t-Boc-Aib-Aib-OH | 79638-64-5

• 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: t-Boc-Aib-Aib-OH
• 英文别名: Boc-(Aib)₂-OH；N-tert-butoxycarbonyl α,α-dimethylglycyl α,α-dimethylglycine；N-Tert-Butoxycarbonyl alpha,alpha-Dimethylglycyl alpha,alpha-Dimethylglycine；2-methyl-2-[[2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoic acid
• CAS: 79638-64-5
• 化学式: C₁₃H₂₄N₂O₅
• 分子量: 288.344
• InChiKey: FSZVBYUGHWPVLI-UHFFFAOYSA-N

物化性质

• 沸点：
  487.0±30.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  t-Boc-Aib-Aib-OH 在 4-二甲氨基吡啶 、 正丁基锂 、 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 tert-butyl N-[1-[[1-[[1-[(2R,3S,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-2-oxopyrimidin-4-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]carbamate
  参考文献：
  名称：

  Synthesis of chemoreversible prodrugs of ara-C with variable time-release profiles. Biological evaluation of their apoptotic activity

  摘要：

  N-4-Dipeptidyl slow-release forms of the anticancer drug ara-C were prepared by acylation of the lithiated nucleotide with 4,4-dialkyloxazolinones. An azapeptide prodrug of am-C was obtained by condensation of an amino acid hydrazide with an activated nucleotide urea. The use of unnatural amino acid residues at N-4 prevented nonspecific proteolytic cleavage in biological medium. Aln-C prodrugs 10, 15, 17, and 19 released active drug with half-lives from a few minutes to several days, respectively. Activation via intramolecular N-4-deacylation did not require enzymatic intervention but was strictly dependent on the structure of the peptide chain. The prodrugs 10, 15, and 17 produced similar growth inhibition as ara-C in cultured murine leukemia cells while the azapeptide prodrug 19 was less potent reflecting the slow release of active drug with this compound. All four prodrugs retained the ability to induce apoptosis in human HL-60 leukemia cells with kinetics dictated by the rate of intramolecular N-4-deacylation. This the first demonstration for the control of apoptotic cell death by the modulation of drug release from prodrugs. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00153-8
• 作为产物：
  描述：

  Boc-Aib-Aib-OMe 在 lithium hydroxide monohydrate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 以83%的产率得到t-Boc-Aib-Aib-OH
  参考文献：
  名称：

  用单击化学装订3 10-螺旋

  摘要：

  短肽在药物发现和化学生物学中作为先导化合物和分子探针很重要，但是它们众所周知的缺点（例如高构象柔韧性，蛋白酶不稳定性，生物利用度差和体内半衰期短）阻碍了它们的潜力被充分利用。实现。侧链对侧链的环化，例如通过闭合烯烃复分解（称为钉合），是增加短肽的生物活性的一种方法，当应用于3 10和α-螺旋肽时，该方法已显示出希望。然而，关于原子分辨率结构信息，有关侧链对侧链环化在3 10中的作用-螺旋肽是稀缺的，报道的数据表明，改进现有方法学的潜力很大。在这里，我们报告了一种新型的吻合方法，用于在模型氨基异丁酸（Aib）丰富的肽中使用铜（I）催化的叠氮化物-炔烃环加成（CuAAC）反应的3个10螺旋肽，并研究了侧链至NMR，X射线衍射，线性IR和飞秒2D IR光谱分析侧链环化。我们的数据表明，所得环肽比其无环前体和迄今报道的其他钉合3 10-螺旋肽代表更理想的3 10-螺旋。当应用于3 10时，由CuA

  DOI：

  10.1021/jo101670a

文献信息

• Stapling of a 3₁₀-Helix with Click Chemistry
  作者：Øyvind Jacobsen、Hiroaki Maekawa、Nien-Hui Ge、Carl Henrik Görbitz、Pål Rongved、Ole Petter Ottersen、Mahmood Amiry-Moghaddam、Jo Klaveness

  DOI：10.1021/jo101670a

  日期：2011.3.4

  short peptides that has shown promise when applied to 310- and α-helical peptides. However, atomic resolution structural information on the effect of side chain-to-side chain cyclization in 310-helical peptides is scarce, and reported data suggest that there is significant potential for improvement of existing methodologies. Here, we report a novel stapling methodology for 310-helical peptides using

