Fmoc-Aib-SA | 150458-43-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Aib-SA
• 英文别名: [2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methylpropanoyl] 2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methylpropanoate
• CAS: 150458-43-8
• 化学式: C₃₈H₃₆N₂O₇
• 分子量: 632.713
• InChiKey: CCEZCCVMUYMMMU-UHFFFAOYSA-N

物化性质

• 沸点：
  790.8±55.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.69
• 重原子数：
  47.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  120.03
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Fmoc-Aib-SA 、 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  First Interchain Peptide Interaction Detected by ESR in Fully Synthetic, Template-Assisted, Two-Helix Bundles

  摘要：

  We have designed and synthesized by solution methods two simple two-helix bundles based on a conformationally constrained cyclo-dipeptide template to the side chains of which two short, 2,2,6,6tetramethylpiperidine-1-oxyl-4-amino-4-carboxylic acid spin-monolabeled. 3(10)-helical peptides are covalently tethered. The preferred conformation of the appended chains has been assessed by FTIR absorption. The conclusions are corroborated by an X-ray diffraction analysis of one of the terminally blocked pentapeptide tails. For the first time, a solvent-dependent, inter-helix interaction has been monitored by conventional ESR spectroscopy on fully synthetic peptide systems. Half-field ESR measurements of these side-chain-substituted templates provided an experimental average distance between the two labels that is in good accord with that determined in a molecular modeling study.

  DOI：

  10.1021/ja992079h
• 作为产物：
  描述：

  Fmoc-2-氨基异丁酸 在 N,N'-二异丙基碳二亚胺 作用下， 生成 Fmoc-Aib-SA
  参考文献：
  名称：

  吡咯并[3,2- e ] [1,4]二氮杂-2-酮合成：可溶和不溶性载体的头对头比较

  摘要：

  芳基二氮杂-2-酮被称为“特权结构”，因为它们以高亲和力结合多种受体类型。为了开发新型的芳基二氮杂-2-酮骨架，从N开始探索在载体上的吡咯并[3,2- e ] [1,4]二氮杂-2-酮骨架的合成。-（PhF）-4-羟基脯氨酸，具有酸催化的Pictet-Spengler反应，形成二氮杂环。在杂环的合成中检查了三种载体[Wang树脂，四芳基phosph（TAP）可溶性载体和Merrifield树脂]，它们表现出不同的优缺点。通过在温和条件下裂解树脂后鉴定中间体，Wang树脂被证明对探索性合成的优化有效。但是，Pictet-Spengler反应的酸性条件导致树脂结合材料过早损失。借助TAP载体可以通过TLC，RP-HPLC-MS直接监测反应，在某些情况下还可以进行NMR光谱分析，这有助于通过沉淀纯化中间体。然而，材料的不完全沉淀导致总收率低于固相法树脂收率。事实证明，Merrifield树脂对吡咯并[3

  DOI：

  10.1021/jo200424q

文献信息

• Efficient coupling of α,α-dimethyl amino acid using a new chloro imidazolidium reagent, CIP
  作者：Kenichi Akaji、Naohiro Kuriyama、Yoshiaki Kiso

  DOI：10.1016/s0040-4039(00)76895-x

  日期：1994.5

  CIP (2-chloro- 1,3-dimethylimidazolidium hexafluorophosphate) was an efficient coupling agent for Nα-protected a-aminoisobutyric acid (Aib) in the presence of an additive. The reactivity was enhanced markedly by a catalytic amount of additive in the order of HOAt∼HODhbt > DMAP> HOBt. These couplings occurred without detectable racemization.

  CIP（2-氯-1,3- dimethylimidazolidium六氟磷酸盐）是一种有效的偶联剂对于N α -保护的一个在添加剂的存在下氨基异丁酸（Aib）。催化剂量按HOAt〜HODhbt> DMAP> HOBt的顺序显着提高了反应性。这些偶联发生时没有可检测的消旋作用。
• Complex Polyfluoride Additives in Fmoc-Amino Acid Fluoride Coupling Processes. Enhanced Reactivity and Avoidance of Stereomutation
  作者：Louis A. Carpino、Dumitru Ionescu、Ayman El-Faham、Michael Beyermann、Peter Henklein、Christiane Hanay、Holger Wenschuh、Michael Bienert

  DOI：10.1021/ol020235a

  日期：2003.4.1

  [reaction: see text] Isolated Fmoc amino acid fluorides have previously been shown to be among the most efficient reagents for peptide bond formation. Now, it has been found that anionic, polyhydrogen fluoride additives are capable of diverting many of the classical peptide coupling processes to acid fluoride couplings. Examples include the use of N-HBTU or N-HATU and the carbodiimide technique. As

