(1R,2S)-2-Aminomethyl-1-tert-butoxycarbonylamino-cyclopropanecarboxylic acid | 154801-55-5

• 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)-2-Aminomethyl-1-tert-butoxycarbonylamino-cyclopropanecarboxylic acid
• 英文别名: (1R,2S)-2-(aminomethyl)-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropane-1-carboxylic acid
• CAS: 154801-55-5
• 化学式: C₁₀H₁₈N₂O₄
• 分子量: 230.264
• InChiKey: SFVAJDYUCWSXER-QUBYGPBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-Aminomethyl-1-tert-butoxycarbonylamino-cyclopropanecarboxylic acid 在 sodium hydroxide 、 氨 、 silver nitrate 、 三氟乙酸 作用下， 以 四氯化碳 、 乙醇 、 乙腈 为溶剂， 反应 16.83h， 生成 (1R,2S)-1-Amino-2-[({amino-[(Z)-4-methoxy-2,3,6-trimethyl-benzenesulfonylimino]-methyl}-amino)-methyl]-cyclopropanecarboxylic acid
  参考文献：
  名称：

  Asymmetric Syntheses of Protected Derivatives of Carnosadine and Its Stereoisomers as Conformationally Constrained Surrogates for Arginine

  摘要：

  All four stereoisomers of carnosadine were shown to be accessible from the lactone 1 or the diester 10 (or their enantiomers). Members of the cis series (Z-cyclo-Arg') were obtained via a sequence involving opening lactone 1 with ammonia, Hofmann rearrangement, and incorporation of the guanidine group via an azide (3). The trans series (i.e. The E-cyclo-Arg' series) was prepared via a route which is similar, except that it begins with hydrolysis of the less hindered ester functionality of diester 10. Products from both series were manipulated into protected forms for peptide synthesis using the BOC or the FMOC approach.

  DOI：

  10.1021/jo00087a039
• 作为产物：
  描述：

  ethyl (1R,2R)-1-(tert-butoxycarbonylamino)-2-(hydroxymethyl)cyclopropane-1-carboxylate 在 palladium on activated charcoal sodium hydroxide 、 sodium azide 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.0h， 生成 (1R,2S)-2-Aminomethyl-1-tert-butoxycarbonylamino-cyclopropanecarboxylic acid
  参考文献：
  名称：

  Asymmetric Syntheses of Protected Derivatives of Carnosadine and Its Stereoisomers as Conformationally Constrained Surrogates for Arginine

  摘要：

  All four stereoisomers of carnosadine were shown to be accessible from the lactone 1 or the diester 10 (or their enantiomers). Members of the cis series (Z-cyclo-Arg') were obtained via a sequence involving opening lactone 1 with ammonia, Hofmann rearrangement, and incorporation of the guanidine group via an azide (3). The trans series (i.e. The E-cyclo-Arg' series) was prepared via a route which is similar, except that it begins with hydrolysis of the less hindered ester functionality of diester 10. Products from both series were manipulated into protected forms for peptide synthesis using the BOC or the FMOC approach.

  DOI：

  10.1021/jo00087a039

文献信息

• Stalobacin: Discovery of Novel Lipopeptide Antibiotics with Potent Antibacterial Activity against Multidrug-Resistant Bacteria
  作者：Kouhei Matsui、Yukiko Kan、Junko Kikuchi、Keisuke Matsushima、Miki Takemura、Hideki Maki、Iori Kozono、Taichi Ueda、Kazuyuki Minagawa

  DOI：10.1021/acs.jmedchem.0c00295

  日期：2020.6.11

  A novel lipopeptide antibiotic, stalobacin I (1), was discovered from a culture broth of an unidentified Gram-negative bacterium. Stalobacin I (1) had a unique chemical architecture composed of an upper and a lower half peptide sequence, which were linked via a hemiaminal methylene moiety. The sequence of 1 contained an unusual amino acid, carnosadine, 3,4-dihydroxyariginine, 3-hydroxyisoleucine, and

  从未知革兰氏阴性细菌的培养液中发现了一种新的脂肽抗生素司他巴星I（1）。Stalobacin I（1）具有独特的化学结构，该结构由上半部分和下半部分肽序列组成，它们通过半胱氨酸亚甲基部分相连。1的序列包含一个不寻常的氨基酸，卡诺萨丁，3,4-二羟基精氨酸，3-羟基异亮氨酸和3-羟基天冬氨酸，以及一种新型的环丙基脂肪酸。1对多种耐药革兰氏阳性细菌的抗菌活性比万古霉素，利奈唑胺和特拉万星（MIC 0.004-0.016μg/ mL）等“最后使用”的抗生素要强得多。此外，化合物1通过膨胀细菌细胞体诱导革兰氏阳性和革兰氏阴性菌株的特征形态变化。通过对其立体异构体的合成研究，确定了环丙基氨基酸卡诺沙丁的绝对构型，这是1的强活性必不可少的组成部分。
• Asymmetric Syntheses of Protected Derivatives of Carnosadine and Its Stereoisomers as Conformationally Constrained Surrogates for Arginine
  作者：Kevin Burgess、Dongyeol Lim、Kwok-Kan Ho、Chun-Yen Ke

  DOI：10.1021/jo00087a039

  日期：1994.4

  All four stereoisomers of carnosadine were shown to be accessible from the lactone 1 or the diester 10 (or their enantiomers). Members of the cis series (Z-cyclo-Arg') were obtained via a sequence involving opening lactone 1 with ammonia, Hofmann rearrangement, and incorporation of the guanidine group via an azide (3). The trans series (i.e. The E-cyclo-Arg' series) was prepared via a route which is similar, except that it begins with hydrolysis of the less hindered ester functionality of diester 10. Products from both series were manipulated into protected forms for peptide synthesis using the BOC or the FMOC approach.