(1R,2R)-(-)-2-氨基-1-环戊烷羧酸 | 136315-77-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 其他氨基酸衍生物
• 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
• 中文名称: (1R,2R)-(-)-2-氨基-1-环戊烷羧酸
• 英文名称: trans-2-Amino-cyclopentan-carbonsaeure
• 英文别名: (1R,2R)-2-azaniumylcyclopentane-1-carboxylate
• CAS: 136315-77-0
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: JWYOAMOZLZXDER-RFZPGFLSSA-N

物化性质

• 沸点：
  264.7±33.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2R)-(-)-2-氨基-1-环戊烷羧酸 在 钯 氯化亚砜 、 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 、 N,N-二甲基甲酰胺 为溶剂， -30.0~25.0 ℃ 、101.33 kPa 条件下， 反应 31.0h， 生成 (1R,2R)-L-aspartyl-trans-2-aminocyclopentanecarboxylic acid methyl ester
  参考文献：
  名称：

  Probing a molecular model of taste utilizing peptidomimetic stereoisomers of 2-aminocyclopentanecarboxylic acid methyl ester

  摘要：

  On the basis of the preferred conformations of L-aspartyl dipeptide derivatives containing alpha-amino acids at the second position and their retro-inverso analogues deduced by a combination of X-ray crystallography, H-1 NMR spectroscopy, and molecular mechanics calculations, we have proposed a model describing the molecular array required for the sweet taste. The conformation of a sweet molecule is described as possessing an "L shape", with the AH (proton donor) and B (proton acceptor) zwitterionic ring of the aspartyl moiety forming the stem, and the hydrophobic group X forming the base of the "L". Planarity of the molecule in the x and y dimensions is critical for sweet taste. Substantial deviation from this plane into negative z dimension is correlated with bitter taste while other deviations lead to tasteless molecules. To examine the model, the preferred conformations for a series of L-aspartyl dipeptides containing a 2-aminocyclopentanecarboxylic acid (2-Ac5c) residue at the second position were calculated using molecular mechanics. The peptidomimetic 2-Ac5c residue is a beta-amino acid with two chiral centers, resulting in four isomers [trans-(1S,2S)-2-Ac5c, trans-(1R,2R)-2-Ac5c, cis-(1R,2S)-2-Ac5c, and cis-(1S,2R)-2-Ac5c]. Two stereoisomers, L-aspartyl-trans-(1R,2R)-2-aminocyclopentanecarboxylic acid methyl ester [Asp-trans-(1R,2R)-2-Ac5c-OMe] and L-aspartyl-cis-(1S,2R)-2-aminocyclopentanecarboxylic acid methyl ester [Asp-cis-(1S,2R)-2-Ac5c-OMe], prefer the L-shape conformations and are thus predicted to be sweet. For L-aspartyl-trans-(1S,2S)-2-aminocyclopentanecarboxylic acid methyl ester [Asp-trans-(1S,2S)-2-Ac5c-OMe], the methyl ester group projects behind the stem of the L shape, producing a large negative z component and is predicted to exhibit a bitter taste. The calculations predict that L-aspartyl-cis-(1R,2S)-2-aminocyclopentanecarboxylic acid methyl ester [Asp-cis-(1R,2S)-2-Ac5c-OMe] will be tasteless. In this investigation, in addition to the calculations, we report the synthesis and experimental conformational analysis of the four stereoisomers of Asp-2-Ac5c-OMe. The absolute configurations of the 2-Ac5c residues were assigned by X-ray diffraction studies and by correlating optical rotation and enantiomeric excess values. These studies fully confirm our configurational assignments of the stereoisomers of Asp-2-Ac5c-OMe. Thus, the structure-taste relationships observed for the new class of L-aspartyl taste ligands containing the 2-Ac5c beta-amino acid methyl esters in the second position agree with and strengthen our model for the sweet and bitter taste responses.

  DOI：

  10.1021/jo00023a033
• 作为产物：
  描述：

  -(R)-(+)-α-methylbenzylamine 在 盐酸 、 三氟乙酸 作用下， 反应 10.0h， 生成 (1R,2R)-(-)-2-氨基-1-环戊烷羧酸
  参考文献：
  名称：

  Probing a molecular model of taste utilizing peptidomimetic stereoisomers of 2-aminocyclopentanecarboxylic acid methyl ester