  [反应：见正文]以前已证明，分离的Fmoc氨基酸氟化物是形成肽键最有效的试剂之一。现在，已经发现阴离子型聚氟化氢添加剂能够将许多经典的肽偶联方法转移至酸性氟化物偶联。示例包括使用N-HBTU或N-HATU以及碳二亚胺技术。作为含HF的物质，这些添加剂为耦合系统提供了更合适的介质，该系统对反应性羧基官能团的构型损失敏感。
• Rapid and efficient synthesis of peptide fragments containing α-aminoisobutyric acid using Fmoc-amino acid chlorides/potassium salt of 1-hydroxybenzotriazole
  作者：Vommina V. Suresh Babu、Hosahudya N. Gopi

  DOI：10.1016/s0040-4039(97)10724-9

  日期：1998.2

  The synthesis of peptides containing multiple Aib residues was accomplished using Fmoc-Aib-Cl in presence of KOBt. As no additional base was added, the duration of coupling reactions could be extended. Thus, the synthesis of the alamethicin 1–4 fragment, Aib-Pro-Aib-Ala, the emerimicin 2–6 fragment, Aib-Aib-Aib-Val-Gly and the Aib tetramer, Fmoc-(Aib)4-OBzl were accomplished in good yield and purity

  在KOBt存在下，使用Fmoc-Aib-Cl完成包含多个Aib残基的肽的合成。由于不添加额外的碱，可以延长偶联反应的持续时间。因此，合成了乐果霉素1-4片段，Aib-Pro-Aib-Ala，Emerimicin 2-6片段，Aib-Aib-Aib-Val-Gly和Aib四聚体，Fmoc-（Aib）4 -OBzl。以高收率和纯度完成。
• ESR Characterization of Hexameric, Helical Peptides Using Double TOAC Spin Labeling
  作者：Paul Hanson、Glenn Millhauser、Fernando Formaggio、Marco Crisma、Claudio Toniolo

  DOI：10.1021/ja961025u

  日期：1996.1.1

  Cα-tetrasubstituted amino acids, the hexameric sequences Boc-TOAC-Alan-TOAC-Ala4-n-OtBu were synthesized where n = 0−3 and TOAC is a spin label Aib analog. The peptides were studied by electron spin resonance (ESR) in four alcohols: MeOH, EtOH, TFE, and HFIP. Biradical J-coupling and dipolar interactions between the TOACs within each peptide were used to determine peptide geometry as a function of solvent

  α-氨基异丁酸 (Aib) 是一种 Cα-四取代氨基酸，非常有利于螺旋结构。为富含 Aib 的肽建立的大多数构象趋势已通过 X 射线晶体学确定。这些构象趋势是否会延续到质子溶剂是一个悬而未决的问题。为了开发探测含有 Cα-四取代氨基酸的肽的特性的通用策略，合成了六聚体序列 Boc-TOAC-Alan-TOAC-Ala4-n-OtBu，其中 n = 0-3，TOAC 是自旋标记Aib 模拟。通过电子自旋共振 (ESR) 在四种醇中研究这些肽：MeOH、EtOH、TFE 和 HFIP。每个肽内 TOAC 之间的双基 J 偶联和偶极相互作用用于确定肽几何形状作为溶剂的函数。在甲醇中，观察到与 310 螺旋的几何形状一致的强双自由基相互作用。溶剂显示出不同的趋势来支持螺旋结构，排序为 MeOH > EtOH > TFE > HFIP...。
• Convergent Synthesis of (−)-Mirabazole C Using a Chloroimidazolidium Coupling Reagent, CIP
  作者：Kenichi Akaji、Naohiro Kuriyama、Yoshiaki Kiso

  DOI：10.1021/jo952285h

  日期：1996.1.1

  Convergent synthesis of (-)-mirabazole C (1), a tetra thiazoline/thiazole alkaloid isolated from blue-green alga, has been described. The successive thiazoline rings of (-)-mirabazole C were formed by a single-step cyclization mediated by TiCl4 treatment of tripeptide amide 4. Convergent synthesis of the key intermediate 33 derived from three a-methylcysteine residues was first achieved using a newly developed coupling reagent, 2-chloro-1,3-dimethylimidazolidium hexafluorophosphate (CIP). The effectiveness of CIP for the coupling of alpha,alpha-dialkyl amino acids and the reaction pathway of the activation were clarified by the syntheses of model peptides containing an alpha,alpha-dimethylamino acid. A practical method of asymmetric synthesis of 2-methylcysteine by alkylation of 2,4-cis-oxazolidinone 23 has also been described.