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使用高效液相色谱法优化含氟两亲物的分离

Optimize the Separation of Fluorinated Amphiles Using High-Performance Liquid Chromatography.

作者信息

Xia Guiquan, Li Yuqi, Li Yu, Li Xuefei, Zhang Hua, Yu Yihua Bruce, Jiang Zhong-Xing

机构信息

Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education, and Wuhan University School of Pharmaceutical Sciences, Wuhan 430071, P. R. China.

Department of Pharmaceutical Sciences, University of Maryland, Baltimore, MD 21201, United States.

出版信息

J Fluor Chem. 2014 Sep 1;164:39-42. doi: 10.1016/j.jfluchem.2014.06.005.

DOI:10.1016/j.jfluchem.2014.06.005
PMID:25147409
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4136531/
Abstract

Using the set of fluorinated amphiles that contain the same fluorocarbon moiety but differ in their fluorine content percentage F% (25-45%), the optimal condition for a F%-based separation of these analytes using reverse-phase chromatography was explored. It is found that optimal separation can be achieved by pairing a regular reverse-phase column (such as C8) with a fluorinated eluent (such as trifluoroethanol). Separation is further improved at higher chromatographic temperature with baseline separation achieved at 45°C. This result indicates that the separation of fluorocarbon-tagged molecules can be based on the fluorine content percentage rather than the number of fluorine atoms.

摘要

使用一组含有相同碳氟化合物部分但氟含量百分比F%(25 - 45%)不同的氟化两亲物,探索了使用反相色谱基于F%分离这些分析物的最佳条件。发现通过将常规反相柱(如C8)与氟化洗脱剂(如三氟乙醇)配对可实现最佳分离。在较高的色谱温度下分离进一步改善,在45°C时实现基线分离。该结果表明,碳氟化合物标记分子的分离可基于氟含量百分比而非氟原子数量。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/099a/4136531/702fc78700fd/nihms611343f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/099a/4136531/8744e4e2a347/nihms611343f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/099a/4136531/702fc78700fd/nihms611343f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/099a/4136531/8744e4e2a347/nihms611343f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/099a/4136531/702fc78700fd/nihms611343f2.jpg

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1
Optimize the Separation of Fluorinated Amphiles Using High-Performance Liquid Chromatography.使用高效液相色谱法优化含氟两亲物的分离
J Fluor Chem. 2014 Sep 1;164:39-42. doi: 10.1016/j.jfluchem.2014.06.005.
2
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本文引用的文献

1
The Effect of Column and Eluent Fluorination on the Retention and Separation of non-Fluorinated Amino Acids and Proteins by HPLC.柱和洗脱液氟化对高效液相色谱法分离非氟化氨基酸和蛋白质的保留及分离效果的影响
J Fluor Chem. 2011 Feb 1;132(2):114-122. doi: 10.1016/j.jfluchem.2010.12.005.
2
Separation of Fluorinated Amino Acids and Oligopeptides from their Non-fluorinated Counterparts using High-performance Liquid Chromatography.使用高效液相色谱法从非氟化对应物中分离氟化氨基酸和寡肽。
J Fluor Chem. 2010 Mar 1;131(3):439-445. doi: 10.1016/j.jfluchem.2009.11.025.
3
Fluorous mixture synthesis of asymmetric dendrimers.氟相混合物合成手性树枝状大分子。
J Org Chem. 2010 Mar 19;75(6):2044-9. doi: 10.1021/jo100102a.
4
Symmetry-guided design and fluorous synthesis of a stable and rapidly excreted imaging tracer for (19)F MRI.用于(19)F磁共振成像的稳定且快速排泄的成像示踪剂的对称引导设计与氟相合成
Angew Chem Int Ed Engl. 2009;48(26):4755-8. doi: 10.1002/anie.200901005.
5
Sense and nonsense of high-temperature liquid chromatography.高效液相色谱法的合理与不合理之处
J Chromatogr A. 2009 Jan 23;1216(4):642-58. doi: 10.1016/j.chroma.2008.11.079. Epub 2008 Dec 3.
6
Confirmation of the stereostructure of (+)-cytostatin by fluorous mixture synthesis of four candidate stereoisomers.通过四种候选立体异构体的氟代混合物合成对(+)-细胞抑制素立体结构的确认。
Angew Chem Int Ed Engl. 2008;47(6):1130-3. doi: 10.1002/anie.200704893.
7
Fluorous catalysis under homogeneous conditions without fluorous solvents: a "greener" catalyst recycling protocol based upon temperature-dependent solubilities and liquid/solid phase separation.无氟溶剂的均相条件下的氟催化:基于温度依赖性溶解度和液/固相分离的“更绿色”催化剂循环方案。
J Am Chem Soc. 2003 May 14;125(19):5861-72. doi: 10.1021/ja029241s.
8
Solution-phase preparation of a 560-compound library of individual pure mappicine analogues by fluorous mixture synthesis.通过氟代混合物合成法在溶液相中制备由560种单个纯马皮辛类似物组成的化合物库。
J Am Chem Soc. 2002 Sep 4;124(35):10443-50. doi: 10.1021/ja026947d.
9
Simultaneous preparation of four truncated analogues of discodermolide by fluorous mixture synthesis.
Org Lett. 2002 Jun 27;4(13):2233-5. doi: 10.1021/ol026084t.
10
Unique selectivity of perfluorinated stationary phases with 2,2,2-trifluoroethanol as organic mobile phase modifier.以2,2,2-三氟乙醇为有机流动相改性剂的全氟固定相的独特选择性。
J Chromatogr A. 2001 Nov 9;933(1-2):73-81. doi: 10.1016/s0021-9673(01)01254-7.