(1S,2S)-(-)-2-氨基-1-环戊烷羧酸 | 64191-13-5

• 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: (1S,2S)-(-)-2-氨基-1-环戊烷羧酸
• 英文名称: (1S,2S)-2-amino-cyclopentanecarboxylic acid
• 英文别名: (1S,2S)-2-azaniumylcyclopentane-1-carboxylate
• CAS: 64191-13-5
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: JWYOAMOZLZXDER-WHFBIAKZSA-N

物化性质

• 熔点：
  146-147 °C(Solv: ethanol (64-17-5); ethyl acetate (141-78-6))
• 沸点：
  264.7±33.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)
• 溶解度：
  甲醇（微溶）、水（微溶）

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

安全信息

• 海关编码：
  2922499990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (1S,2S)-(-)-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 (1S,2S)-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：

  tert-butyl ((trans)-2-cyanocyclopentyl)carbamate 在 盐酸 作用下， 以85%的产率得到(1S,2S)-(-)-2-氨基-1-环戊烷羧酸
  参考文献：
  名称：

  新型硅烷取代的β-氨基酸的合成

  摘要：

  已经从简单的起始原料开发了非天然环状被硅烷取代的β-氨基酸的高效立体选择性合成方法。关键步骤是中间体氮丙啶与羧酸盐阴离子的聚砜合成子的亲核开环。官能团操纵和脱保护反应允许获得所需的反式β-氨基酸。

  DOI：

  10.1016/s0040-4039(02)01085-7

文献信息

• Radical cyclization in heterocycle synthesis. Part 13: Sulfanyl radical addition–cyclization of oxime ethers and hydrazones connected with alkenes for synthesis of cyclic β-amino acids
  作者：Okiko Miyata、Kanami Muroya、Tomoko Kobayashi、Rina Yamanaka、Seiko Kajisa、Junko Koide、Takeaki Naito

  DOI：10.1016/s0040-4020(02)00412-x

  日期：2002.5

  combination of sulfanyl radical addition–cyclization of the oxime ethers and hydrazones connected with alkenes and subsequent conversion of a phenylsulfanylmethyl group to a carboxyl group provides a novel method for the construction of the cyclic β-amino acids. Upon treatment with thiophenol in the presence of AIBN, the oxime ethers and hydrazones smoothly underwent sulfanyl radical addition-cyclization

  硫醚基自由基加成－肟醚和与烯烃连接的的环化反应以及随后苯硫烷基甲基到羧基的转化提供了一种构造环状β-氨基酸的新方法。在AIBN存在下用苯硫酚处理后，使肟醚和平稳地进行硫烷基自由基加成-环化反应，得到2-（苯基硫烷基甲基）环烷基胺。该方法已成功应用于2-氨基环戊烷羧酸和4-氨基-3-吡咯烷羧酸的实际合成。
• 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。
• 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。
• A Novel Preparation of 2-Aminocyclopentanecarboxamides
  作者：Péter Csomós、Gábor Bernáth、Ferenc Fülöp

  DOI：10.1007/s007060200077

  日期：2002.8.1

   Different syntheses of cis - and trans -2-aminocyclopentanecarboxamides were studied. A convenient and effective method was devised for the preparation of cis -2-aminocyclopentanecarboxamide derivatives starting from the readily available 6- tert -butoxycarbonyl-6-azabicyclo[3.2.0]heptan-7-one.

   研究了 顺式 和 反式 -2-氨基环戊烷羧酰胺的不同合成方法 。设计了一种方便有效的方法，从容易获得的6- 叔 丁氧羰基-6-氮杂双环[3.2.0]庚烷-7-一开始制备 顺 -2-氨基环戊烷甲酰胺衍生物 。
• Quasiracemate Crystal Structures of Magainin 2 Derivatives Support the Functional Significance of the Phenylalanine Zipper Motif
  作者：Zvi Hayouka、Nicole C. Thomas、David E. Mortenson、Kenneth A. Satyshur、Bernard Weisblum、Katrina T. Forest、Samuel H. Gellman

  DOI：10.1021/jacs.5b07206

  日期：2015.9.23

  Quasiracemic crystallography has been used to explore the significance of homochiral and heterochiral associations in a set of host-defense peptide derivatives. The previously reported racemic crystal structure of a magainin 2 derivative displayed a homochiral antiparallel dimer association featuring a "phenylalanine zipper" notable for the dual roles of phenylalanines in mediating dimerization and

  准消旋晶体学已被用来探索一组宿主-防御肽衍生物中同手性和异手性缔合的意义。先前报道的magainin 2衍生物的外消旋晶体结构显示出纯手性反平行二聚体缔合，其特征在于苯丙氨酸在介导二聚化和形成暴露的疏水性条带中的双重作用。这种基序也出现在两种新的准消旋体晶体中，它们含有 d 型 magainin 2 衍生物以及一种 L 肽，其中一个 Ala 已被 β 氨基酸残基取代。这种结构趋势支持了 Phe 拉链基序具有功能意义的假设。