(R)-Fmoc-3-氨基-5-甲基己酸 | 212688-54-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: (R)-Fmoc-3-氨基-5-甲基己酸
• 英文名称: Fmoc-β³-(R)-homoleucine
• 英文别名: (R)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-methylhexanoic acid；(R)-Fmoc-β³hLeu-OH；(R)-Fmoc-β³homoleucine；Fmoc-(R)-β3hLeu-OH；(3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-methylhexanoic acid
• CAS: 212688-54-5
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: YLVSABQQLLRFIJ-OAHLLOKOSA-N

物化性质

• 沸点：
  572.1±33.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  (R)-Fmoc-3-氨基-5-甲基己酸 、 在 N-羟基-7-氮杂苯并三氮唑 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成
  参考文献：
  名称：

  Macrolide Inspired Macrocycles as Modulators of the IL-17A/IL-17RA Interaction

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c00327

文献信息

• Synthesis and Biological Evaluation of Gramicidin S-Inspired Cyclic Mixed<i>α</i>/<i>β</i>-Peptides
  作者：Matthijs van der Knaap、Fatih Basalan、Henny C. van de Mei、Henk J. Busscher、Gijsbert A. van der Marel、Herman S. Overkleeft、Mark Overhand

  DOI：10.1002/cbdv.201200277

  日期：2012.11

  β(2)-amino acids (R)- and (S)-Fmoc-β(2)homovaline and (R)-Fmoc-β(2)homoleucine are synthesized. These building blocks were used, in combination with commercially available α- and β(3)-amino acids, for the synthesis of the cyclo-(αβ(3)αβ(2)α)(2) peptide 2 and the cyclo-(αβ(2)αβ(3)α)(2) peptides 3-5. The peptides 2-5 were screened for their ability to inhibit a small panel of Gram-negative and Gram-positive bacterial

  通过涉及二苄基亚胺类物质和埃文斯手性酰化恶唑烷酮的钛烯酸酯的曼尼希反应，β（2）-氨基酸（R）-和（S）-Fmoc-β（2）同卵磷脂和（R）-Fmoc-β （2）合成了高亮氨酸。这些构件与可商购的α-和β（3）-氨基酸结合使用，用于合成环-（αβ（3）αβ（2）α）（2）肽2和​​环-（ αβ（2）αβ（3）α）（2）肽3-5。筛选肽2-5抑制一小批革兰氏阴性和革兰氏阳性细菌菌株的能力。
• Design, synthesis and structural analysis of mixed α/β-peptides that adopt stable cyclic hairpin-like conformations
  作者：Matthijs van der Knaap、José M. Otero、Antonio Llamas-Saiz、Mark J. van Raaij、Lianne I. Lageveen、Henk J. Busscher、Gijsbert M. Grotenbreg、Gijsbert A. van der Marel、Herman S. Overkleeft、Mark Overhand

  DOI：10.1016/j.tet.2012.01.015

  日期：2012.3

  replacement of four α-amino acid residues of a cyclo-(ααααα)2 peptide by β-, β2- or β3-amino acids residues provided a series of novel 2:1 α/β-mixed peptides that were designed to adopt cyclic hairpin-like structures. It was shown that conformationally stable cyclo-(αβαβα)2 isomers can be obtained using both enantiomers of the central two basic α-amino acid residues, a known α-amino acid turn sequence and several

  战略更换四个α氨基的一个氨基酸残基的环- （ααααα）2肽通过β-，β 2 -和β 3 -氨基酸残基而提供一系列新2:1α/β混合的肽设计，即采用环状发夹状结构。结果表明，构象稳定的环-（αβαβα）2异构体可以使用中心两个碱性α-氨基酸残基的两个对映异构体，已知的α-氨基酸转向序列以及没有侧链或具有特定区域和区域的疏水性侧链的面对的β-氨基酸残基的几种组合来获得。立体化学。两种衍生物的X射线分析提供了分子内氢键相互作用，主链二面角和新型环状发夹状结构的侧链位置的分子细节。这些异构体之一在晶体结构中形成了前所未有的六边形纳米通道组件。
• Enzymatic C‐to‐C Protein Ligation
  作者：Fabian B. H. Rehm、Tristan J. Tyler、Simon J. Veer、David J. Craik、Thomas Durek

  DOI：10.1002/anie.202116672

  日期：2022.3.7

  including a C-terminal reversed sequence mimetic of the native N-terminal substrate is reported. This retro substrate mimetic can be introduced onto recombinant proteins and synthetic peptides, enabling enzyme-catalyzed protein or peptide C-to-C ligation.

  据报道，天冬酰胺酰连接酶（一种高效转肽酶）的底物模拟物的开发，包括天然 N 端底物的 C 端反向序列模拟物。这种逆转录底物模拟物可以引入到重组蛋白和合成肽上，从而实现酶催化的蛋白质或肽 C 到 C 连接。
• Use of Parallel Synthesis To Probe Structure−Activity Relationships among 12-Helical β-Peptides:  Evidence of a Limit on Antimicrobial Activity
  作者：Emilie A. Porter、Bernard Weisblum、Samuel H. Gellman

  DOI：10.1021/ja0519785

  日期：2005.8.1

  We report structure-activity trends among helix-forming beta-amino acid oligomers that are intended to mimic alpha-helical host-defense peptides. Parallel synthesis of two small, focused beta-peptide libraries allowed us to identify relatively short (11-residue) beta-peptides that display antimicrobial activity. These beta-peptides exhibit selectivity for bacteria relative to human red blood cells. A large hydrophobic helical surface is necessary for antimicrobial activity. Longer analogues (16 residues) of the most active library members were prepared and evaluated. Some of these longer beta-peptides showed very good antimicrobial activity, but none was more active than a previously reported beta-peptide [Porter, E. A.; Wang, X.; Lee, H.-S.; Weisblum, B.; Gellman, S. H. Nature 2000, 404, 565]. The extensive literature on a-helical host-defense peptides and related alpha-peptides indicates that such molecules are seldom active at concentrations below 1 mu g/mL, and our results suggest that amphiphilic helical beta-peptides are subject to a comparable limit.
• WO2023/225534
  申请人：——

  公开号：——

  公开（公告）日：——