cyclo-D-alanyl-L-typthophyl | 26384-48-5

• 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-D-alanyl-L-typthophyl
• 英文别名: 3-indol-3-ylmethyl-6-methyl-piperazine-2,5-dione；3-Indol-3-ylmethyl-6-methyl-piperazin-2,5-dion；Cyclo<(D,L-Trp)-Ala>；Cycl(Ala-Trp)；c-Ala-Trp；Cyclo[(D,L-Trp)-Ala]；3-(1H-Indol-3-ylmethyl)-6-methyl-2,5-piperazinedione；3-(1H-indol-3-ylmethyl)-6-methylpiperazine-2,5-dione
• CAS: 26384-48-5
• 化学式: C₁₄H₁₅N₃O₂
• 分子量: 257.292
• InChiKey: VDMMFAOUINDEGC-UHFFFAOYSA-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-D-alanyl-L-typthophyl 以15%的产率得到
  参考文献：
  名称：

  BOCCHI V.; CASNATI G.; MARCHELLI R., TETRAHEDRON, 1978, 34, NO 7, 929-932

  摘要：

  DOI：
• 作为产物：
  描述：

  L-色氨酸甲酯盐酸盐 在 钯 氨 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 为溶剂， 生成 cyclo-D-alanyl-L-typthophyl
  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

• Abderhalden; Baumann, Chemische Berichte, 1908, vol. 41, p. 2859
  作者：Abderhalden、Baumann

  DOI：——

  日期：——
• Gaudiano; Ricca, Gazzetta Chimica Italiana, 1957, vol. 87, p. 789,793
  作者：Gaudiano、Ricca

  DOI：——

  日期：——
• Anti-Inflammatory and Anti-Allergy Extracts from Nettle
  申请人：Alberte Randall S.

  公开号：US20100009927A1

  公开（公告）日：2010-01-14

  The present invention relates in part to nettle extracts that are useful for treating or preventing seasonal allergies, allergic rhinitis, and other inflammatory conditions.
• Abderhalden; Sickel, Hoppe-Seyler´s Zeitschrift für physiologische Chemie, 1927, vol. 171, p. 96,99
  作者：Abderhalden、Sickel

  DOI：——

  日期：——
• 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.