Fmoc-Tyr(Trt)-OH | 133180-02-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Fmoc-Tyr(Trt)-OH
• 英文别名: L-Tyrosine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-(triphenylmethyl)-；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-trityloxyphenyl)propanoic acid
• CAS: 133180-02-6
• 化学式: C₄₃H₃₅NO₅
• 分子量: 645.755
• InChiKey: HNJXYCFXVDHYKW-FAIXQHPJSA-N

物化性质

• 沸点：
  825.5±65.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Fmoc-Tyr(Trt)-OH 在 哌啶 作用下， 生成 O-trityl-Tyr
  参考文献：
  名称：

  4-Toluenesulfonylureido derivatives of amines, amino acids and dipeptides: a novel class of potential antitumor agents

  摘要：

  The screening of a series of arylsulfonylureido derivatives of amines (such as histamine, or dopamine), aliphatic/aromatic amino acids (such as Gly, beta -Ala, Val, Lys, Arg, Phe, Tyr, DOPA, etc.) and dipeptides (such as GlyGly, beta -AlaHis) led to the identification of three derivatives that possess tumor growth inhibitory properties against several leukemia, non-small cell lung, ovarian, melanoma, colon, CNS, renal, and breast cancer cell lines in vitro. The new derivatives were prepared by reaction of 4-toluenesulfonyl isocyanate with (protected) amines, amino acids or dipeptides. The mechanism of antitumor action with these new derivatives is not known at the moment but it may imply uncoupling of mitochondria, as for the structurally related diarylsulfonylurea sulofenur, an investigational anticancer agent. (C) 2000 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0928-0987(00)00122-6
• 作为产物：
  描述：

  Trt-Tyr-OH*Et3N 在 4-二甲氨基吡啶 、 sodium hydroxide 、 2,2,2-三氟乙醇 、 溶剂黄146 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 Fmoc-Tyr(Trt)-OH
  参考文献：
  名称：

  N-Fmoc-O-Trt-hydroxyaminosäurenzur“固相”合成冯肽

  摘要：

  The preparation of the N-Fmoc-O-Trt derivatives of serine, threonine and tyrosine is described. Their usefulness in peptide synthesis has been determined in the successful solid phase preparation of the partially protected ACTH (fragment 1-10) and peptide T 12. The latter, having six hydroxy amino acid side chains protected with Trt groups, can be quantitatively cleaved from the applied 2-chlorotrityl resin with simultaneous side chain deprotection.

  DOI：

  10.1016/s0040-4039(00)79471-8

文献信息

• A Dimethyl Ketal-Protected Benzoin-Based Linker Suitable for Photolytic Release of Unprotected Peptides
  作者：Nataliya Chumachenko、Yehor Novikov、Richard K. Shoemaker、Shelley D. Copley

  DOI：10.1021/jo2017263

  日期：2011.11.18

  Photolabile 3',5'-dimethoxybenzoin-based linkers are advantageous for a variety of solid-phase synthetic procedures and manipulations of biomolecules because UV irradiation in aqueous media provides fast and essentially quantitative release of tethered molecules, while generating unreactive side products. Practical applications of previously reported linkers are compromised to some extent by the 1,3-dithiane protection of the benzoin carbonyl group and the lengthy synthesis. We have extended the group of photocleavable 3',5'-dimethoxybenzoin-based linkers by designing and synthesizing a linker in which the carbonyl group is protected as a dimethyl ketal. This protection is compatible with commonly used esterification and amide bond formation techniques, including the Fmoc/tBu strategy for solid phase peptide synthesis, is stable under mild acidic conditions, and can be quantitatively removed in <5 min by 3% TFA in dichloromethane. Irradiation of beads carrying peptides attached to the linker at 350 nm in aqueous or partially aqueous media affords >90% release after 30 min. The linker was synthesized from commercially available starting materials in five steps with an overall yield of 40% and without any column chromatography purification. Additionally, we developed a route to a dithiane-protected linker that requires only two steps and proceeds in 65% yield, a significant improvement over previous synthetic routes.
• Preferential binding to DNA sequences of peptides related to a novel XPRK motif
  作者：Chia-Hung Yang、Ping-Jen Chou、Zhen Long Luo、I Chun Chou、Jung-Cheng Chang、Chien-Chung Cheng、Christopher R.H Martin、Michael.J Waring、Leung Sheh

