(1S,2r)-Fmoc-2-氨基环己烷 羧酸 | 194471-85-7

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 环羧酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: (1S,2r)-Fmoc-2-氨基环己烷 羧酸
• 中文别名: (1S,2R)-FMOC-氨基环己烷羧酸；(1S,2r)-Fmoc-2-氨基环己烷羧酸
• 英文名称: Fmoc-cis-2-aminocyclohexane carboxylic acid
• 英文别名: (1S,2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)cyclohexane-1-carboxylic acid
• CAS: 194471-85-7；430460-38-1
• 化学式: C₂₂H₂₃NO₄
• 分子量: 365.429
• InChiKey: NZMNDTGOODAUNI-AZUAARDMSA-N

物化性质

• 沸点：
  596.9±39.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• WGK Germany：
  3
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (1S,2r)-Fmoc-2-氨基环己烷 羧酸 、 (1R,2S)-2-((((9H-芴-9-基)甲氧基)羰基)环己烷甲酸 在 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 3.0h， 以43%的产率得到
  参考文献：
  名称：

  Building β-Peptide H10/12 Foldamer Helices with Six-Membered Cyclic Side-Chains: Fine-Tuning of Folding and Self-Assembly

  摘要：

  The ability of the beta-peptidic H10/12 helix to tolerate side-chains containing six-membered alicyclic rings was studied. cis-2-Aminocyclohex-3-ene carboxylic acid (cis-ACHEC) res dues afforded H10/12 helix formation with alternating backbone configuration. Conformational polymorphism was observed for the alternating cis-ACHC hexamer, where chemical exchange takes place between the major left-handed H10/12 helix and a minor folded conformation. The hydrophobically driven self-assembly was achieved for the cis-ACHC-containing helix which was observed as vesicles similar to 100 nm in diameter.

  DOI：

  10.1021/ol102494m
• 作为产物：
  描述：

  (1S,6R)-8-oxo-7-azabicyclo[4.2.0]octane-7-sulfonyl chloride 在 盐酸 、 水 、 potassium hydrogencarbonate 、 sodium hydroxide 、 sodium sulfite 作用下， 以 水 为溶剂， 反应 14.0h， 生成 (1S,2r)-Fmoc-2-氨基环己烷 羧酸
  参考文献：
  名称：

  Large-Scale Syntheses of FMOC-Protected Non-Proteogenic Amino Acids:  Useful Building Blocks for Combinatorial Libraries

  摘要：

  Convenient and reliable large-scale procedures for the protection of various amino acids with N-(9-fluorenyimethoxycarbonyl)oxysuccinimide (FMOC-OSu) are described. Commercially available 4-aminomethylbenzoic acid and trans-4-(aminomethyl)cyclohexanecarboxylic acid were converted into their corresponding FMOC-derivatives in excellent yields without the need for an extractive workup. In addition, FMOC-cis-beta -amino acids were also prepared, employing a [2 + 2]-cycloaddition strategy between a cyclic olefin and N-chlorosulfonyl isocyanate (CSI). The resulting N-chlorosulfonyl fl-lactams were reduced to the parent beta -lactams with sodium sulfite and then converted to the cis-fi-amino acid hydrochlorides by exposure to aqueous hydrochloric acid. The resulting cis-fi-amino acids were converted to their FMOC-derivatives under conditions similar to those developed for the commercially available amino acids. Differences in the conditions employed between these beta -amino acids and the commercial derivatives were observed, primarily in the nature of the base required for the reaction. A possible rationale for the differences in behavior is described. These FMOC-amino acid derivatives are valuable intermediates for the solid-phase synthesis of combinatorial libraries.

