Boc-Ile-O-COOiBu | 66866-47-5

• 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: Boc-Ile-O-COOiBu
• 英文别名: 2-methylpropoxycarbonyl (2S,3S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 66866-47-5
• 化学式: C₁₆H₂₉NO₆
• 分子量: 331.409
• InChiKey: GXJUNTFPZAEEAN-RYUDHWBXSA-N

物化性质

• 密度：
  1.058±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Ile-O-COOiBu 在 sodium tetrahydroborate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 以430 mg的产率得到N-Boc-L-异亮氨醇
  参考文献：
  名称：

  RTD-1Mimic Containing γPNA Scaffold Exhibits Broad-Spectrum Antibacterial Activities

  摘要：

  Macrocyclic peptides with multiple disulfide cross-linkages, such as those produced by plants and those found in nonhuman primates, as components of the innate immunity, hold great promise for molecular therapy because of their broad biological activities and high chemical, thermal, and enzymatic stability. However, for some, because of their intricate spatial arrangement and elaborate interstrand cross-linkages, they are difficult to prepare de novo in large quantities and high purity, due to the nonselective nature of disulfide-bond formation. We show that the disulfide bridges of RTD-1, a member of the theta-defensin subfamily, could be replaced with noncovalent Watson Crick hydrogen bonds without significantly affecting its biological activities. The work provides a general strategy for engineering conformationally rigid, cyclic peptides without the need for disulfide-bond reinforcement.

  DOI：

  10.1021/ja211867j
• 作为产物：
  描述：

  BOC-L-异亮氨酸 、 氯甲酸异丁酯 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 Boc-Ile-O-COOiBu
  参考文献：
  名称：

  C 2对称手性二胺-铜（II）配合物 催化对映选择性亨利反应†

  摘要：

  事实证明，C 2对称二胺的铜（II）络合物是硝基链烷烃与各种醛之间对映选择性亨利反应的有效催化剂，以高产率（高达97％），中等非对映选择性（高达90％以上）提供β-羟基硝基链烷烃。至71:29）和出色的对映体过量（高达96％）。所获得的手性硝基醛醇加合物在几个步骤中已进一步转化为手性氮丙啶。

  DOI：

  10.1039/b904254g

文献信息

• Synthesis and biological evaluation of analogs of Pro-Leu-Gly-NH2 modified at the leucyl residue
  作者：Rodney L. Johnson、Roger J. Bontems、Kaipeen E. Yang、Ram K. Mishra

  DOI：10.1021/jm00168a045

  日期：1990.6

  analogues were tested for their ability to enhance the binding of the dopamine receptor agonist 2-amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalene (ADTN) to striatal dopamine receptors. Two of the above analogues, Pro-Ahx-Gly-NH2 (3) and Pro-Phe-Gly-NH2 (6), showed significant activity in this assay system. Pro-Ahx-Gly-NH2 produced a 16% enhancement of ADTN binding at 0.1 microM, while Pro-Phe-Gly-NH2

  Pro-Leu-Gly-NH2（PLG）的一系列类似物，其中亮氨酸残基已被脂族氨基酸L-异亮氨酸，L-2-氨基己酸（Ahx），L-2-氨基戊酸和已经合成了L-2-氨基丁酸和芳族氨基酸L-苯基丙氨酸，L-苯基甘氨酸，L-和D-2-氨基-4-苯基丁酸，LO-甲基酪氨酸和L-4-硝基苯基丙氨酸。测试了这些类似物增强多巴胺受体激动剂2-氨基-6,7-二羟基-1,2,3,4-四氢萘（ADTN）与纹状体多巴胺受体结合的能力。上述两个类似物Pro-Ahx-Gly-NH2（3）和Pro-Phe-Gly-NH2（6）在此测定系统中显示出显着活性。Pro-Ahx-Gly-NH2在0.1 microM时可提高16％的ADTN结合力，
• Coupling Reagent Dependent Regioselectivity in the Synthesis of Lysine Dipeptides
  作者：Shimon Shatzmiller、Pat N. Confalone、Ariela Abiri

  DOI：10.1055/s-1999-3178

  日期：——

  Participation of either the Nℇ or Nα of l-methyl lysinate (2) in peptide bond formation could be selectively achieved by the use of either isobutyl chloroformate (method A) or N,N-bis(2-oxo-3-oxazolidinyl) phosphinic chloride (BOP-Cl) (method B), respectively. The amidation performed according to method A gives high yields of the dipeptides 3a-e, irrespective of the amino acids used. In method B, Nα amidation is highly preferred especially with bulky amino acids, yielding 4a, 4c and 4e. The less bulky 4b and 4d gave 4.5 and 20 regioselection Nα/Nℇ amidation ratios. A mechanistical rationalization for these selectivities is discussed.

