CAS: 136590-09-5; N-Fmoc-3-Nitro-L-Tyrosine

该化合物是L-tyrosine受保护的衍生物,其特点是α-氨基位置的Fmoc(9-氟甲基苯氧碳基)组和芳香环三处位置的硝化物组.该化合物主要用于固相丙酸合成(SPS),作为将硝化硫残留物引入peptide序列的一个构件.Fmoc组提供正方位保护,在温和的基本条件下允许有选择地取消保护,而硝化物可以作为进一步功能化或光谱探测器的先兆,其高度纯度和稳定性使其适合精确的peptide变异,特别是在涉及红氧化活性硫酸衍生物或转基因改变的研究中.

英文名称N-Fmoc-3-Nitro-L-Tyrosine
中文名称Fmoc-3-硝基-L-酪氨酸
IUPAC名称(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxy-3-nitrophenyl)propanoic acid
其它别名Fmoc-Tyr(3-No2)-Oh; Fmoc-Phe(P-Oh,M-No2)-Oh; Fmoc-L-Tyr(3-No2)-Oh; Fmoc-M-Nitro-P-Hydroxy-Phe-Oh; Fmoc-M-Nitro-Tyr-Oh; 2-[[(2-Ethylidene-3-Prop-2-Enylidene-1H-Inden-1-yl)Methoxy-Oxomethyl]Amino]-3-(4-Hydroxy-3-Nitrophenyl)Propanoic Acid; N-Alpha-(9-Fluorenylmethoxycarbonyl)-(S)-2-Amino-3-(M-Nitro-P-Hydroxy) Phenylpropanoic Acid; N-Alpha-(9-Fluorenylmethyloxycarbonyl)-L-3-Nitrotyrosine
CAS编号136590-09-5
MFCD编号:MFCD00171383
EINECS号:000-000-0
分子式:C24H20N2O7
分子量:448.42
产品CID: 568724
产品分类有机原料→生命科学→氨基酸及其衍生物→酪氨酸及其衍生物

相似结构搜索
InChIKey: JZUZJVFERQWLNC-FQEVSTJZSA-N
InChI=1S/C24H20N2O7/c27-22-10-9-14(12-21(22)26(31)32)11-20(23(28)29)25-24(30)33-13-19-17-7-3-1-5-15(17)16-6-2-4-8-18(16)19/h1-10,12,19-20,27…
计算化学: 氢键受体数6.0氢键供体数3.0可旋转键数7.0

相似化合物

621-44-3 726181-70-0 1270301-81-9

物理性质

沸点704.4 °C at 760 mmHg
闪点379.8±32.9 °C
密度1.4±0.1 g/cm3
pKa:2.77±0.10(预测)
PSA:139.0
LogP:3.8348
折射率1.667
蒸汽压0.0±2.3 mmHg at 25°C
溶解性Soluble In Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,Etc.
敏感性如果遵照规格使用和储存则不会分解，未有已知危险反应
外观形态粉末
储存条件密封干燥,2-8°C

上下游产品

合成工艺路线路线简述

(S)-3-(4-Hydroxyphenyl)-2-[(Ethoxycarbonyl)Amino]-1-Propanoic Acid Methyl Ester置于盐酸,氢氧化钾,Sodium Nitrate,Sodium Carbonate,Lanthanum(III) Nitrate体系中,用 1,4-二氧六环用作溶剂,化学反应生成Fmoc-3-硝基-L-酪氨酸
参考文献:Development Of L-3-Aminotyrosine Suitably Protected For The Synthesis Of A Novel Nonphosphorylated Hexapeptide With Low-Nanomolar Grb2-Sh2 Domain-Binding Affinity
标题:Development Of L-3-Aminotyrosine Suitably Protected For The Synthesis Of A Novel Nonphosphorylated Hexapeptide With Low-Nanomolar Grb2-Sh2 Domain-Binding Affinity
摘要:Synthesis Of Orthogonally Protected (2S)-2-Amino-3-(3-Amino-4-Hydroxy-Phenyl)-Propionic Acid (10) Suitable For Solid Phase Peptide Synthesis And Its First Use For The Preparation Of Nonphosphorylated Grb2-Sh2 Domain Antagonists (4A-C) Are Reported. The 3-Aminotyrosine Containing Sulfoxide-Cyclized Hexapeptide (4B) Exhibited Potent Grb2-Sh2 Domain Binding Affinity With Ic50 = 50 Nm Which Represents The Highest Affinity Yet Reported For A Peptide Inhibitor Against Grb2-Sh2 Domain With Only Six Residues Free Of Phosphotyrosine Or Phosphotyrosine Mimics. This Potent Small Peptidomimetic 4B May Be Representative Of A New Class Of Therapeutically Relevant Grb2-Sh2 Domain-Directed Agents,And Acts As A Chemotherapeutic Lead For The Treatment Of Erbb2-Related Cancers. (C) 2004 Elsevier Ltd. All Rights Reserved.
Doi:10.1016/j.Bmcl.2004.03.103