N4-(苄氧羰基)-L-2,4-二氨基丁酸 | 2130-77-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N4-(苄氧羰基)-L-2,4-二氨基丁酸
• 中文别名: N'-苄氧羰基-L-2,4-二氨基丁酸盐酸盐
• 英文名称: (S)-2-Amino-4-benzyloxycarbonylamino-butyric acid
• 英文别名: H-DAB(Cbz)-OH；N^γ-benzyloxycarbonyl-L-α,γ-diaminobutyric acid；(2S)-N⁴-benzyloxycarbonyl-2,4-diaminobutanoic acid；ε-Benzyloxycarbonyl-L-α,γ-diamino-buttersaeure；N^γ-Carbobenzoxy-L-α,γ-diaminobuttersaeure；γ-N-Carbobenzoxyl-L-α,γ-diaminobuttersaeure；N^γ-Z-L-α,γ-Diamino-buttersaeure；(S)-2-Amino-4-benzyloxycarbonylamino-buttersaeure；(2S)-2-Amino-4-{[(benzyloxy)carbonyl]amino}butanoic acid；(2S)-2-amino-4-(phenylmethoxycarbonylamino)butanoic acid
• CAS: 2130-77-0
• 化学式: C₁₂H₁₆N₂O₄
• 分子量: 252.27
• InChiKey: SDFDIECLEXOBAG-JTQLQIEISA-N

物化性质

• 熔点：
  225-227 °C
• 沸点：
  483.2±45.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  N4-(苄氧羰基)-L-2,4-二氨基丁酸 在 盐酸 作用下， 生成 N-gamma-苄氧羰基-L-alpha,gamma-二氨基丁酸甲酯盐酸盐
  参考文献：
  名称：

  Kurihara; Suzuki, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1955, vol. 75, p. 1269,1271

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-2-amino-4-benzyloxycarbonylamino-butyric acid ; copper (II)-salt 在 硫化氢 、 水 作用下， 生成 N4-(苄氧羰基)-L-2,4-二氨基丁酸
  参考文献：
  名称：

  潜在的大环肽基硼酸作为胰凝乳蛋白酶抑制剂。

  摘要：

  用复杂的硼酸类似物7、8-OH和8-NH（2）（）探索了在丝氨酸蛋白酶活性位点形成肽硼酸酯加合物的可能性，该位点模仿肽水解机理中的第一个四面体中间体。在这些结构中，P（1）和P（2）残基以及P（1）'-P（3）'残基通过P（2）和P（1）'侧链连接，以鼓励形成经由大环化的二酯或酰胺酯加合物。这些抑制剂由2，4-二氨基丁酸或2，4-二氨基戊酸（11），硼苯丙氨酸（12），天冬氨酸，苹果酸或取代的苹果酸类似物13和Leu-Arg二肽的适当保护的衍生物组装而成。为（S，S）-2，4-二氨基戊酸酯11和（S，S）-β-异丁基苹果酸酯13衍生物开发了立体选择性合成。复杂的硼酸肽基酯7（K（i）= 26 nM）和8-OH（68 nM）是α-胰凝乳蛋白酶的有效抑制剂。然而，7的亲和力既不依赖于时间，也不依赖于pH值，仅适度地大于8-H（114 nM），9（356 nM）和10（219 nM）不能比较的比较化合物。环化或形成二酯加合物。

  DOI：

  10.1021/jo9615007

文献信息

• RGD Mimetics containing a central hydantoin scaffold: α V β 3 vs α IIb β 3 selectivity requirements
  作者：Anusch Peyman、Volkmar Wehner、Jochen Knolle、Hans Ulrich Stilz、Gerhard Breipohl、Karl-Heinz Scheunemann、Denis Carniato、Jean-Marie Ruxer、Jean-Francois Gourvest、Thomas R Gadek、Sarah Bodary

  DOI：10.1016/s0960-894x(99)00661-7

  日期：2000.1

  The synthesis of a series of RGD mimetic alpha(v)beta3 antagonists containing a hydantoin scaffold is shown. The results demonstrate some of the structural requirements for the design of selective alpha(v)beta3 antagonists (vs alpha(IIb)beta3) in terms of the Arg-mimetic, the distance between N- and C-terminus and the lipophilic side chain.

