(R)-phenylglycyl-(R)-phenylglycine | 85635-36-5

• 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: (R)-phenylglycyl-(R)-phenylglycine
• 英文别名: Glycine, (2R)-2-phenylglycyl-2-phenyl-, (2R)-；(2R)-2-[[(2R)-2-amino-2-phenylacetyl]amino]-2-phenylacetic acid
• CAS: 85635-36-5
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: UYKXJEVQVZFVPB-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对-氯苯基甲基亚砜 、 (R)-phenylglycyl-(R)-phenylglycine 在 盐酸 、 sodium hydroxide 作用下， 生成
  参考文献：
  名称：

  Enantioselective Inclusion of Methyl Phenyl Sulfoxides and Benzyl Methyl Sulfoxides by (R)-Phenylglycyl-(R)-phenylglycine and the Crystal Structures of the Inclusion Cavities

  摘要：

  Crystalline (R)-phenylglycyl-(R)-phenylglycine [(R,R)-1] includes methyl phenyl sulfoxides (2 and 3) and benzyl methyl sulfoxides (4) with high enantioselectivity. The dipeptide exhibited different stereoselectivity depending on four structural isomers of methyl tolyl sulfoxide (C8H10OS): R for methyl 2-tolyl sulfoxide, S for methyl 3-tolyl sulfoxide, and racemic for methyl 4-tolyl sulfoxide. A structural isomer, benzyl methyl sulfoxide, was included in racemic form. Chlorophenyl methyl sulfoxides 3 (C7H7ClOS) with a similar volume showed the same enantioselectivity for their recognition. By single-crystal X-ray analyses of these inclusion compounds, it was elucidated that (R,R)-1 molecules self-assembled to form layer structures and included the sulfoxides between these layers and that the origin of the enantioselectivity based on chiral cavities was induced by conformation of the C-terminal phenyl group of the dipeptide. The relative position between the ammonio proton and the C-terminal phenyl group in one molecule of the dipeptide determined the stereochemistry of the methyl sulfinyl groups to be recognized. Various positional isomers of methyl xylyl sulfoxide having the formula of C9H12OS were subjected to the enantioselective inclusion by (R,R)-1 crystals and these results are also discussed.

  DOI：

  10.1021/jo991051l
• 作为产物：
  描述：

  左旋苯甘氨酸 在 钯 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 生成 (R)-phenylglycyl-(R)-phenylglycine
  参考文献：
  名称：

  Asymmetric recognition of 1-arylethylamines by (R)-phenylglycyl-(R)-phenylglycine and its mechanism

  摘要：

  An unprotected dipeptide, (R)-phenylglycyl-(R)-phenylglycine, which is insoluble in water, was shown to be an excellent resolving reagent for racemic 1-arylethylamines. By simply stirring the mixture of the dipeptide and racemic 1-phenylethylamine in presence of water, asymmetric recognition occurred to give a salt of (S)-1-phenylethylamine (95% ee) and the dipeptide. X-Ray crystallographic study of the salt elucidated the crystal structure of the diastereomeric salt, where hydrogen bonding and hydrophobic interaction between the dipeptide and amines play important roles in the construction of layers. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00247-4

文献信息

• Specific Inclusion of 1,2-Dimethoxybenzene Derivatives by Crystalline (<i>R</i>)-Arylglycyl-(<i>R</i>)-phenylglycines and Its Structure
  作者：Motohiro Akazome、Yukiko Yanagita、Ryo-ichi Sonobe、Katsuyuki Ogura

  DOI：10.1246/bcsj.70.2823

  日期：1997.11

  The crystallization of (R)-arylglycyl-(R)-phenylglycine (1, aryl = phenyl; 2, aryl = 1-naphthyl) in the presence of 1,2-dimethoxybenzene or its derivatives affords an inclusion compound. A single-crystal X-ray analysis has shown that, in a 1,2-dimethyoxybenzene inclusion compound, dipeptide molecules arrange in a sheet and the 1,2-dimethoxybenzene lies at the end in a void between the sheets by being

  (R)-芳基甘氨酰-(R)-苯基甘氨酸（1，芳基=苯基；2，芳基=1-萘基）在1,2-二甲氧基苯或其衍生物存在下的结晶得到包含化合物。单晶 X 射线分析表明，在 1,2-二甲氧基苯包合物中，二肽分子排列成片状，而 1,2-二甲氧基苯通过锚定在片状体之间的空隙中而位于末端片材上的氨氢通过三中心氢键。发现片材之间的距离根据客体 1,2-二甲氧基苯衍生物的长度而变化，就好像它们是支撑片材的柱子一样。
• A new system for molecular recognition: Highly specific inclusion of ()-isopropyl phenyl sulfoxide by solid ()-phenylglycyl-()-phenylglycine
  作者：Katsuyuki Ogura、Tohru Uchida、Makoto Noguchi、Masanori Minoguchi、Atsuko Murata、Makoto Fujita、Koreharu Ogata

  DOI：10.1016/s0040-4039(00)89057-7

  日期：1990.1
• OGURA, KATSUYUKI;UCHIDA, TOHRU;NOGUCHI, MAKOTO;MINOGUCHI, MASANORI;MURATA+, TETRAHEDRON LETT., 31,(1990) N3, C. 3331-3334
  作者：OGURA, KATSUYUKI、UCHIDA, TOHRU、NOGUCHI, MAKOTO、MINOGUCHI, MASANORI、MURATA+

  DOI：——

  日期：——
• BIEDERMANN, J.;ETSCHENBERG, E.;FRIEHE, H.;SCHEEF, W.;WINKELMANN, J.
  作者：BIEDERMANN, J.、ETSCHENBERG, E.、FRIEHE, H.、SCHEEF, W.、WINKELMANN, J.

  DOI：——

  日期：——
• Enantioselective Inclusion of Methyl Phenyl Sulfoxides and Benzyl Methyl Sulfoxides by (<i>R</i>)-Phenylglycyl-(<i>R</i>)-phenylglycine and the Crystal Structures of the Inclusion Cavities
  作者：Motohiro Akazome、Yuki Ueno、Haruko Ooiso、Katsuyuki Ogura

  DOI：10.1021/jo991051l

  日期：2000.1.1

  Crystalline (R)-phenylglycyl-(R)-phenylglycine [(R,R)-1] includes methyl phenyl sulfoxides (2 and 3) and benzyl methyl sulfoxides (4) with high enantioselectivity. The dipeptide exhibited different stereoselectivity depending on four structural isomers of methyl tolyl sulfoxide (C8H10OS): R for methyl 2-tolyl sulfoxide, S for methyl 3-tolyl sulfoxide, and racemic for methyl 4-tolyl sulfoxide. A structural isomer, benzyl methyl sulfoxide, was included in racemic form. Chlorophenyl methyl sulfoxides 3 (C7H7ClOS) with a similar volume showed the same enantioselectivity for their recognition. By single-crystal X-ray analyses of these inclusion compounds, it was elucidated that (R,R)-1 molecules self-assembled to form layer structures and included the sulfoxides between these layers and that the origin of the enantioselectivity based on chiral cavities was induced by conformation of the C-terminal phenyl group of the dipeptide. The relative position between the ammonio proton and the C-terminal phenyl group in one molecule of the dipeptide determined the stereochemistry of the methyl sulfinyl groups to be recognized. Various positional isomers of methyl xylyl sulfoxide having the formula of C9H12OS were subjected to the enantioselective inclusion by (R,R)-1 crystals and these results are also discussed.