  DOI：10.1016/s0968-0896(03)00279-7

  日期：2003.7

  Two dodecapeptide amides: (WPRK)(3)NH2 [WR-12] and (YPRK)(3)NH2 [YR-12], and a 30-mer polypeptide amide (SP-30) were synthesized by solid-phase peptide methodology. DNase I footprinting studies on a 117-mer DNA showed that WR-12 and YR-12 bind selectively to DNA sequences in a manner similar to SP-30 which has a repeating SPK(R)K sequence. The most distinctive blockages seen with all three peptides occur at positions 26-30, 21-24 and 38-45 around sequences 5'-GAATT-3', 5'-TAAT-3' and 5'-AAAACGAC-3', respectively. However, it appears that YR-12 is better able to extend its recognition site to include CG pairs than is SP-30. At low concentrations YR-12 was able to induce enhanced rates of DNase I cleavage at regions surrounding some of its binding sites. To obtain further quantitative data supplementary to the footprinting work, equilibrium binding experiments were performed in which the binding of the two peptides to six decanucleotide duplexes was compared. Scatchard analyses indicated that WR-12 may be more selective for oligomers containing runs of consecutive purines or pyrimidines. On the other hand, YR-12 binds better to d(CTTAGACGTC)- d(GACGTCTAAG) than to the other oligomer duplexes, denoting selectivity for evenly distributed C/G and A/T sequences. (C) 2003 Elsevier Science Ltd. All rights reserved.
• 4-Toluenesulfonylureido derivatives of amines, amino acids and dipeptides: a novel class of potential antitumor agents
  作者：Antonio Mastrolorenzo、Andrea Scozzafava、Claudiu T. Supuran

  DOI：10.1016/s0928-0987(00)00122-6

  日期：2000.10

  The screening of a series of arylsulfonylureido derivatives of amines (such as histamine, or dopamine), aliphatic/aromatic amino acids (such as Gly, beta -Ala, Val, Lys, Arg, Phe, Tyr, DOPA, etc.) and dipeptides (such as GlyGly, beta -AlaHis) led to the identification of three derivatives that possess tumor growth inhibitory properties against several leukemia, non-small cell lung, ovarian, melanoma, colon, CNS, renal, and breast cancer cell lines in vitro. The new derivatives were prepared by reaction of 4-toluenesulfonyl isocyanate with (protected) amines, amino acids or dipeptides. The mechanism of antitumor action with these new derivatives is not known at the moment but it may imply uncoupling of mitochondria, as for the structurally related diarylsulfonylurea sulofenur, an investigational anticancer agent. (C) 2000 Elsevier Science B.V. All rights reserved.
• Darstellung und einsatz von N-Fmoc-O-Trt-hydroxyaminosäuren zur “solid phase” synthese von peptiden
  作者：Kleomenis Barlos、Dimitrios Gatos、Sophia Koutsogianni、Wolfram Schäfer、George Stavropoulos、Yao Wenging

  DOI：10.1016/s0040-4039(00)79471-8

  日期：1991.1

  The preparation of the N-Fmoc-O-Trt derivatives of serine, threonine and tyrosine is described. Their usefulness in peptide synthesis has been determined in the successful solid phase preparation of the partially protected ACTH (fragment 1-10) and peptide T 12. The latter, having six hydroxy amino acid side chains protected with Trt groups, can be quantitatively cleaved from the applied 2-chlorotrityl resin with simultaneous side chain deprotection.