  显示了一系列包含乙内酰脲支架的RGD模拟α（v）beta3拮抗剂的合成。结果表明，根据Arg-拟态，N-和C-末端之间的距离以及亲脂性侧链设计选择性α（v）beta3拮抗剂（vs alpha（IIb）beta3）的一些结构要求。
• Synthesen in der Polymyxin-Reihe 1. Mitteilung. Synthese eines Pentapeptid-Fragmentes
  作者：K. Vogler、P. Lanz

  DOI：10.1002/hlca.19600430136

  日期：——

  The protected pentapeptide formyl-L-leucyl-Nγ-benzyloxycarbonyl-L-α,γ-diaminobutyryl-Nγ-benzyloxycarbonyl-L-α,γ-diaminobutyryl-L-threonyl-Nγ-benzyloxycarbonyl-L-α,γ-diaminobutyric acid, a sequence which is known to occur in the polymyxins, has been synthesized. Different coupling methods including the azide route lead to the same end product, with the same optical rotation. We therefore believe our

  被保护的五肽甲酰基-L-亮氨酰基-N γ -苄氧羰基-L-α，γ二氨-N γ -苄氧羰基-L-α，γ二氨-L-苏-N γ -苄氧羰基-L-α，γ-已经合成了已知在多粘菌素中存在的序列二氨基丁酸。包括叠氮化物路线在内的不同耦合方法导致相同的最终产品具有相同的旋光度。因此，我们认为我们的五肽是光学纯的。
• A New Approach to the Synthesis of Selectively Protected (2<i>S</i>)-1,2,4-Triaminobutane Derivatives
  作者：Adam P. Treder、Aleksandra Walkowiak、Włodzimierz Zgoda、Ryszard Andruszkiewicz

  DOI：10.1055/s-2005-869989

  日期：——

  An efficient synthesis of selectively protected (25)-1,2,4-triaminobutane from L-glutamic acid via (25)-N 4 -benzyloxy-carbonyl-2,4-diaminobutanamid is described.

  描述了通过 (25)-N 4 -benzyloxy-carbonyl-2,4-diaminobutanamid 由 L-谷氨酸选择性保护的 (25)-1,2,4-三氨基丁烷的有效合成。
• Development of dilipid polymyxins: Investigation on the effect of hydrophobicity through its fatty acyl component
  作者：Ronald Domalaon、Liam Berry、Quinn Tays、George G. Zhanel、Frank Schweizer

  DOI：10.1016/j.bioorg.2018.07.018

  日期：2018.10

  Continuous development of new antibacterial agents is necessary to counter the problem of antimicrobial resistance. Polymyxins are considered as drugs of last resort to combat multidrug-resistant Gram-negative pathogens. Structural optimization of polymyxins requires an in-depth understanding of its structure and how it relates to its antibacterial activity. Herein, the effect of hydrophobicity was explored by adding a secondary fatty acyl component of varying length onto the polymyxin structure at the amine side-chain of c-diaminobutyric acid at position 1, resulting to the development of dilipid polymyxins. The incorporation of an additional lipid was found to confer polymyxin activity against Gram-positive bacteria, to which polymyxins are inherently inactive against. The dilipid polymyxins showed selective antibacterial activity against Pseudomonas aeruginosa. Moreover, dilipid polymyxin 1 that consists of four carbon-long aliphatic lipids displayed the ability to enhance the antibacterial potency of other antibiotics in combination against P. aeruginosa, resembling the adjuvant activity of the well-known outer membrane permeabilizer polymyxin B nonapeptide (PMBN). Interestingly, our data revealed that dilipid polymyxin 1 and PMBN are substrates for the MexAB-OprM efflux system, and therefore are affected by efflux. In contrast, dilipid polymyxin analogs that consist of longer lipids and colistin were not affected by efflux, suggesting that the lipid component of polymyxin plays an important role in resisting active efflux. Our work described herein provides an understanding to the polymyxin structure that may be used to usher the development of enhanced polymyxin analogs.
• Zaoral et al., Chemicke Listy, 1953, vol. 47, p. 427,428,439
  作者：Zaoral et al.

  DOI：——

  日期：——