L-tryptophyl-D-tryptophan | 398142-70-6

• 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: L-tryptophyl-D-tryptophan
• 英文别名: L,D-ditryptophan；L-Trp-D-Trp；L-Try-D-Try；LD-ditryptophane；L-tryptophanyl-D-tryptophan；H-L-Trp-D-Trp-OH；(2R)-2-[[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]-3-(1H-indol-3-yl)propanoic acid
• CAS: 398142-70-6
• 化学式: C₂₂H₂₂N₄O₃
• 分子量: 390.442
• InChiKey: NQIHMZLGCZNZBN-FXAWDEMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  124
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-tryptophyl-D-tryptophan 、 碘甲烷 在 potassium hydrogencarbonate 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以75%的产率得到N,N,N-trimethylammonium-L-tryptophyl-D-tryptophan inner salt
  参考文献：
  名称：

  从海兔新的色氨酸来源的二肽和生物活性代谢产物海兔dactylomela

  摘要：

  Dactylamides A（1）和B（2），两个新的色氨酸衍生的二肽是从海兔Aplysia dactylomela中分离出来的，并通过光谱方法和脱氧类似物的合成进行结构表征。作为海兔的生物活性成分而分离出的异脲醛醇，别拉脲interol，它们各自的乙酸盐和aplysioviolin也进行了结构表征，并在一系列生物学分析中进行了评估。

  DOI：

  10.1016/s0040-4020(01)01044-4
• 作为产物：
  描述：

  N-苄氧羰基-L-色氨酸 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 L-tryptophyl-D-tryptophan
  参考文献：
  名称：

  Chiral Recognition of Dipeptides in a Biomembrane Model

  摘要：

  Chiral recognition of the enantiomeric couples of ditryptophan and diphenylalanine was observed by H-1 NMR spectroscopy in micelles formed by sodium N-dodecanoyl-L-prolinate. Ditryptophan showed a selective association with the Z domains of the amidic aggregates, whereas diphenylalanine did not show any selectivity in the association. Partition coefficients between water and aggregates were evaluated by diffusion NMR experiments. Intramolecular distances of ditryptophan isomers associated with chiral aggregates were obtained by ROESY experiments and were used as constraints in molecular mechanics calculations. From these calculations, information on the conformation of the peptides in the chiral aggregates was obtained.

  DOI：

  10.1021/ja0470057

文献信息

• Chiral adaptive recognition with sequence specificity of aromatic dipeptides in aqueous solution by an achiral cage
  作者：Lin Cheng、Ping Tian、Honghong Duan、Qingfang Li、Xiaowen Song、Anyang Li、Liping Cao

  DOI：10.1039/d2sc05854e

  日期：——

  dipeptides to form 1 : 2 host–guest complexes with high binding affinity (>1010 M−2), especially up to ∼1014 M−2 for TrpTrp. Given the dynamic rotational conformation of TPE units, achiral 1 can exhibit chiral adaptive responses with mirror-symmetrical circular dichroism (CD) and circularly polarized luminescence (CPL) spectra to enantiomeric dipeptides via supramolecular chirality transfer in the host–guest

  通过合成化合物或系统对肽和蛋白质进行序列特异性识别仍然是生物相容性介质中的一个巨大挑战。在这里，我们使用基于四苯乙烯的非手性八阳离子笼 ( 1 ) 作为分子受体和手性光学传感器，报告了在纯水溶液中具有芳香族二肽序列特异性的手性自适应识别 (CAR) 。1可以选择性地结合和二聚化芳香族二肽，形成 1 : 2 主客体复合物，具有高结合亲和力 (>10 10 M -2 )，尤其是高达∼10 14 M -2的 TrpTrp。鉴于 TPE 单元的动态旋转构象，非手性1可以通过主客体复合物中的超分子手性转移对对映体二肽表现出镜像对称圆二色性 (CD) 和圆偏振发光 (CPL) 光谱的手性适应性响应。此外，这种序列特异性为1的 CAR可用于分子识别含有 TrpTrp 或 PhePhe 的四肽、多肽（例如，淀粉样蛋白 β-肽1-20和生长抑素）和具有特征性 CD 的蛋白质（例如，人胰岛素）回应。
• JPH05331188A
  申请人：——

  公开号：JPH05331188A

  公开（公告）日：1993-12-14
• US3965260A
  申请人：——

  公开号：US3965260A

  公开（公告）日：1976-06-22
• Novel tryptophan-derived dipeptides and bioactive metabolites from the sea hare Aplysia dactylomela
  作者：David R Appleton、Russell C Babcock、Brent R Copp

  DOI：10.1016/s0040-4020(01)01044-4

  日期：2001.12

  Dactylamides A (1) and B (2), two new tryptophan-derived dipeptides were isolated from the sea hare Aplysia dactylomela and structurally characterised by spectroscopic methods and synthesis of deoxy-analogues. Isolaurenisol, allolaurinterol, their respective acetates and aplysioviolin, isolated as the bioactive constituents of the sea hare, were also structurally characterised and evaluated in a range

  Dactylamides A（1）和B（2），两个新的色氨酸衍生的二肽是从海兔Aplysia dactylomela中分离出来的，并通过光谱方法和脱氧类似物的合成进行结构表征。作为海兔的生物活性成分而分离出的异脲醛醇，别拉脲interol，它们各自的乙酸盐和aplysioviolin也进行了结构表征，并在一系列生物学分析中进行了评估。
• Chiral Recognition of Dipeptides in a Biomembrane Model
  作者：Cecilia Bombelli、Stefano Borocci、Federica Lupi、Giovanna Mancini、Luisa Mannina、Anna Laura Segre、Stéphane Viel

  DOI：10.1021/ja0470057

  日期：2004.10.1

  Chiral recognition of the enantiomeric couples of ditryptophan and diphenylalanine was observed by H-1 NMR spectroscopy in micelles formed by sodium N-dodecanoyl-L-prolinate. Ditryptophan showed a selective association with the Z domains of the amidic aggregates, whereas diphenylalanine did not show any selectivity in the association. Partition coefficients between water and aggregates were evaluated by diffusion NMR experiments. Intramolecular distances of ditryptophan isomers associated with chiral aggregates were obtained by ROESY experiments and were used as constraints in molecular mechanics calculations. From these calculations, information on the conformation of the peptides in the chiral aggregates was obtained.