(+)-(1R,2S)-allocoronamic acid | 65878-53-7

• 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: (+)-(1R,2S)-allocoronamic acid
• 英文别名: (+)-allo-Coronamic Acid；(1R,2S)-1-amino-2-ethylcyclopropanecarboxylic acid；(1R,2S)-1-amino-2-ethylcyclopropane-1-carboxylic acid
• CAS: 65878-53-7
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: RLHIWMRQDUCBDO-UJURSFKZSA-N

物化性质

• 沸点：
  238.1±23.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  9
• 可旋转键数：
  2
• 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,2S)-allocoronamic acid 生成 丁烯
  参考文献：
  名称：

  关于乙烯的生物合成。使用修饰的底物确定立体化学过程

  摘要：

  据报道苹果组织将一系列特定的2-烷基化的3-氘代的-1-氨基环戊羧酸转化为顺式和反式-1-氘代烷-1-烯的混合物。结果符合环丙烷开环的逐步酶促机理，其中立体化学平衡比随后的键断裂过程快。

  DOI：

  10.1039/c39850001496
• 作为产物：
  描述：

  (1S,2R)-1-Amino-2-ethyl-cyclopropanecarboxylic acid methyl ester; hydrochloride 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 作用下， 反应 18.0h， 生成 (+)-(1R,2S)-allocoronamic acid
  参考文献：
  名称：

  外消旋2-烷基-1-氨基环丙烷-1-羧酸的拆分

  摘要：

  为（1外消旋修饰的分辨率实用程序，2 ） -和（1 ，2 ）-1-氨基-2-乙基环-1-羧酸，（1 ，2 ） -和（1 ，2 ）-1-氨基-2-甲基环丙烷-1-羧酸，以及（1 ，2 ） -和（1 ，2 ）-1-氨基-2-甲基环丙烷-1-羧酸，被描述; X射线晶体学方法证实其结构为，和。

  DOI：

  10.1016/s0040-4039(00)61918-4

文献信息

• Diazotization of 1-aminocyclopropanecarboxylic acid. Solution chemistry of oxaspiropentanone
  作者：Michael C. Pirrung、William L. Brown

  DOI：10.1021/ja00173a032

  日期：1990.8

  La 1-oxaspiro [2,2] pentan-2-one est un intermediaire dans la diazotation de l'acide 1-aminocyclopropanecarboxylique

  La 1-oxaspiro [2,2] pentan-2-one est un intermediaire dans la diazotation de l'acide 1-aminocyclopropanecarboxylique
• METHOD FOR PRODUCING SOLID AMINO ACID
  申请人：Kaneka Corporation

  公开号：EP2810933A1

  公开（公告）日：2014-12-10

  The problem to be solved by the present invention is to ea sily and efficiently produce an amino acid having 2 to 7 carbon atoms as a high-purity solid without complicated operation, whic h is useful as a synthetic intermediate for medicines or agroche micals. The present invention is characterized in comprising a ste p of precipitating solid amino acid with high purity. In the pr esent invention, the by-produced salt composed of the sulfonic a cid and the amine was removed to the mother liquor by reacting a n amine with a sulfonic acid salt of amino acid in an aprotic pol ar solvent, or by reacting a sulfonic acid with an amine salt of amino acid in an aprotic polar solvent. The sulfonic acid salt of amino acid, for example, may be produced by reacting a N-(tert-butoxycarbonyl) amino acid with a sulfonic acid, or by reacting an amino acid tert-butyl ester we th a sulfonic acid.

  本发明要解决的问题是在不进行复杂操作的情况下，轻松高效地生产出一种具有 2 至 7 个碳原子的高纯度固体氨基酸，该氨基酸可用作药物或农用化学品的合成中间体。 本发明的特征在于包括一种沉淀高纯度固体氨基酸的方法。在本发明中，通过使胺与氨基酸的磺酸盐在非沸腾极性溶剂中反应，或使磺酸与氨基酸的胺盐在非沸腾极性溶剂中反应，将由磺酸和胺组成的副产盐除去到母液中。 例如，氨基酸的磺酸盐可通过 N-（叔丁氧羰基）氨基酸与磺酸反应，或通过氨基酸叔丁酯与磺酸反应制得。
• METHOD FOR PRODUCING HYDROPHOBIC PEPTIDE
  申请人：Kaneka Corporation

