N^α-benzyloxycarbonyl-β-guanidino-L-α-alanine | 281666-49-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N^α-benzyloxycarbonyl-β-guanidino-L-α-alanine
• 英文别名: N-[(benzyloxy)carbonyl]-3-carbamimidamido-L-alanine；3-[(Aminoiminomethyl)amino]-N-[(phenylmethoxy)carbonyl]-L-alanine；(2S)-3-(diaminomethylideneamino)-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 281666-49-7
• 化学式: C₁₂H₁₆N₄O₄
• 分子量: 280.283
• InChiKey: FBGBJNQYCQFLAH-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,5,7,8-五甲基苯并二氢吡喃-6-磺酰氯 、 N^α-benzyloxycarbonyl-β-guanidino-L-α-alanine 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以52%的产率得到Nα-benzyloxycarbonyl-β-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)guanidino-L-α-alanine
  参考文献：
  名称：

  Synthesis of Alanine and Proline Amino Acids with Amino or Guanidinium Substitution on the Side Chain

  摘要：

  Competitive binding of peptides containing basic amino acids to disrupt or prevent the Tat-TAR interaction could result in diminished transcription as well as translation and hence constitutes an alternative way of controlling HN replication. Therefore, we synthesized guanidinium and amino containing amino acids, based on a proline or an alanine scaffold. The introduction of the guanidinium moiety was best accomplished using 1H-pyrazole-1-carboxamidine hydrochloride, with Pmc used for its protection. The absence of racemization, maintained throughout the whole synthesis, was confirmed by chiral purity determination. These building blocks were smoothly incorporated into oligopeptides, which proved their suitability for use in a combinatorial approach for selecting TAR binding ligands. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00123-x
• 作为产物：
  描述：

  N-苄氧羰基-L-天冬酰胺 在 吡啶 、 sodium carbonate 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 N^α-benzyloxycarbonyl-β-guanidino-L-α-alanine
  参考文献：
  名称：

  Synthesis of Alanine and Proline Amino Acids with Amino or Guanidinium Substitution on the Side Chain

  摘要：

  Competitive binding of peptides containing basic amino acids to disrupt or prevent the Tat-TAR interaction could result in diminished transcription as well as translation and hence constitutes an alternative way of controlling HN replication. Therefore, we synthesized guanidinium and amino containing amino acids, based on a proline or an alanine scaffold. The introduction of the guanidinium moiety was best accomplished using 1H-pyrazole-1-carboxamidine hydrochloride, with Pmc used for its protection. The absence of racemization, maintained throughout the whole synthesis, was confirmed by chiral purity determination. These building blocks were smoothly incorporated into oligopeptides, which proved their suitability for use in a combinatorial approach for selecting TAR binding ligands. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00123-x

文献信息

• [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS<br/>[FR] COMPOSÉS ET MÉTHODES POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES
  申请人：CIDARA THERAPEUTICS INC

  公开号：WO2018006063A1

  公开（公告）日：2018-01-04

  Compositions and methods for the treatment of bacterial infections include compounds containing dimers of cyclic heptapeptides conjugated to one or more monosaccharide or oligosaccharide moieties. In particular, compounds can be used in the treatment of bacterial infections caused by Gram-negative bacteria.

  用于治疗细菌感染的组合物和方法包括含有环七肽二聚体与一个或多个单糖或寡糖基团结合的化合物。特别是，这些化合物可用于治疗由革兰氏阴性细菌引起的细菌感染。