N-tert-butoxycarbonyl-L-phenylalanine-L-phenylalanine-glycine | 82816-76-0

• 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: N-tert-butoxycarbonyl-L-phenylalanine-L-phenylalanine-glycine
• 英文别名: Boc-Phe-Phe-Gly-OH；Boc-Phe-Phe-Gly；Boc-L-Phe-L-Phe-Gly-OH；2-[[(2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]acetic acid
• CAS: 82816-76-0
• 化学式: C₂₅H₃₁N₃O₆
• mdl: MFCD00057826
• 分子量: 469.538
• InChiKey: OJBXRIGCBKNSQC-PMACEKPBSA-N

物化性质

• 熔点：
  135-137 °C
• 沸点：
  793.4±60.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-L-phenylalanine-L-phenylalanine-glycine 在 N-甲基吗啉 、 盐酸 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 反应 27.25h， 生成 HCl*Phe-Phe-Gly-Leu-Met-NH2
  参考文献：
  名称：

  Conformationally restricted C-terminal peptides of substance P. Synthesis, mass spectral analysis and pharmacological properties

  摘要：

  Four cyclic analogues of the C-terminal hepta- or hexapeptide of substance P were prepared by the solution method. The cyclizations were obtained by substituting with cysteine the residues normally present in positions 5 or 6 or 11 of substance P and by subsequent disulfide bond formation. The final products were identified by ordinary analytical procedures and advanced mass spectroscopy. The biological activities were determined on three bioassays: the guinea pig ileum, the guinea pig trachea and the rabbit mesenteric vein. Results obtained with these assays indicate that all peptides with a disulfide bridgehead in position 11 are inactive and that a cycle between positions 5 and 6 already strongly reduces the biological activity. The acyclic precursors containing thiol protection groups display weak biological activities. These results further underline the importance of the side chain in position 11 of substance P and suggest that optimal biological activities may require a linear peptide sequence.

  DOI：

  10.1021/jm00148a029
• 作为产物：
  描述：

  (S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropanoate 在 盐酸 、 一水合肼 、 三乙胺 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 反应 96.25h， 生成 N-tert-butoxycarbonyl-L-phenylalanine-L-phenylalanine-glycine
  参考文献：
  名称：

  Koziolkiewicz, Wiktor; Wasiak, Tadeusz; Janecka, Anna, Polish Journal of Chemistry, 1985, vol. 59, # 7-9, p. 819 - 826

  摘要：

  DOI：

文献信息

• Facile and Mild Synthesis of Linear and Cyclic Peptides via Thioesters
  作者：Paola Agrigento、Fernando Albericio、Sylvie Chamoin、Isabelle Dacquignies、Halil Koc、Martin Eberle

  DOI：10.1021/ol501669n

  日期：2014.8.1

  Thioester-mediated peptide bond formation has recently garnered a lot of attention, most notably in its relevance to condensation of large peptide fragments. Herein, a simple and general ligation method for the preparation of linear and cyclic peptides, starting from peptide thioester, mainly p-chlorophenyl, precursors is reported. The inherent advantages of this method are the low epimerization, reduced

  硫酯介导的肽键形成近来引起了很多关注，尤其是与大肽片段缩合有关。在本文中，报道了一种简单且通用的制备线性和环状肽的方法，该方法从肽硫酯，主要是对氯苯基前体开始。该方法的固有优点是低差向异构化，减少的二聚化，使用温和的反应条件以及消除了多余的偶联剂。
• Hydroxymethyl Salicylaldehyde Auxiliary for a Glycine-Dependent Amide-Forming Ligation
  作者：Marianne Fouché、Florence Masse、Hans-Jörg Roth

  DOI：10.1021/acs.orglett.5b02350

  日期：2015.10.16

  A new amide-forming ligation that requires a glycine or a primary amine at the linkage site is described herein. The distinguishing feature of this ligation is its reliance on an O-hydroxymethyl salicylaldehyde ester at the C-terminus which allows, via an N,O-acetal intermediate, the formation of a native peptide bond.