  摘要：

  On the basis of the preferred conformations of L-aspartyl dipeptide derivatives containing alpha-amino acids at the second position and their retro-inverso analogues deduced by a combination of X-ray crystallography, H-1 NMR spectroscopy, and molecular mechanics calculations, we have proposed a model describing the molecular array required for the sweet taste. The conformation of a sweet molecule is described as possessing an "L shape", with the AH (proton donor) and B (proton acceptor) zwitterionic ring of the aspartyl moiety forming the stem, and the hydrophobic group X forming the base of the "L". Planarity of the molecule in the x and y dimensions is critical for sweet taste. Substantial deviation from this plane into negative z dimension is correlated with bitter taste while other deviations lead to tasteless molecules. To examine the model, the preferred conformations for a series of L-aspartyl dipeptides containing a 2-aminocyclopentanecarboxylic acid (2-Ac5c) residue at the second position were calculated using molecular mechanics. The peptidomimetic 2-Ac5c residue is a beta-amino acid with two chiral centers, resulting in four isomers [trans-(1S,2S)-2-Ac5c, trans-(1R,2R)-2-Ac5c, cis-(1R,2S)-2-Ac5c, and cis-(1S,2R)-2-Ac5c]. Two stereoisomers, L-aspartyl-trans-(1R,2R)-2-aminocyclopentanecarboxylic acid methyl ester [Asp-trans-(1R,2R)-2-Ac5c-OMe] and L-aspartyl-cis-(1S,2R)-2-aminocyclopentanecarboxylic acid methyl ester [Asp-cis-(1S,2R)-2-Ac5c-OMe], prefer the L-shape conformations and are thus predicted to be sweet. For L-aspartyl-trans-(1S,2S)-2-aminocyclopentanecarboxylic acid methyl ester [Asp-trans-(1S,2S)-2-Ac5c-OMe], the methyl ester group projects behind the stem of the L shape, producing a large negative z component and is predicted to exhibit a bitter taste. The calculations predict that L-aspartyl-cis-(1R,2S)-2-aminocyclopentanecarboxylic acid methyl ester [Asp-cis-(1R,2S)-2-Ac5c-OMe] will be tasteless. In this investigation, in addition to the calculations, we report the synthesis and experimental conformational analysis of the four stereoisomers of Asp-2-Ac5c-OMe. The absolute configurations of the 2-Ac5c residues were assigned by X-ray diffraction studies and by correlating optical rotation and enantiomeric excess values. These studies fully confirm our configurational assignments of the stereoisomers of Asp-2-Ac5c-OMe. Thus, the structure-taste relationships observed for the new class of L-aspartyl taste ligands containing the 2-Ac5c beta-amino acid methyl esters in the second position agree with and strengthen our model for the sweet and bitter taste responses.

  DOI：

  10.1021/jo00023a033

文献信息

• Novel 6-fused heteroaryldihydropyrimidines for the treatment and prophylaxis of hepatitis B virus infection
  申请人：HOFFMANN-LA ROCHE INC.

  公开号：US20150252057A1

  公开（公告）日：2015-09-10

  The invention provides novel compounds having the general formula: wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , X, Y, W and n are as described herein, compositions including the compounds and methods of using the compounds.

  这项发明提供了具有以下一般式的新化合物： 其中R1、R2、R3、R4、R5、R6、X、Y、W和n如本文所述，包括这些化合物的组合物以及使用这些化合物的方法。
• [EN] PD-1/PD-L1 INHIBITORS<br/>[FR] INHIBITEURS PD-1/PD-L1
  申请人：GILEAD SCIENCES INC

  公开号：WO2018195321A1

  公开（公告）日：2018-10-25

  Compounds according to formula (I), methods of using said compounds singly or in combination with additional agents and compositions of said compounds for the treatment of cancer are disclosed.

  根据公式（I）制备的化合物，以及使用这些化合物单独或与其他药剂结合的方法，以及用于治疗癌症的这些化合物的组合物被披露。
• PEPTIDES AND PEPTIDOMIMETIC COMPOUNDS, THE MANUFACTURING THEREOF AS WELL AS THEIR USE FOR PREPARING A THERAPEUTICALLY AND/OR PREVENTIVELY ACTIVE PHARMACEUTICAL COMPOSITION
  申请人：PETZELBAUER Peter

  公开号：US20100081787A1

  公开（公告）日：2010-04-01

  Peptides, peptidomimetics and derivatives thereof of the general formula I: H 2 N-GHRPX 1 - β -X 4 X 5 X 6 X 7 X 8 X 9 X 10 -X 11 (I), in which X 1 -X 10 denote one of the 20 genetically coded amino acids, wherein X 8 , X 9 and X 10 may also denote a single chemical bond; X 11 denotes OR 1 in which R 1 equals hydrogen or (C 1 -C 10 ) alkyl NR 2 R 3 with R 2 and R 3 are equal or different and denote hydrogen, (C 1 -C 10 ) alkyl, or a residue —W-PEG 5-60K , in which the PEG residue is attached via a suitable spacer W to the N-atom, or a residue NH—Y-Z-PEG 5-60K , in which Y denotes a chemical bond or a genetically coded amino acids from the group S, C, K or R and Z denotes a spacer, via which a polyethylene glycol (PEG)-residue can be attached, and their physiologically acceptable salts, and β denotes an amino acid, or a peptidomimetic element, which induces a bend or turn in the peptide backbone.

