(2S)-2-azido-5-bromovaleric acid | 203739-39-3

• 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: (2S)-2-azido-5-bromovaleric acid
• 英文别名: (2S)-azido-5-bromovaleric acid；2(S)-azido-5-bromovaleric acid；(2S)-2-azido-5-bromopentanoic acid
• CAS: 203739-39-3
• 化学式: C₅H₈BrN₃O₂
• 分子量: 222.041
• InChiKey: GAUZMAIGNSEMLL-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (2S)-2-azido-5-bromovaleric acid 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 苯 为溶剂， -15.0~20.0 ℃ 、206.84 kPa 条件下， 反应 28.09h， 生成 (2S)-2-amino-5-(2-imino-3-methylimidazolidin-1-yl)valeric acid
  参考文献：
  名称：

  Synthesis of Ethylene-Bridged (N^δ to N^ω) Analogues of Arginine

  摘要：

  DOI：

  10.1021/jo990551b
• 作为产物：
  描述：

  (S)-4-苄基-3-(5-溴戊基)噁唑烷-2-酮 在 lithium hydroxide 、 2,4,6-三异丙基苯磺酰叠氮化物 、 双氧水 、 双(三甲基硅烷基)氨基钾 作用下， 生成 (2S)-2-azido-5-bromovaleric 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 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.
• Selectivity enhancement induced by substitution of non-natural analogues of arginine and lysine in arginine-based thrombin inhibitors
  作者：Kyle P Kokko、Christine E Arrigoni、Thomas A Dix

  DOI：10.1016/s0960-894x(01)00328-6

  日期：2001.7

  Seven non-natural analogues of arginine and lysine have been substituted in an established arginine-based thrombin inhibitor. Four of the new compounds exhibited significant thrombin inhibition (K-i's 0.53-3.95 muM) and were subsequently tested for selectivity against trypsin. The two best compounds gave selectivity ratios of 962 and 525 (trypsin/thrombin), improving upon the parent compound. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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 of neurotensin(9–13) analogues exhibiting enhanced human neurotensin receptor binding affinities
  作者：Joseph T Lundquist、Erika E Büllesbach、Thomas A Dix

  DOI：10.1016/s0960-894x(00)00018-4

  日期：2000.3

  Recent evidence is consistent with neurotensin (NT)(8-13) adopting a Type I beta-turn conformation while binding the NT receptor, which would place the cationic side-chains of Arg(8) and Arg(9) in close proximity. This was the basis for the design, synthesis and analysis of truncated NT(9-13) analogues 1-5 with dicationic position 9 side-chains to emulate the functions of the 8 and 9 side-chains of NT(8-13). (C) 2000 Published by Elsevier Science Ltd. All rights reserved.
• 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.