Nα-Z-Nγ-Fmoc-L-2,4-diaminobutyric acid | 151132-82-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Nα-Z-Nγ-Fmoc-L-2,4-diaminobutyric acid
• 英文别名: Z-L-Dab(Fmoc)-OH；(2S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-2-(phenylmethoxycarbonylamino)butanoic acid
• CAS: 151132-82-0
• 化学式: C₂₇H₂₆N₂O₆
• 分子量: 474.513
• InChiKey: XVQCVMKVEGLEGU-DEOSSOPVSA-N

物化性质

• 沸点：
  739.8±60.0 °C(Predicted)
• 密度：
  1.299

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Nα-Z-Nγ-Fmoc-L-2,4-diaminobutyric acid 在 哌啶 、 sodium tetrahydroborate 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 、 溶剂黄146 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 47.0h， 生成
  参考文献：
  名称：

  Metal chelating amino acids in the design of peptides and proteins. Synthesis of Nα-Fmoc/But protected amino acids incorporating aminodiacetic acid moiety.

  摘要：

  The synthesis of Fmoc/Bu(t) protected amino acid chelators 14, 15, 16 and 24 is described. With respect to their Boc/Bzl derivatives, the title compounds offer synthetic advantage: Peptide Ac-Ada(1)-Ala3-Ada(1)-Ala4-Glu-Lys-NH2 was assembled by Solid PPS in 74.2% yield.

  DOI：

  10.1016/0040-4039(93)88067-s
• 作为产物：
  描述：

  methyl (2S)-4-amino-2-{[(benzyloxy)carbonyl]amino}butanoate 在 sodium hydroxide 、 sodium carbonate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 7.0h， 生成 Nα-Z-Nγ-Fmoc-L-2,4-diaminobutyric acid
  参考文献：
  名称：

  Modification of receptor selectivity and functional activity of cyclic cholecystokinin analogues

  摘要：

  We reported earlier on the synthesis and biological activity at the CCK-B receptor of cyclized derivatives of CCK. These peptides, in which the positions 28 and 31 were replaced by lysine residues, were bridged by a succinyl moiety. To determine the importance Of the nature and size of the cyclic structure, cyclic analogues were synthesized in which: (i) the lysine residues were replaced by ornithine and diaminobutyric acid and (ii) the succinic moiety was replaced by a malonic, adipic and glutaric moiety. They were tested for their ability to inhibit the specific binding of I-125-BH-CCK-8 to CCK receptors in rat pancreatic acini and guinea pig brain membranes. They were also evaluated for their ability to stimulate amylase secretion from rat pancreatic acini. The potency and selectivity of these analogues were compared with those obtained with CCK-4 and compound JMV320, a potent and selective CCK-B receptor ligand synthesized earlier in our laboratory. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80006-8

文献信息

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

  公开号：WO2020014469A1

  公开（公告）日：2020-01-16

  Compositions and methods for the treatment of bacterial infections including compounds containing dimers of cyclic heptapeptides. 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的化合物。特别地，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。
• [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES
  申请人：CIDARA THERAPEUTICS INC

  公开号：WO2019126341A3

  公开（公告）日：2019-09-12
• Synthesis and evaluation of novel dipeptide-bound 1,2,4-Thiadiazoles as irreversible inhibitors of guinea pig liver transglutaminase
  作者：Claudio Marrano、Pierre de Macédo、Paul Gagnon、Danielle Lapierre、Christian Gravel、Jeffrey W Keillor

  DOI：10.1016/s0968-0896(01)00228-0

  日期：2001.12

  Herein we report the synthesis and evaluation of 14 novel peptides as potential irreversible inactivators of guinea pig liver transglutaminase (TGase). These peptides were designed to resemble Cbz-L-Gln-Gly, known to be a good TGase substrate, and to include a 1,2,4-thiadiazole group. The side chain length of the amino acid residue bearing the inhibitor group was also varied in order to permit investigation of this effect. Their inactivation rate constants were measured using a direct continuous spectrophotometric method and were found to vary between 0.330 to 0.89 muM min(-1). (C) 2001 Elsevier Science Ltd. All rights reserved.
• MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS
  申请人：RQX PHARMACEUTICALS, INC.

  公开号：US20180327367A1

  公开（公告）日：2018-11-15

  Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidase (SpsB), an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.
• Metal chelating amino acids in the design of peptides and proteins. Synthesis of Nα-Fmoc/But protected amino acids incorporating aminodiacetic acid moiety.
  作者：Wieslaw M. Kazmierski

  DOI：10.1016/0040-4039(93)88067-s

  日期：1993.7

  The synthesis of Fmoc/Bu(t) protected amino acid chelators 14, 15, 16 and 24 is described. With respect to their Boc/Bzl derivatives, the title compounds offer synthetic advantage: Peptide Ac-Ada(1)-Ala3-Ada(1)-Ala4-Glu-Lys-NH2 was assembled by Solid PPS in 74.2% yield.