  DOI：

  10.1021/op010204f

文献信息

• Configuration-Dependent Medium-Sized Ring Formation: Chiral Molecular Framework with Three-Dimensional Architecture
  作者：Naděžda Cankařová、Agustina La Venia、Soňa Krajčovičová、Viktor Krchňák

  DOI：10.1021/acs.joc.8b02465

  日期：2019.1.18

  formation via a tandem cyclic N-acyliminium nucleophilic addition reaction. Cyclization of the acyclic precursor prepared on a solid phase using l-Ser and a racemic mixture of Fmoc-trans-2-aminocyclohexanecarboxylic acid predominantly yielded the cyclic diastereomer with the (1R,2R)-2-aminocyclohexane moiety rather than the tricyclic diastereomer from the (1S,2S)-enantiomer. In contrast, the model compound

  该报告描述了通过串联环状N-酰基亚胺基亲核加成反应的构型依赖性[6 + 8 + 5]稠合环的形成。使用1- Ser和Fmoc-反式-2-氨基环己烷羧酸的外消旋混合物在固相上制备的无环前体的环化反应主要产生的是具有（1 R，2 R）-2-氨基环己烷部分而不是三环的环状非对映异构体（1 S，2 S）-对映体的非对映异构体。相反，用d- Ser制备的模型化合物主要以（1 S，2 S）-2-氨基环己烷羧酸底物。环化的结果不受树脂类型，间隔基或N取代基的影响。[6 + 7 + 5]稠环系统的类似合成产生了不可分离的非对映异构体，比例为1：0.6。
• Structural properties of cyclic peptides containing cis- or trans-2-aminocyclohexane carboxylic acidElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/ob/b3/b312432k/
  作者：Ulf Strijowski、Norbert Sewald

  DOI：10.1039/b312432k

  日期：——

  A series of cyclic peptides containing either cis- or trans-2-aminocyclohexane carboxylic acid as mimics for L-proline has been synthesized and their structural properties have been investigated using NMR and MD methods.

  合成了一系列包含顺式或反式-2-氨基环己烷羧酸作为L-脯氨酸模拟物的环状肽，并使用NMR和MD方法研究了其结构性质。
• Peptides comprising non-natural amino acids and methods of making and using the same
  申请人：Longevity Biotech, Inc.

  公开号：US10543255B2

  公开（公告）日：2020-01-28

  This invention relates to novel compositions comprising analogs of naturally occurring polypeptides, wherein the analog comprises an α-amino acid and at least one β-amino acid. Administration of the compositions may be used for effecting treatment or prevention of a plurality of disease states caused by dysfunctional biochemical or biological pathways. The compositions and methods of this invention are particularly useful to identify novel therapeutic modulators of in-vivo receptor activity with extended half-lives and relevant bioactivity as compared to the naturally translated polypeptides upon which the analogs are derived.

  本发明涉及由天然多肽类似物组成的新型组合物，其中类似物包括一种α-氨基酸和至少一种β-氨基酸。给药组合物可用于治疗或预防由生化或生物途径功能障碍引起的多种疾病状态。本发明的组合物和方法特别适用于鉴定体内受体活性的新型治疗调节剂，与天然翻译的多肽相比，本发明的类似物具有更长的半衰期和相关的生物活性。
• Highly active polypeptides and methods of making and using the same
  申请人：Longevity Biotech, Inc.

  公开号：US10772934B2

  公开（公告）日：2020-09-15

  This invention relates to novel compositions comprising analogs of naturally occurring polypeptides, wherein the analog comprises an α-amino acid and at least one β-amino acid. Administration of the compositions may be used for effecting treatment or prevention of a plurality of disease states caused by dysfunctional biochemical or biological pathways. The compositions and methods of this invention are particularly useful to identify novel therapeutic modulators of in-vivo receptor activity with extended half-lives and relevant bioactivity as compared to the naturally translated polypeptides upon which the analogs are derived.

  本发明涉及由天然多肽类似物组成的新型组合物，其中类似物包括一种α-氨基酸和至少一种β-氨基酸。给药组合物可用于治疗或预防由生化或生物途径功能障碍引起的多种疾病状态。本发明的组合物和方法特别适用于鉴定体内受体活性的新型治疗调节剂，与天然翻译的多肽相比，本发明的类似物具有更长的半衰期和相关的生物活性。
• Marastoni, Mauro; Guerrini, Remo; Balboni, Gianfranco, Arzneimittel-Forschung/Drug Research, 1999, vol. 49, # 1, p. 6 - 12
  作者：Marastoni, Mauro、Guerrini, Remo、Balboni, Gianfranco、Salvadori, Severo、Fantin, Giancarlo、Fogagnolo, Marco、Lazarus, Lawrence H.、Tomatis, Roberto

  DOI：——

  日期：——