  公开号：EP3199540A1

  公开（公告）日：2017-08-02

  An object of the present invention is to provide a producing method: that allows any hydrophobic peptide to be used as an object to be purified, in hydrophilizing a hydrophobic peptide, synthesized by solid-phase peptide synthesis, with a hydrophilic unit and purifying the hydrophobic peptide by HPLC, regardless of the type of the amino acid residue at the N-terminus; that allows the hydrophilic unit to be flexibly selected in accordance with the type of the hydrophobic peptide; and that is excellent in versatility. The present invention is characterized by a method for producing a purified peptide from a supported crude peptide including a support and a first peptide chain bonded to the support at a C-terminus, the method comprising: a hydrophilization step A of introducing a linker and a hydrophilic unit to an amino group of the supported crude peptide in this order stepwise or at a single step to obtain a support-free hydrophilized peptide; a support cleavage step B of cleaving a bond between the first peptide chain and the support at any stage before bonding the linker to the supported crude peptide until the hydrophilized peptide is obtained, or after a supported hydrophilized peptide is obtained; a chromatographic purification step of treating the support-free hydrophilized peptide obtained by the hydrophilization step A and the support cleavage step B, by liquid chromatography; and a linker cleavage step of cleaving a bond between the linker and the first peptide chain included in the chromatographically-purified support-free hydrophilized peptide, by chemical treatment.

  本发明的目的是提供一种生产方法：该方法可以将任何疏水性多肽作为纯化对象，在用亲水单元亲水固相多肽合成法合成的疏水性多肽时，通过高效液相色谱法纯化疏水性多肽，而不考虑N端氨基酸残基的类型；该方法可以根据疏水性多肽的类型灵活选择亲水单元；该方法具有优异的通用性。 本发明的特征在于一种从支持粗肽生产纯化肽的方法，该粗肽包括支持物和在 C 端与支持物键合的第一肽链，该方法包括： 亲水化步骤 A，按此顺序逐步或单步将连接体和亲水单元引入到支撑粗肽的氨基上，以获得无支撑的亲水化肽； 支持物裂解步骤B，在将连接物与支持物粗肽结合之前的任何阶段裂解第一肽链与支持物之间的键，直到获得亲水肽，或在获得支持物亲水肽之后； 色谱纯化步骤：用液相色谱法处理通过亲水化步骤 A 和支持物裂解步骤 B 获得的无支持物亲水化肽；以及 连接体裂解步骤，通过化学处理裂解连接体与色谱纯化的无支撑亲水肽中的第一肽链之间的键。
• Asymmetric syntheses of 1-amino-2-phenyl(alkyl)cyclopropanecarboxylic acids by diastereoselective cyclopropanation of highly functionalized monochiral olefines
  作者：Carmen Alcaraz、Ma Dolores Fernández、Ma Pilar de Frutos、Joseé L. Marco、Manuel Bernabé、Concepción Foces-Foces、Félix H. Cano

  DOI：10.1016/s0040-4020(01)89550-8

  日期：1994.1

  Monochiral alpha-benzamidocinnamic esters of N-methylephedrine or mandelic derivatives and benzylidene or alkylidene diketopiperazines, all obtained from oxazolones, react with diazomethane to give moderate to high diastereomeric excess (d.e) of pyrazoline derivatives which after photolysis and acid hydrolysis of the resulting cyclopropyl compounds, gave (1R,2R)-, (1S,2S)- or (1S,2R)-1-amino-2-phenyl(alkyl)cyclopropanecarboxylic acids. The enantiomerically pure dipeptide of the (1R,2R) enantiomer with S-proline was also obtained by selective cleavage of the diketopiperazine moiety. The structure of all compounds has been assessed by NMR studies and by X-ray crystallography analysis of an intermediate spiroderivative.
• Enantioselective synthesis of (+)-(1R,2S)-allocoronamic acid
  作者：Carmen Alcaraz、Angela Herrero、José L. Marco、Eldiberto Fernández-Alvarez、Manuel Bernabé

  DOI：10.1016/s0040-4039(00)61159-0

  日期：1992.9

  The asymmetric synthesis of (+)-(1R,2S)-allocoronamic acid is reported. Diazomethane addition to (Z)-N-(tert-butoxycarbonyl)ethyldehydroalanyl-L-prolin-anhydride, easily prepared from (Z)-2-phenyl-4-propylidene-5(4H)-oxazolone and L-proline, gave in high diastereomeric excess the corresponding spiropyrazoline, which was transformed, on photolysis and acid hydrolysis of the resulting spirocyclopropane, into (+)-(1R,2S)-1-amino-2-ethyl-cyclopropanecarboxylic acid.