：(+)-Naseseazines A 和 B 的全合成

  摘要：

  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。

  DOI：

  10.1021/ja4023557
• 作为产物：
  描述：

  L-色氨酸甲酯盐酸盐 在 钯 氢气 、 N,N'-二环己基碳二亚胺 作用下， 生成 D-alanyl-L-tryptophan methyl ester
  参考文献：
  名称：

  Conformational effects in reversed-phase liquid chromatographic separation of diastereomers of cyclic dipeptides

  摘要：

  The capacity factors, k', of 11 cyclic dipeptides (X-Y) including diastereomers have been determined on an RP-HPLC column in 30% and 50% methanol and 10%, 30%, and 50% acetonitrile solutions. These factors are roughly correlated with hydrophobic parameters, such as octanol-water partition coefficients estimated and k' values for alcohols. For a pair of diastereomers of cyclic (L-X-L-Phe) and (L-X-D-Phe) derivatives k'LL is larger than k'LD, and for cyclic (D-Ala-L-Trp) and (L-Ala-L-Trp) k'LL is smaller than k'DL, particularly in highly aqueous solutions. These elution orders can be well predicted by the holistic molecular surface area approach which takes into account the folded structures of cyclic dipeptides. The present results will be useful for prediction of the log k' values of larger peptides and the hydrophobicity and related properties of peptides.

  DOI：

  10.1021/ac00062a010

文献信息

• 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
• 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。
• Conformational effects in reversed-phase liquid chromatographic separation of diastereomers of cyclic dipeptides
  作者：Noriaki. Funasaki、Sakae. Hada、Saburo. Neya

  DOI：10.1021/ac00062a010

  日期：1993.7.15

  The capacity factors, k', of 11 cyclic dipeptides (X-Y) including diastereomers have been determined on an RP-HPLC column in 30% and 50% methanol and 10%, 30%, and 50% acetonitrile solutions. These factors are roughly correlated with hydrophobic parameters, such as octanol-water partition coefficients estimated and k' values for alcohols. For a pair of diastereomers of cyclic (L-X-L-Phe) and (L-X-D-Phe) derivatives k'LL is larger than k'LD, and for cyclic (D-Ala-L-Trp) and (L-Ala-L-Trp) k'LL is smaller than k'DL, particularly in highly aqueous solutions. These elution orders can be well predicted by the holistic molecular surface area approach which takes into account the folded structures of cyclic dipeptides. The present results will be useful for prediction of the log k' values of larger peptides and the hydrophobicity and related properties of peptides.