  可以使用异丁基氯甲酸酯（方法A）或N,N-双（2-氧代-3-噁唑啉基）磷酰氯（BOP-Cl）（方法B）分别选择性地实现赖氨酸（2）的Nα或Nε参与的肽键形成。按照方法A进行的酰胺化反应能够高产率地得到二肽3a-e，不受所用氨基酸的影响。在方法B中，Nα酰胺化反应特别倾向于与体积较大的氨基酸反应，生成4a、4c和4e。体积较小的4b和4d则分别得到4.5和20的Nα/Nε酰胺化选择比。本文讨论了这些选择性的机制解释。
• Highly Enantioselective Ruthenium-Catalyzed Reduction of Ketones Employing Readily Available Peptide Ligands
  作者：Anders Bøgevig、Isidro M. Pastor、Hans Adolfsson

  DOI：10.1002/chem.200305553

  日期：2004.1.5

  Highly efficient and selective catalysts for the asymmetric reduction of aryl alkyl ketones under hydrogen-transfer conditions (2-propanol) were obtained by combining a novel class of pseudo-dipeptide ligands with [[RuCl(2)(p-cymene)](2)]. A library of 36 dipeptide-like ligands was prepared from N-Boc-protected alpha-amino acids and the enantiomers of 2-amino-1-phenylethanol and 1-amino-2-propanol

  通过将新型伪二肽配体与[[RuCl（2）（p-cymene）]（2 ）]。由N-Boc保护的α-氨基酸和2-氨基-1-苯基乙醇和1-氨基-2-丙醇的对映异构体制备了36种二肽样配体的文库。用苯乙酮的还原来评估催化剂库，并且用几种新型催化剂获得了1-苯基乙醇的优异对映选择性。发现基于N-Boc-L-丙氨酸和（S）-1-氨基-2-丙醇（配体A-（S）-4）的组合的配体特别有效。当该配体的原位形成的钌络合物用作各种芳基烷基酮的氢转移反应的催化剂时，
• Solution-phase synthesis of novel seven-membered cyclic dipeptides containing α- and β-amino acids
  作者：Erika Jiménez-González、C. Gabriela Ávila-Ortiz、Rodrigo González-Olvera、Jorge Vargas-Caporali、Georges Dewynter、Eusebio Juaristi

  DOI：10.1016/j.tet.2012.08.050

  日期：2012.11

  for the preparation of seven-membered cyclic α,β-dipeptides is described. Following coupling of N-protected α-amino acids with N-substituted β-amino acid tert-butyl esters, that affords linear α,β-dipeptides, the protecting groups at the terminal functionalities were removed and the open-chain dipeptides were cyclized with phenylphosphonic dichloride, PhP(O)Cl2, to give the desired cyclic α,β-dipeptides

  描述了一种方便的合成方法，用于制备七元环状α，β-二肽。N-保护的α-氨基酸与N-取代的β-氨基酸叔丁酯偶联后，得到线性的α，β-二肽，末端官能团上的保护基被除去，开环二肽用苯基膦二氯化物PhP（O）Cl 2，以良好的收率得到所需的环状α，β-二肽。NMR研究，X射线衍射分析和DFT计算为这些环状二肽在溶液，固态和气相中所采用的构象提供了证据。
• Amino Acids and Peptides. XLIX. Synthesis of .GAMMA.-2-Adamantylglutamate and Its Evaluation for Peptide Synthesis.
  作者：Yoshio OKADA、Yu MU

  DOI：10.1248/cpb.45.88

  日期：——

  2-Adamantyl ester was examined for the selective protection of the γ-carboxyl function of the Glu residue, with the aim of preventing side reactions during peptide synthesis and increasing the solubility in organic solvents of peptide intermediates containing the Glu residue. Z-Glu(O-2-Ada)-OBzl was synthesized from Z-Glu-OBzl and admantan-2-ol with the aid of dicyclohexylcarbodiimide (DCC) and 4-N, N-dimethylaminopyridine (DMAP) in AcOEt. The 2-adamantyl ester group was stable to TFA, 20% piperidine/DMF and 10% Et3N/DMF up to 24 h and was easily removed by MSA, 1 M TFMSA-thioanisole in TFA, and HF. Therefore, H-Glu-(O-2-Ada)-OH could be applied for peptide synthesis in both solution and solid phase methods in combination with a Boc or Fmoc group as the Nα-protecting group. Boc-Glu(O-2-Ada)-OH was successfully employed for the synthesis of Bz-Ile-Glu-Gly-Arg-CH2Cl, an irreversible inhibitor of factor Xa.

  2-亚氟烷酯被用于选择性保护谷氨酸残基的γ-羧基功能，以防止在肽合成过程中发生副反应，并提高含有谷氨酸残基的肽中间体在有机溶剂中的溶解度。从Z-Glu-OBzl和二氟烷醇在醋酸乙酯中通过二环己基碳二亚胺（DCC）和4-N,N-二甲基氨基吡啶（DMAP）的帮助下合成了Z-Glu(O-2-Ada)-OBzl。2-亚氟烷酯基团在TFA、20%哌啶/DMF和10% Et3N/DMF中稳定长达24小时，并且可以通过MSA、1 M TFMSA-硫醚醇和HF轻松去除。因此，H-Glu-(O-2-Ada)-OH可以应用于肽合成，无论是在溶液法还是固相法中，并结合Boc或FMoc基团作为Nα保护基团。Boc-Glu(O-2-Ada)-OH成功应用于合成Bz-Ile-Glu-Gly-Arg-CH2Cl，这是Xa因子的不可逆抑制剂。