(S)-valyl-(S)-tryptophan methyl ester | 59523-93-2

• 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: (S)-valyl-(S)-tryptophan methyl ester
• 英文别名: L-Val-L-Trp-OMe；H-Val-Trp-OMe
• CAS: 59523-93-2
• 化学式: C₁₇H₂₃N₃O₃
• 分子量: 317.388
• InChiKey: WWMZNAQSMUZYPA-GJZGRUSLSA-N

物化性质

• 沸点：
  550.0±50.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  97.21
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-valyl-(S)-tryptophan methyl ester 在 氨 作用下， 以 甲醇 为溶剂， 生成 L-valyl-L-tryptophan anhydride
  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
• 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 (S)-valyl-(S)-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

• Direct Formation of Amide-Linked <i>C</i>-Glycosyl Amino Acids and Peptides via Photoredox/Nickel Dual Catalysis
  作者：Xiang-Yu Ye、Guanjie Wang、Zhichao Jin、Bin Yu、Junmin Zhang、Shichao Ren、Yonggui Robin Chi

  DOI：10.1021/jacs.3c13456

  日期：2024.2.28

  Our amide-linked C-glycosyl amino acids and peptides are synthesized through cooperative Ni-catalyzed and photoredox processes. The catalytic process generates a glycosyl radical and an amide carbonyl radical, which subsequently combine to yield the C-glycosyl products. The saccharide reaction partners encompass mono-, di-, and trisaccharides. All 20 natural amino acids, peptides, and their derivatives

  糖蛋白负责许多生物过程，包括与疾病和感染相关的生物过程。糖肽的进步已成为解开生物途径和发现新药物的有前途的策略。在这个领域，一个关键的挑战是缺乏有效的合成策略来获取糖肽和糖蛋白。在这里，我们提出了一种通过酰胺键将糖与氨基酸和肽桥接的高度简洁的方法。我们的酰胺连接C-糖基氨基酸和肽是通过镍催化和光氧化还原过程协同合成的。催化过程产生糖基自由基和酰胺羰基自由基，它们随后结合产生C-糖基产物。糖反应伴侣包括单糖、二糖和三糖。所有 20 种天然氨基酸、肽及其衍生物都可以有效地进行糖基化，产率从可接受到高不等，表现出优异的立体选择性。作为应用的实质性扩展，我们已经证明简单的C-糖基氨基酸可以作为通用的构建单元来构建具有复杂空间复杂性的C-糖肽。
• Peptide-metal complex as an asymmetric catalyst. A catalytic enantioselective cyanonhydrin synthesis.
  作者：Atsunori Mori、Hideaki Nitta、Masanobu Kudo、Shohei Inoue

  DOI：10.1016/s0040-4039(00)92163-4

  日期：1991.1

  An acyclic dipeptide ester, 2-hydroxyl-1-naphthylideneimino-(S)-valyl-(S)-tryptophane methyl ester (1a: Nap-S-Val-S-Trp-OMe), whose terminal amino group is modified to a Schiff base, is designed as a chiral auxiliary of an asymmetric catalyst. The mixture of 1 with titanium alkoxide catalyzes enantioselective hydrocyanation of benzaldehyde to afford optically active (R)-mandelonitrile with stereoselectivities up to 94:6.
• Nitta, Hideaki; Yu, Donghai; Kudo, Masanobu, Journal of the American Chemical Society, 1992, vol. 114, # 21, p. 7969 - 7975
  作者：Nitta, Hideaki、Yu, Donghai、Kudo, Masanobu、Mori, Atsunori、Inoue, Shohei

  DOI：——

  日期：——