  通用公式I：H2N-GHRPX1-β-X4X5X6X7X8X9X10-X11(I)中的肽、肽类似物和衍生物，其中X1-X10表示20种遗传编码的氨基酸之一，其中X8、X9和X10也可以表示单一化学键；X11表示OR1，其中R1等于氢或(C1-C10)烷基NR2R3，其中R2和R3相同或不同，表示氢、(C1-C10)烷基，或者残基—W-PEG5-60K，其中PEG残基通过适当的间隔物W连接到N-原子，或者残基NH—Y-Z-PEG5-60K，其中Y表示化学键或来自S、C、K或R组的遗传编码氨基酸，Z表示间隔物，通过该间隔物可以连接聚乙二醇（PEG）残基，并且它们的生理上可接受的盐，β表示氨基酸或诱导肽骨架中弯曲或转弯的肽类或肽类似元素。
• SURFACE-MODIFIED POLYMERIC SUBSTRATES GRAFTED WITH A PROPERTIES-IMPARTING COMPOUND USING CLIP CHEMISTRY
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：US20190247551A1

  公开（公告）日：2019-08-15

  The present invention relates to an efficient method for grafting a properties-imparting compound onto a polymeric substrate containing carbon-hydrogen (C—H) bonds using clip chemistry. The method of the invention includes coating the substrate with the properties-imparting compound and irradiating it with a reactive light source, and repeating this sequence at least once. The present invention further relates to surface-modified polymeric substrates grafted with a properties-imparting compound, in particular obtained with the method of the invention, medical devices comprising same, and non-medical of said surface-modified polymeric substrates.

  本发明涉及一种将赋予性质的化合物嫁接到含有碳氢（C—H）键的聚合物基底的高效方法，使用剪切化学。该发明的方法包括用赋予性质的化合物涂覆基底，并用反应性光源照射它，至少重复这个序列一次。本发明还涉及经过赋予性质的化合物嫁接的表面改性聚合物基底，特别是使用本发明方法获得的，包括同样的医疗设备，以及非医疗用途的表面改性聚合物基底。
• Age Inhibitors
  申请人：Potier Pierre

  公开号：US20080249030A1

  公开（公告）日：2008-10-09

  The invention relates to a compound having general formula I, wherein: X represents CH 2 , C═O, C═S or CHOH, X represents CH 2 , C═O, C═S or CHOH, R 1 represents an amino acid which is optionally substituted by one or more halogen atoms, preferably fluorine, or by one or more CF 3 groups and n=0.1 or 2, or X represents CH 2 , C═O, C═S, CHOH, R 1 represents a peptide containing two amino acids, each amino acid being optionally substituted by one or more halogen atoms, preferably fluorine, or by one or more CF 3 groups and n=0 or 1, or XR 1 represent PO 3 H or SO 3 H and n=0.1 or 2; R 2 represents H, XR 1 , an alkyl group at C 1 -C 6 , an aralkyl group at C 1 -C 6 or an aryl group, whereby the alkyl, aralkyl and aryl groups can be substituted by an amine NH 2 , a carboxylic group COOH, one or more halogen atoms, preferably fluorine, or one or more CF 3 groups; or the pharmaceutically-acceptable addition salts, isomers, enantiomers and diastereoisomers of said compound, mixtures thereof, and pharmaceutical or cosmetic compositions comprising same and the use thereof as an AGE-inhibitor drug that traps reactive carbonyl compounds.

  该发明涉及一种具有一般式I的化合物，其中：X代表CH2、C═O、C═S或CHOH，X代表CH2、C═O、C═S或CHOH，R1代表一种氨基酸，该氨基酸可以选择性地被一个或多个卤素原子（优选为氟）或一个或多个CF3基团取代，n=0.1或2，或者X代表CH2、C═O、C═S、CHOH，R1代表含有两个氨基酸的肽，每个氨基酸可以选择性地被一个或多个卤素原子（优选为氟）或一个或多个CF3基团取代，n=0或1，或者XR1代表PO3H或SO3H，n=0.1或2；R2代表H、XR1、C1-C6的烷基、C1-C6的芳基烷基或芳基，其中烷基、芳基烷基和芳基可以被氨基NH2、羧基COOH、一个或多个卤素原子（优选为氟）或一个或多个CF3基团取代；或者所述化合物的药学上可接受的加合盐、异构体、对映体和二对映异构体，其混合物，以及包含其的制药或化妆品组合物及其作为捕捉反应性羰基化合物的AGE抑制剂药物的用途。

表征谱图