(3R,4S)-1-(tert-butoxycarbonyl)-4-(((R)-1-phenylethyl)amino)pyrrolidine-3-carboxylic acid | 388109-45-3

• 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: (3R,4S)-1-(tert-butoxycarbonyl)-4-(((R)-1-phenylethyl)amino)pyrrolidine-3-carboxylic acid
• 英文别名: (3R,4S)-4-[(R)-1-phenyl-ethylamino]-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester；(3S,4R)-1-BOC--4-((S)-1-phenylethylamino)pyrrolidine-3-carboxylic acid；(3R,4S)-1-[(2-methylpropan-2-yl)oxycarbonyl]-4-[[(1R)-1-phenylethyl]amino]pyrrolidine-3-carboxylic acid
• CAS: 388109-45-3
• 化学式: C₁₈H₂₆N₂O₄
• 分子量: 334.415
• InChiKey: OEEAWANOYFHITM-BPLDGKMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S)-1-(tert-butoxycarbonyl)-4-(((R)-1-phenylethyl)amino)pyrrolidine-3-carboxylic acid 在 palladium on activated charcoal 、 氢气 、 碳酸氢钠 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 0.5h， 生成 (3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester
  参考文献：
  名称：

  3-Aminopyrrolidine-4-carboxylic acid as versatile handle for internal labeling of pyrrolidinyl PNA

  摘要：

  Conformationally restricted pyrrolidinyl PNAs with an alpha/beta-dipeptide backbone consisting of a nucleobase-modified proline and a cyclic five-membered amino acid spacer such as (1S,2S)-2-aminocyclopentanecarboxylic acid (ACPC) (acpcPNA) can form very stable hybrids with DNA with high Watson-Crick base pairing specificity. This work aims to explore the effect of incorporating 3-aminopyrrolidine-4-carboxylic acid (APC), which is isosteric to the ACPC spacer, into the acpcPNA. It is expected that the modification should not negatively affect the DNA binding properties, and that the additional nitrogen atom in the APC should provide a handle for internal modification. Orthogonally-protected (N-3-Fmoc/N-1-Boc and N-3-Fmoc/N-1-Tfa) APC monomers have been successfully synthesized and incorporated into the acpcPNA by Fmoc-solid-phase peptide synthesis. T-m, UV and CD spectroscopy confirmed that the (3R,4S)-APC could substitute the (1S,2S)-ACPC spacer in the acpcPNA with only slightly decreasing the stability of the hybrids formed between the modified acpc/apcPNA and DNA. In contrast, the (3S,4R) enantiomer of APC caused substantial destabilization of the hybrids. Furthermore, a successful on-solid-support internal labeling of the acpc/apcPNA via amide bond formation between pyrene-1-carboxylic acid or 4-(pyrene-1-yl) butyric acid and the pyrrolidine nitrogen atom of the APC spacer has been demonstrated. Fluorescence properties of the pyrene-labeled acpc/apcPNAs are sensitive to their hybridization states and can readily distinguish between complementary and single-mismatched DNA targets. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.079
• 作为产物：
  描述：

  N-BOC-4-氧代-3-吡咯烷甲酸乙酯 在 lithium hydroxide monohydrate 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 36.0h， 生成 (3R,4S)-1-(tert-butoxycarbonyl)-4-(((R)-1-phenylethyl)amino)pyrrolidine-3-carboxylic acid
  参考文献：
  名称：

  [EN] TLR2 MODULATOR COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF
  [FR] COMPOSÉS MODULATEURS DE TLR2, COMPOSITIONS PHARMACEUTIQUES ET LEURS UTILISATIONS

  摘要：

  本公开涉及调节Toll样受体（TLR）蛋白活性的化合物，包括激动剂或激活剂、部分激动剂和拮抗剂。特别感兴趣的是调节TLR2活性的化合物，以及使用这些化合物治疗与TLR2通路相关的癌症和其他疾病的方法。

  公开号：

  WO2021242923A1

文献信息

• N-ureidoheterocycloalkyl-piperidines as modulators of chemokine receptor activity
  申请人：——

  公开号：US20030032654A1

  公开（公告）日：2003-02-13

  The present application describes modulators of CCR3 of formula (I): 1 or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.

  本申请描述了CCR3的调节剂，其化学公式为(I)： 1 或其药用可接受的盐形式，用于预防哮喘和其他过敏性疾患。
• [EN] TLR2 MODULATOR COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF<br/>[FR] COMPOSÉS MODULATEURS DE TLR2, COMPOSITIONS PHARMACEUTIQUES ET LEURS UTILISATIONS
  申请人：AXIAL THERAPEUTICS INC

  公开号：WO2021242923A1

  公开（公告）日：2021-12-02

  The present disclosure relates to compounds which modulate the activity of Toll-like receptor (TLR) proteins, including agonists or activators, partial agonists, and antagonists. Of particular interest of compounds that modulate the activity of TLR2, as well as methods of using such compounds to treat cancer and other disorders associated with a TLR2 pathway.

  本公开涉及调节Toll样受体（TLR）蛋白活性的化合物，包括激动剂或激活剂、部分激动剂和拮抗剂。特别感兴趣的是调节TLR2活性的化合物，以及使用这些化合物治疗与TLR2通路相关的癌症和其他疾病的方法。
• BETA-AMINO ACIDS
  申请人：Gellman Samuel H.

  公开号：US20130023644A1

  公开（公告）日：2013-01-24

  Disclosed are β-amino acid monomers containing cylcoalkyl, cycloalkenyl, and heterocylic substituents which encompass the α and β carbons of the peptide backbone and β-polypeptides made from such monomers. Method of generating combinatorial libraries of polypeptides containing the β-peptide residues and libraries formed thereby are disclosed.

  本发明公开了含有环烷基，环烯基和杂环基取代基的β-氨基酸单体，这些取代基包括多肽骨架的α和β碳，以及由这些单体制成的β-多肽。本发明还公开了生成含有β-肽残基的多肽组合库的方法以及由此形成的库。
• An Efficient Route to Either Enantiomer of Orthogonally Protected <i>trans</i>-3-Aminopyrrolidine-4-carboxylic Acid
  作者：Hee-Seung Lee、Paul R. LePlae、Emilie A. Porter、Samuel H. Gellman

  DOI：10.1021/jo001534l

  日期：2001.5.1
• US6627629B2
  申请人：——

  公开号：US6627629B2

  公开（公告）日：2003-09-30