N^α-fluoren-9-ylmethyloxycarbonyl-L-phenylalanyl-L-threonine | 87720-57-8

• 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^α-fluoren-9-ylmethyloxycarbonyl-L-phenylalanyl-L-threonine
• 英文别名: Fmoc-Phe-Thr-OH；Fmoc-Phe-Thr；N-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-L-phenylalanyl-L-threonine；(2S,3R)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoyl]amino]-3-hydroxybutanoic acid
• CAS: 87720-57-8
• 化学式: C₂₈H₂₈N₂O₆
• 分子量: 488.54
• InChiKey: YKWIITBFJOUZTF-XATISFHKSA-N

物化性质

• 沸点：
  800.1±65.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Fmoc-Phe-benzotriazolyl ester 在 phosphate buffer 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 4.0h， 生成 N^α-fluoren-9-ylmethyloxycarbonyl-L-phenylalanyl-L-threonine
  参考文献：
  名称：

  Chemo-Enzymatic Synthesis of Fmoc-Peptide Fragments

  摘要：

  Optically pure Fmoc-peptide fragments have been prepared via dicyclohexylcarbodiimide coupling of N-protected amino acids with amino acid esters, followed by enzyme-catalyzed ester hydrolysis by alcalase with a high concentration of organic solvent in a high yield.

  DOI：

  10.1080/00397919208055416

文献信息

• Phase-transfer reagents as C-terminal protecting groups; facile incorporation of free amino acids or peptides into peptide sequences
  作者：Shui-Tein Chen、Kung-Tsung Wang

  DOI：10.1039/c39900001045

  日期：——

  Phase-transfer reagents (basic, neutral, and acidic) can effect temporary protection of carboxy groups by salt formation in C-terminal free amino acids or peptides during peptide synthesis; the use of acidic or neutral phase-transfer reagents as the C-terminal protecting group will not affect the nucleophilicity of the amino group of the salts thus prepared in an organic solvent.

  相转移试剂（碱性，中性和酸性）可通过在肽合成过程中在C端游离氨基酸或肽中形成盐来暂时保护羧基。使用酸性或中性相转移试剂作为C-末端保护基不会影响在有机溶剂中如此制得的盐的氨基的亲核性。
• Synthesis of [4,5-dehydroLeu2]- and [3,4-dehydropro6]-locust adipokinetic hormone
  作者：Paul M. Hardy、Paul W. Sheppard

  DOI：10.1039/p19830000723

  日期：——

  The syntheses of [4,5-dehydroLeu2]- and [3,4-dehydroPro6]-locust adipokinetic hormone (LAKH) by the coupling of N-terminal hexapeptides prepared by the solid-phase method with a common C-terminal tetrapeptide synthesised in solution is described. At a dose level of 20 pmol, the former is at least as biologically active as LAKH, but the latter has only ca. 20% of the activity. Difficulties encountered

  通过固相法制备的N末端六肽与常见的C末端四肽的偶联，合成[4,5-dehydroLeu 2 ]-和[3,4-dehydroPro 6 ]-蝗脂肪动力学激素（LAKH）。描述了在溶液中合成。在剂量为20 pmol时，前者的生物活性至少与LAKH相同，而后者仅约20mg 。活动的20％。讨论了在将4，5-脱氢亮氨酸残基掺入肽中遇到的困难。
• Solid-Phase Synthesis of 1,3-Azole-Based Peptides and Peptidomimetics
  作者：Eric Biron、Jayanta Chatterjee、Horst Kessler

  DOI：10.1021/ol0607645

  日期：2006.5.1

  [graphics]We report highly efficient two-step procedures for the synthesis of 1,3-oxazole-, thiazole-, and imidazole- containing peptides on solid phase from dipeptides composed of C-terminal threonine, serine, cysteine, or diaminopropionic acid by using different cyclodehydration procedures followed or preceded by oxidation. The methods are compatible with Fmoc solid-phase peptide synthesis conditions and with N-Fmoc, N-Boc, N-Cbz, and N-Alloc protecting groups.
• CHEN, SHUI-TEIN;WANG, KUNG-TSUNG, J. CHEM. SOC. CHEM. COMMUN.,(1990) N5, C. 1045-1047
  作者：CHEN, SHUI-TEIN、WANG, KUNG-TSUNG

  DOI：——

  日期：——
• Chemo-Enzymatic Synthesis of Fmoc-Peptide Fragments
  作者：Shui-Tein Chen、Shu-Chyong Hsiao、Chung-Ho Chang、Kung-Tsung Wang

  DOI：10.1080/00397919208055416

  日期：1992.1

  Optically pure Fmoc-peptide fragments have been prepared via dicyclohexylcarbodiimide coupling of N-protected amino acids with amino acid esters, followed by enzyme-catalyzed ester hydrolysis by alcalase with a high concentration of organic solvent in a high yield.