2-(S)-azido-7-bromoheptanoic acid | 203739-41-7

• 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: 2-(S)-azido-7-bromoheptanoic acid
• 英文别名: 2(S)-azido-7-bromoheptanoic acid；(2S)-2-azido-7-bromoheptanoic acid
• CAS: 203739-41-7
• 化学式: C₇H₁₂BrN₃O₂
• 分子量: 250.095
• InChiKey: MGADCCHWSHLCNX-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  51.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(S)-azido-7-bromoheptanoic acid 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 (S)-2-{(2S,3S)-2-[(S)-2-({(S)-1-[(S)-2-((S)-2-Azido-7-dimethylamino-heptanoylamino)-5-guanidino-pentanoyl]-pyrrolidine-2-carbonyl}-amino)-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-pentanoylamino}-4-methyl-pentanoic acid
  参考文献：
  名称：

  Synthesis and Human Neurotensin Receptor Binding Activities of Neurotensin(8−13) Analogues Containing Position 8 α-Azido-N-alkylated Derivatives of Ornithine, Lysine, and Homolysine

  摘要：

  A series of neurotensin(8-13) (NT) analogues were synthesized through intermediates in which the N-terminal Arg(8) was replaced by various omega-bromo-2(S)-azido residues spanning 3-5 methylene units in side-chain length. Subsequent nucleophilic substitution of the omega-bromo groups with ammonia, methylamine, dimethylamine, or trimethylamine provided peptides containing N-terminal 2(S)-azido residues containing primary through quaternary N-alkylated side chains corresponding in length to ornithine, Lys, and homolysine. The synthetic procedure appears applicable for incorporation of a wide variety of amine-containing nonnatural amino acids into peptides. The particular modifications were intended to enhance physiochemical properties of NT(8-13) responsible for human NT 1 receptor (hNTR) binding, overall lipophilicity, and stability that may influence the potency of the peptides in vivo. When the peptides were tested for hNTR binding, the affinities in each series followed the order primary > secondary > tertiary > quaternary amine with the homolysine side-chain length being favored. All analogues possess binding affinities between acetyl-NT(8-13) and NT(8-13) indicating that the sterically less bulky alpha-azido may be inherently preferable to the acetyl group for N-terminal protection. This study extends the strategy of modifying amine-containing drugs through alkylations to peptide modification. The set of alkylated side chains also offers a new method of steric selection between receptor subtypes and could be used to modify the properties and biological effects of any peptide that contains cationic residues.

  DOI：

  10.1021/jm9903444
• 作为产物：
  描述：

  7-溴庚酸 在 lithium hydroxide 、 正丁基锂 、 2,4,6-三异丙基苯磺酰叠氮化物 、 双氧水 、 三甲基乙酰氯 、 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 生成 2-(S)-azido-7-bromoheptanoic acid
  参考文献：
  名称：

  Asymmetric synthesis of ω-bromo-2(S)-azido acids as precursors for the synthesis of novel amino acids

  摘要：

  A series of omega-bromo-2(S)-azido acids with side-chain lengths ranging from 3-5 methylene units has been synthesized. These intermediates enable the facile synthesis of chiral non-natural amino acids containing virtually any nucleophile capable of substituting the omega-bromo group. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10608-6

文献信息

• Synthesis of protected ω-mercapto amino acids: precursors for incorporation of elongated cysteines into peptides
  作者：Joseph T. Lundquist、Erika E. Büllesbach、Thomas A. Dix

  DOI：10.1016/s0957-4166(98)00261-4

  日期：1998.8

  A series of protected omega-mercapto amino acids with side-chain lengths ranging from 3-5 methylene units has been synthesized via nucleophilic substitution of omega-bromo-alpha-azido acids by 4-methoxy-alpha-toluenethiol followed by reduction of the azido functionality with SnCl2. These enantiomerically pure protected cysteine analogues can be used to optimize the length of disulfide connections in cyclically constrained peptide pharmacophores. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis and Human Neurotensin Receptor Binding Activities of Neurotensin(8−13) Analogues Containing Position 8 α-Azido-<i>N</i>-alkylated Derivatives of Ornithine, Lysine, and Homolysine
  作者：Lundquist、Thomas A. Dix

  DOI：10.1021/jm9903444

  日期：1999.11.1

  A series of neurotensin(8-13) (NT) analogues were synthesized through intermediates in which the N-terminal Arg(8) was replaced by various omega-bromo-2(S)-azido residues spanning 3-5 methylene units in side-chain length. Subsequent nucleophilic substitution of the omega-bromo groups with ammonia, methylamine, dimethylamine, or trimethylamine provided peptides containing N-terminal 2(S)-azido residues containing primary through quaternary N-alkylated side chains corresponding in length to ornithine, Lys, and homolysine. The synthetic procedure appears applicable for incorporation of a wide variety of amine-containing nonnatural amino acids into peptides. The particular modifications were intended to enhance physiochemical properties of NT(8-13) responsible for human NT 1 receptor (hNTR) binding, overall lipophilicity, and stability that may influence the potency of the peptides in vivo. When the peptides were tested for hNTR binding, the affinities in each series followed the order primary > secondary > tertiary > quaternary amine with the homolysine side-chain length being favored. All analogues possess binding affinities between acetyl-NT(8-13) and NT(8-13) indicating that the sterically less bulky alpha-azido may be inherently preferable to the acetyl group for N-terminal protection. This study extends the strategy of modifying amine-containing drugs through alkylations to peptide modification. The set of alkylated side chains also offers a new method of steric selection between receptor subtypes and could be used to modify the properties and biological effects of any peptide that contains cationic residues.
• Asymmetric synthesis of ω-bromo-2(S)-azido acids as precursors for the synthesis of novel amino acids
  作者：Joseph T. Lundquist、Thomas A. Dix

  DOI：10.1016/s0040-4039(97)10608-6

  日期：1998.2

  A series of omega-bromo-2(S)-azido acids with side-chain lengths ranging from 3-5 methylene units has been synthesized. These intermediates enable the facile synthesis of chiral non-natural amino acids containing virtually any nucleophile capable of substituting the omega-bromo group. (C) 1998 Elsevier Science Ltd. All rights reserved.