  本文描述了在连接位点需要甘氨酸或伯胺的新的酰胺形成连接。这种连接的显着特征是它依赖于在C-末端的O-羟甲基水杨醛酯，它允许通过N，O-乙缩醛中间体形成天然的肽键。
• Multigram-Scale Synthesis of Short Peptides via a Simplified Repetitive Solution-Phase Procedure
  作者：Célia Meneses、Sarah L. Nicoll、Laurent Trembleau

  DOI：10.1021/jo902116p

  日期：2010.2.5

  A rapid repetitive solution-phase synthesis of peptides is described. The procedure involves coupling of amino acids and peptide acids, instead of the usual amino esters and peptide esters, to slight excesses of pentafluorophenyl active esters in a THF/water solvent mixture. Due to their poor solubility, peptide acid intermediates are easily isolated in high purity by acidification under controlled

  描述了肽的快速重复溶液相合成。该方法涉及在THF /水溶剂混合物中，将氨基酸和肽酸（而不是通常的氨基酯和肽酯）偶联到稍微过量的五氟苯基活性酯上。由于它们的溶解性差，因此容易通过在受控条件下酸化并通过选择性萃取除去过量的活性酯，以高纯度分离出肽酸中间体。与现代的重复溶液阶段肽合成程序相反，我们的方法不需要费时的中和反应，并且显着减少了获得肽中间体所需的操作单元数。快速合成疏水性和亲水性短肽证明了该方法的有效性，
• Isolation, structure and synthesis of mahafacyclin B, a cyclic heptapeptide from the latex of Jatropha mahafalensis
  作者：Carine Baraguey、Alain Blond、Florine Cavelier、Jean-Louis Pousset、Bernard Bodo、Catherine Auvin-Guette

  DOI：10.1039/b008538n

  日期：——

  Mahafacyclin B is a cyclic heptapeptide with antimalarial activity isolated from the latex of Jatropha mahafalensis. The structure is elucidated by chemical degradation, tandem mass spectrometry, homo- and heteronuclear NMR experiments, and confirmed by synthesis.

  大法环素B是一种具有抗疟活性的环七肽，从麻风树（Jatropha mahafalensis）的乳汁中分离得到。其结构通过化学降解、串联质谱、同核和异核NMR实验阐明，并通过合成加以验证。
• Syntheses of Cyclic Octapeptides and Mediation by Them of Selective Transport, Including Enantiomer Recognition, through an Organic Liquid Membrane.
  作者：Hiromi KATAOKA、Tomoko HANAWA、Toyoshi KATAGI

  DOI：10.1248/cpb.40.570

  日期：——

  Cyclic octapeptides (1-4) having analogous amino acid sequences were synthesized from the corresponding linear peptides using a conventional sulution-phase method. The cyclization was performed by the EDCI/HOBt procedure using an equimolar mixture of alkaline metal cations at a high dilution (concentration of linear peptide : 1.2 mM). The selective transport of amino acid methyl ester and amine salts through an organic liquid membrane mediated by the synthetic cyclic octapeptides and the enantiomer recognition properties in the transport of racemic Phe-OMe salt were examined. The cyclic octapeptides transported D-Phe-OMe salt more efficiently than other guest salts.

  采用传统的稀释法从相应的线性肽合成了具有类似氨基酸序列的环状八肽（1-4）。环化采用 EDCI/HOBt 程序，使用碱金属阳离子等摩尔混合物高稀释（线性肽浓度：1.2 mM）。研究了合成环状八肽介导的氨基酸甲酯和胺盐通过有机液体膜的选择性转运以及外消旋 Phe-OMe 盐转运过程中的对映体识别特性。环状八肽转运 D-Phe-Ome盐的效率高于其他客体盐。