林伯樵實驗室 (the research group of Dr. Po-Chiao Lin)

本實驗室於2014年之研究成果:A mild removal of Fmoc group using sodium azide

利用中性之溫和條件有效率進行Fmoc保護基團之移除。並成功應用於小分子及胜肽之合成

發表於:Amino Acids 2014, 46, 367.

Abstract : A mild method for effectively removing the
fluorenylmethoxycarbonyl (Fmoc) group using sodium
azide was developed. Without base, sodium azide completely
deprotected Na-Fmoc-amino acids in hours. The
solvent-dependent conditions were carefully studied and
then optimized by screening different sodium azide
amounts and reaction temperatures. A variety of Fmocprotected
amino acids containing residues masked with
different protecting groups were efficiently and selectively
deprotected by the optimized reaction. Finally, a biologically
significant hexapeptide, angiotensin IV, was successfully
synthesized by solid phase peptide synthesis
using the developed sodium azide method for all Fmoc
removals. The base-free condition provides a complement
method for Fmoc deprotection in peptide chemistry and
modern organic synthesis.

本實驗室於2014年最新研究成果發表於美國化學會有機化學期刊 The Journal of Organic Chemistry

利用一價銅催化之Dihydropyrimidinone之合成及其在beta-amino acid衍申物之合成

後續之合成應用亦正在積極開發中!

A copper(I)-catalyzed synthesis of substituted dihydropyrimidin-4-ones from propargyl amides via the formation
of ketenimine intermediate has been successfully developed; the synthesis afforded good isolated yields (80−95%). The mild
reaction conditions at room temperature allow the reaction to proceed to completion in a few hours without altering the
stereochemistry. Further, by involving a variety of reactive nucleophiles, the obtained substituted dihydropyrimidin-4-ones were
elegantly transformed into the corresponding β- and β3-amino acid analogues.

本研究工作發表於下列期刊:

J. Org. Chem. 2014, 79, 1254.

http://pubs.acs.org/doi/abs/10.1021/jo402670d 

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!  

Journals:

1. P.-H. Chou, S.-H. Chen, H.-K. Liao, P.-C. Lin, G.-R. Her, Alan C.-Y. Lai, J.-H. Chen, C.-C. Lin,*, Y.-J. Chen,* “Nanoprobe-Based Affinity Mass Spectrometry for Selected Protein Profiling in Human Plasma” Anal. Chem. 2005, 77, 5990-5997. (SCI, IF:5.874; 5 year-IF:5.902 ; ranking: 3/73)

2.P.-C. Lin, P.-H. Chou, S.-H. Chen, H.-K. Liao, K.-Y. Wang, Y.-J. Chen, C.-C. Lin,* “Ethylene Glycol-Protected Magnetic Nanoparticles for a Multiplexed Immunoassay in Human Plasma” Small, 2006, 2, 485-489. (SCI, IF: 7.333; 5 year-IF:8.057; ranking: 7/64)

3.P.-C. Lin, S.-H. Ueng, M.-C. Tseng, J.-L. Ko, K.-T. Huang, S.-C. Yu, A. K. Adak, Y.-J. Chen, C.-C. Lin,* “Site-Specific Protein Modification through Cui-Catalyzed 1,2,3-Triazole Formation and Its Implementation in Protein Microarray Fabrication“ Angew. Chem. Int. Ed. 2006, 45, 4286-4290. (SCI, IF: 12.730; 5 year-IF:12.05; ranking: 5/147)

4. P.-C. Lin, M.-C. Tseng, A.-K. Su, Y.-J. Chen*, C.-C. Lin,* “Functionalized Magnetic Nanoparticles for Small-Molecule Isolation, Identification, and Quantification“ Anal. Chem. 2007, 79, 3401-3408.  (SCI, IF: 5.874; 5 year-IF: 5.902; ranking: 3/73)

5.P.-C. Lin, S.-H. Ueng, S.-C. Yu, M.-D. Jan, A. K. Adak, C.-C. Yu, C.-C. Lin,* “Surface Modification of Magnetic Nanoparticle via Cu(I)-Catalyzed Alkyne-azide [2 + 3] Cycloaddition” Org. Lett. 2007, 9, 2131-2134. (SCI, IF:5.250; 5 year-IF: 4.962; ranking: 5/56)

6.T.-C. Chiu, L.-S. Huang, P.-C. Lin, Y.-C. Chen, Y.-J. Chen, C.–C. Lin, H.-T. Chang, “Nanomaterial Based Affinity Matrix-assisted Laser Desorption/Ionization Mass Spectrometry for Biomolecules and Pathogenic Bacteria.” Recent patents on   Nanotechnology, 2007, 1, 99- 111.

