(2S)-boc-4-amino-2-fluorobutyric acid | 135625-61-5

• 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: (2S)-boc-4-amino-2-fluorobutyric acid
• 英文别名: AFB-boc；(S)-4-(tert-butoxycarbonylamino)-2-fluorobutanoic acid；(2S)-2-fluoro-4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
• CAS: 135625-61-5
• 化学式: C₉H₁₆FNO₄
• 分子量: 221.229
• InChiKey: PCSNITIMCCDDPY-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  色胺 、 (2S)-boc-4-amino-2-fluorobutyric acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以66%的产率得到tert-butyl (SR)-4-(2-(1H-indol-3-yl)ethylamino)-3-fluoro-4-oxobutylcarbamate
  参考文献：
  名称：

  DNA sequence selectivity of hairpin polyamide turn units

  摘要：

  A class of hairpin polyamides linked by 3,4-diaminobutyric acid, resulting in a beta-amine residue at the turn unit, showed improved binding affinities relative to their alpha-amino-gamma-turn analogs for particular sequences. We incorporated beta-amino-gamma-turns in six-ring polyamides and determined whether there are any sequence preferences under the turn unit by quantitative footprinting titrations. Although there was an energetic penalty for G.C and C.G base pairs, we found little preference for T.A over A.T at the beta-amino- gamma-turn position. Fluorine and hydroxyl substituted alpha-amino-gamma-turns were synthesized for comparison. Their binding affinities and specificities in the context of six-ring polyamides demonstrated overall diminished affinity and no additional specificity at the turn position. We anticipate that this study will be a baseline for further investigation of the turn subunit as a recognition element for the DNA minor groove. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.072
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (S)-4-amino-2-fluorobutanoic acid hydrochloride 在 碳酸氢钠 作用下， 以 水 为溶剂， 以70%的产率得到(2S)-boc-4-amino-2-fluorobutyric acid
  参考文献：
  名称：

  DNA sequence selectivity of hairpin polyamide turn units

  摘要：

  A class of hairpin polyamides linked by 3,4-diaminobutyric acid, resulting in a beta-amine residue at the turn unit, showed improved binding affinities relative to their alpha-amino-gamma-turn analogs for particular sequences. We incorporated beta-amino-gamma-turns in six-ring polyamides and determined whether there are any sequence preferences under the turn unit by quantitative footprinting titrations. Although there was an energetic penalty for G.C and C.G base pairs, we found little preference for T.A over A.T at the beta-amino- gamma-turn position. Fluorine and hydroxyl substituted alpha-amino-gamma-turns were synthesized for comparison. Their binding affinities and specificities in the context of six-ring polyamides demonstrated overall diminished affinity and no additional specificity at the turn position. We anticipate that this study will be a baseline for further investigation of the turn subunit as a recognition element for the DNA minor groove. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.072

文献信息

• [EN] NOVEL ANTIBACTERIAL 3"-DERIVATIVES OF 4,6-DISUBSTITUTED 2,5-DIDEOXYSTREPTAMINE AMINOGLYCOSIDE ANTIBIOTICS<br/>[FR] NOUVEAUX DÉRIVÉS 3" ANTIBACTÉRIENS D'ANTIBIOTIQUES À BASE D'AMINOGLYCOSIDE 2,5-DIDÉSOXYSTREPTAMINE 4,6-DISUBSTITUÉS
  申请人：AGILEBIOTICS B V

  公开号：WO2020115190A1

  公开（公告）日：2020-06-11

  The present invention relates to novel aminoglycoside compounds having antimicrobial properties and being suitable, for example, as therapeutic agents for use in the treatment of mammalian disease and in particular to novel therapeutic agents suitable for use in the treatment of microbial infection in mammals. The present invention further relates to the use of pharmaceutical compositions comprising said agents in the treatment of medical conditions in mammals, in particular in the treatment of microbial infection. The agents and pharmaceutical compositions of the invention are of particular relevance in the treatment of diseases associated with antibiotic-resistant microbes. The invention further relates to compounds for use in the treatment of diseases whose treatment is made otherwise difficult due to antibiotic-class-related bacterial resistance and provides novel therapeutic agents suitable for use in the treatment of multidrug-resistant (MDR) infections.

  本发明涉及具有抗微生物特性的新型氨基糖苷化合物，适用于作为治疗剂，例如用于治疗哺乳动物疾病的治疗剂，特别是适用于治疗哺乳动物微生物感染的新型治疗剂。本发明还涉及包含所述治疗剂的药物组合物在治疗哺乳动物的医疗状况中的使用，特别是在治疗微生物感染中的使用。本发明的治疗剂和药物组合物在治疗与抗生素耐药微生物相关的疾病方面具有特殊意义。本发明还涉及用于治疗因抗生素类相关细菌耐药而导致治疗变得困难的疾病的化合物，并提供适用于治疗多药耐药（MDR）感染的新型治疗剂。
• NOVEL ANTIBACTERIAL 3"-DERIVATIVES OF 4,6-DISUBSTITUTED 2,5-DIDEOXYSTREPTAMINE AMINOGLYCOSIDE ANTIBIOTICS
  申请人：AGILeBiotics B.V.

  公开号：EP3891162A1

  公开（公告）日：2021-10-13
• Novel Antibacterial 3"-Derivatives Of 4,6-Disubstituted 2,5-Dideoxystreptamine Aminoglycoside Antibiotics
  申请人：AGILeBiotics B.V.

  公开号：US20220127297A1

  公开（公告）日：2022-04-28

  The present invention relates to novel aminoglycoside compounds having antimicrobial properties and being suitable, for example, as therapeutic agents for use in the treatment of mammalian disease and in particular to novel therapeutic agents suitable for use in the treatment of microbial infection in mammals. The present invention further relates to the use of pharmaceutical compositions comprising said agents in the treatment of medical conditions in mammals, in particular in the treatment of microbial infection. The agents and pharmaceutical compositions of the invention are of particular relevance in the treatment of diseases associated with antibiotic-resistant microbes. The invention further relates to compounds for use in the treatment of diseases whose treatment is made otherwise difficult due to antibiotic-class-related bacterial resistance and provides novel therapeutic agents suitable for use in the treatment of multidrug-resistant (MDR) infections.