Fmoc-Tyr-Gly-Gly-Phe-Leu-OH | 149207-52-3

• 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: Fmoc-Tyr-Gly-Gly-Phe-Leu-OH
• 英文别名: (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoic acid
• CAS: 149207-52-3
• 化学式: C₄₃H₄₇N₅O₉
• 分子量: 777.874
• InChiKey: NWLLDTOXWQVPAY-FSEITFBQSA-N

物化性质

• 沸点：
  1156.5±65.0 °C(predicted)
• 密度：
  1.292±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  57
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  212
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Fmoc-Tyr-Gly-Gly-Phe-Leu-OH 生成 (S)-2-[(S)-2-(2-{2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(4-hydroxy-3,5-diiodo-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid
  参考文献：
  名称：

  First aromatic electrophilic iodination reaction on the solid-phase: Iodination of bioactive peptides

  摘要：

  Direct iodination of Tyr residues of peptides anchored on solid supports was accomplished, for the first time, by aromatic electrophilic attack of iodonium ions provided by the IPy2BF4 reagent. Compatibility studies of the iodination with routine solid-phase synthesis protocols are reported. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01604-9
• 作为产物：
  描述：

  Leu-enkephalin 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 以 水 、 丙酮 为溶剂， 以95%的产率得到Fmoc-Tyr-Gly-Gly-Phe-Leu-OH
  参考文献：
  名称：

  Synthesis of a new molecular carrier: N-(Leu-enkephalin)yl 6-amido-6-deoxy-cyclomaltoheptaose

  摘要：

  The synthesis of N-(Leu-enkephalin)yl 6-amido-6-deoxy-cyclomaltoheptaose has been performed in high yield. The final derivative has been characterized by proton NMR in terms of chemical structure and inclusion properties and represents a new class of target-directed transporters.

  DOI：

  10.1016/s0040-4039(00)60440-9

文献信息

• Thiophene Backbone Amide Linkers, a New Class of Easily Prepared and Highly Acid-Labile Linkers for Solid-Phase Synthesis
  作者：Mikkel Jessing、Malene Brandt、Knud J. Jensen、Jørn B. Christensen、Ulrik Boas

  DOI：10.1021/jo060687r

  日期：2006.9.1

  bond was performed by a chemoselective Negishi coupling without transient protection of the aldehyde group to provide the T-BAL1 handle. Introduction via a thioether linkage was performed by a facile nucleophilic aromatic substitution between the brominated EDOT aldehyde and unprotected mercapto acids to provide T-BAL2 and T-BAL3 handles. The minimal use of protecting groups gave the corresponding linker

  固相合成对于小分子和生物聚合物合成极为重要。固相合成完成后释放含酰胺产物的接头（手柄）被广泛使用。在这里，我们介绍了基于3,4-乙二氧基噻吩（EDOT）的一类新的高度酸不稳定的骨架酰胺连接基（BAL手柄），我们将其称为T-BAL。这些噻吩接头是通过三个方便的步骤从市售EDOT合成的。在连接子设计中，间隔基通过碳-碳键或硫醚键引入到EDOT核中。通过C-C键引入间隔基是通过化学选择性的Negishi偶联进行的，没有对醛基的瞬态保护，以提供T-BAL1手柄。通过硫醚键的引入是通过在溴化的EDOT醛和未保护的巯基酸之间进行轻松的亲核芳族取代来完成的，以提供T-BAL2和T-BAL3提手。保护基团的最少使用以很少的合成步骤并以良好的收率得到了相应的接头分子。在将接头锚定到聚合物载体上之后，通过还原胺化来引入第一氨基酸，得到仲胺。随后用对称氨基酸酸酐对仲胺进行酰化，导致在手柄和生长中的底物（例如肽链
• Cleaving protected peptides from 2-chlorotrityl chloride resin. Moving away from dichloromethane
  作者：Mahama Alhassan、Othman Al Musaimi、Jonathan M. Collins、Fernando Albericio、Beatriz G. de la Torre

  DOI：10.1039/d0gc00834f

  日期：——

  substitution of the hazardous solvents most widely used in solid-phase peptide synthesis, namely DMF, NMP, DCM, DEE, among others, by several much less hazardous solvents. Indeed, greener alternatives have been found for almost all steps of the process, with the exception of the cleavage of protected peptides from 2-chlorotrityl chloride resin. Here, after careful screening of several of the so-called green

  近年来，各个研究小组的工作已允许用几种危险性低得多的溶剂代替固相肽合成中最广泛使用的危险溶剂，即DMF，NMP，DCM，DEE等。实际上，除了从2-氯三苯甲基氯树脂切割保护的肽以外，几乎在该方法的所有步骤中都发现了更绿色的替代品。在这里，仔细筛选了几种所谓的绿色溶剂后，我们提出了在苯甲醚或1,3-二甲氧基苯中的2％TFA作为裂解步骤的最佳选择。这些溶剂与DCM相比，沸点更高，因此可以制备保护性肽，且过早去除最不稳定的保护基（例如His的Trt）的风险较小。
• Development of an Intein-Inspired Amide Cleavage Chemical Device
  作者：Chiaki Komiya、Keisuke Aihara、Ko Morishita、Hao Ding、Tsubasa Inokuma、Akira Shigenaga、Akira Otaka

  DOI：10.1021/acs.joc.5b02399

  日期：2016.1.15

  A photoresponsive amide cleavage device was developed based on the asparagine imidation-mediated cleavage of peptide bonds during intein-mediated protein splicing. The chemical environment of the protein splicing process was mimicked by the incorporation of geminal dimethyl groups and a secondary amine unit in asparagine scaffold. Furthermore, the resulting photoresponsive device could induce the phototriggered cleavage of an amide bond by the protection of the secondary amine unit with an o-nitrobenzyloxycarbonyl group.
• First aromatic electrophilic iodination reaction on the solid-phase: Iodination of bioactive peptides
  作者：Gemma Arsequell、Gemma Espuña、Gregorio Valencia、José Barluenga、Raquel Pérez Carlón、JoséM. González

  DOI：10.1016/s0040-4039(98)01604-9

  日期：1998.10

  Direct iodination of Tyr residues of peptides anchored on solid supports was accomplished, for the first time, by aromatic electrophilic attack of iodonium ions provided by the IPy2BF4 reagent. Compatibility studies of the iodination with routine solid-phase synthesis protocols are reported. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Synthesis of a new molecular carrier: N-(Leu-enkephalin)yl 6-amido-6-deoxy-cyclomaltoheptaose
  作者：Florence Djedaïni-Pilard、Jacques Désalos、Bruno Perly

  DOI：10.1016/s0040-4039(00)60440-9

  日期：1993.4

  The synthesis of N-(Leu-enkephalin)yl 6-amido-6-deoxy-cyclomaltoheptaose has been performed in high yield. The final derivative has been characterized by proton NMR in terms of chemical structure and inclusion properties and represents a new class of target-directed transporters.