  短肽在药物发现和化学生物学中作为先导化合物和分子探针很重要，但是它们众所周知的缺点（例如高构象柔韧性，蛋白酶不稳定性，生物利用度差和体内半衰期短）阻碍了它们的潜力被充分利用。实现。侧链对侧链的环化，例如通过闭合烯烃复分解（称为钉合），是增加短肽的生物活性的一种方法，当应用于3 10和α-螺旋肽时，该方法已显示出希望。然而，关于原子分辨率结构信息，有关侧链对侧链环化在3 10中的作用-螺旋肽是稀缺的，报道的数据表明，改进现有方法学的潜力很大。在这里，我们报告了一种新型的吻合方法，用于在模型氨基异丁酸（Aib）丰富的肽中使用铜（I）催化的叠氮化物-炔烃环加成（CuAAC）反应的3个10螺旋肽，并研究了侧链至NMR，X射线衍射，线性IR和飞秒2D IR光谱分析侧链环化。我们的数据表明，所得环肽比其无环前体和迄今报道的其他钉合3 10-螺旋肽代表更理想的3 10-螺旋。当应用于3 10时，由CuA
• Peptides
  申请人：Jacobsen Øyvind

  公开号：US09227995B2

  公开（公告）日：2016-01-05

  A peptide which can adopt a 310-helical conformation in which the side chains of two amino acid residues in the peptide backbone are linked by a group comprising an aromatic 5-membered ring.

  一种肽，可以在其中两个氨基酸残基的侧链由包含芳香5元环的基团连接的310螺旋构象。
• Electron transfer through α-peptides attached to vertically aligned carbon nanotube arrays: a mechanistic transition
  作者：Jingxian Yu、Ondrej Zvarec、David M. Huang、Mark A. Bissett、Denis B. Scanlon、Joe G. Shapter、Andrew D. Abell

  DOI：10.1039/c2cc16665h

  日期：——

  The mechanism of electron transfer in α-aminoisobutyric (Aib) homoligomers is defined by the extent of secondary structure, rather than just chain length. Helical structures (Aib units ≥3) undergo an electron hopping mechanism, while shorter disordered sequences (Aib units <3) undergo an electron superexchange mechanism.

  δ-氨基异丁酸（Aib）均聚物中的电子传递机制是由二级结构的程度而不仅仅是链的长度决定的。螺旋结构（Aib单位≥3）采用电子跳跃机制，而较短的无序序列（Aib单位＜3）则采用电子超交换机制。
• Pavone, Vincenzo; Blasio, Benedetto Di; Lombardi, Angela, Journal of the Chemical Society. Perkin transactions II, 1992, # 8, p. 1233 - 1237
  作者：Pavone, Vincenzo、Blasio, Benedetto Di、Lombardi, Angela、Isernia, Carla、Pedone, Carlo、et al.

  DOI：——

  日期：——
• Conformational studies on peptides having chiral five-membered ring amino acid with two azido or triazole functional groups within the sequence of Aib residues
  作者：Makoto Oba、Naomi Kawabe、Hiroomi Takazaki、Yosuke Demizu、Mitsunobu Doi、Masaaki Kurihara、Hiroshi Suemune、Masakazu Tanaka

  DOI：10.1016/j.tet.2014.09.086

  日期：2014.11

  The chiral cyclic alpha,alpha-disubstituted alpha-amino acid, (3R,4R)-1-amino-3,4-diazido-1-cyclopentanecarboxylic acid [(R,R)-Ac-5C(dN3)], was introduced into achiral alpha-aminoisobutyric acid (Aib) peptides. The azido groups of (R,R)-Ac-5C(dN3) in the peptides were efficiently converted into 1,2,3-triazole functional groups. FTIR, H-1 NMR, and CD spectra revealed that the dominant conformations of all peptides in solution were 3(10)-helical structures without controlling the helical-screw sense. X-ray crystallographic analyses of peptides containing (R,R)-Ac-5C(dN3) showed that both the right-handed (P) and left-handed (M) 3(10)-helical structures were present in the crystal state. (C) 2014 Elsevier Ltd. All rights reserved.