(SCI, IF: 0.949; 5 year-IF: 1.037; ranking: 129/225)

7.C.-C. Yu, P.-C. Lin, C.-C. Lin* “Site-specific CMP-sialic acid synthetase Immobilized Magnetic Nanoparticle in the synthesis of CMP-sialic acid” Chem. Commun. 2008, 1308-1310. (Co-first authors)  (SCI, IF: 5.787; 5 year-IF: 5.581; ranking: 17/147)

8. P.-H. Shih, J.-Y. Shiu, P.-C. Lin, C.-C. Lin, T. Veres, P. Chen, “On chip sorting of bacterial cells using sugar-encapsulated magnetic nanoparticles” J. Appl. Phys. 2008, 103, 07A316.  (SCI, IF: 2.064; 5 year-IF: 2.201; ranking: 34/118 )

9. K.-Y. Wang, S.-A. Chuang, P.-C. Lin, S.-H. Chen, L.-S. Huang, C.-C. Lin, and Y.-J. Chen* “Multiplexed Immunoassay: Quantitation and Profiling of Serum Biomarkers Using Magnetic Nanoprobes and MALDI-TOF MS“ Anal. Chem., 2008, 80, 6159-6167.

(SCI, IF: 5.874; 5 year-IF: 5.902; ranking: 3/73)

10. P.-C. Lin, H.-T. Wu, K.-Y. Wang, Y.-J. Chen, C.-C. Lin, “Development and Application of Functionalized Nanoparticles on Mass Spectrometry for the Analysis of Target Biomolecules” Instruments Today, 2008, 29, 68. (in Taiwan)

11. P.-C. Lin, S.-H. Chen, M.-L. Chen, A. Kumar Adak, Y.-J. Chen* and C.-C. Lin*, “Fabrication of Oriented Antibody-Conjugated Magnetic Nanoprobes and Their Immunoaffinity Application” Anal. Chem. 2009,81, 8774.

 (SCI, IF: 5.874; 5 year-IF: 5.902; ranking: 3/73)

12.P.-C. Lin, A. K. Adak, S.-H. Ueng, L.-D. Huang, K.-T.Huang, C.-C. Lin, “DAST-Mediated Regioselective Anomeric Group Migration in Saccharides”,  J. Org. Chem. 2009, 74, 4041-4048. (SCI, IF:4.002; 5 year-IF: 3.818; ranking: 8/56)

13.P.-C. Lin, D. Weinrich, H. Waldmann, „Protein Biochips: Oriented Surface Immobilization of Proteins“Marcromol. Chem. Phys. 2010, 211, 136-144. (SCI, IF: 2.437; 5 year-IF: 2.416; ranking: 19/79)

14. D. Weinrich, P.-C. Lin, P. Jonkheijm, H. Schröder, C. M. Niemeyer, K. Alexandrov, H. Waldmann. „Oriented Immobilization of Farnesylated Proteins by Thiol-Ene Reaction “Angew. Chem. Int. Ed. 2010, 49,1252-1257.  (SCI, IF: 12.730; 5 year-IF:12.05; ranking: 5/147)

15. M.-C. Tseng,R. Obena,Y.-W. Lu,P.-C. Lin,P.-Y. Lin,Y.-S. Yen,J.-T. Lin,L.-D. Huang,K.-L. Lu,L.-L. Lai,C.-C. Lin,Y.-J. Chen “Dihydrobenzoic Acid Modified Nanoparticle as a MALDI-TOF MS Matrix for Soft Ionization and Structure Determination of Small Molecules with Diverse Structures”J. Am. Soc. Mass Spectrom. 2010, 11, 1930. (SCI, IF: 3.83; 5 year-IF:3.625; ranking: 5/42)

16. W.-C. Chen, P.-C. Lin, C.-H. Chen, C.-T. Chen, Chem. Euro. J. 2010, 43, 12822.  (SCI, IF: 5.476; 5 year-IF:5.477; ranking: 18/147)

17.H.-T. Wu, C.-C. Hsu, C.-F. Tsai, P.-C. Lin, C.-C. Lin*and Y.-J. Chen,^”Nanoprobe-based Immobilized Metal Affinity Chromatography for Enhanced Enrichment of Multiply Phosphorylated Peptides” Proteomics 2011, 11, 2639. (SCI, IF:4.815; 5 year-IF:4.94; ranking: 13/71)

18. R. P. Obena, P.-C. Lin, Y.-W. Lu, I.-C. Li, F. Del Mundo, S. D. Arco, G.M. Nuesca, C.-C. Lin, Y.-J. Chen, “Iron oxide nanomatrix facilitating metal ionization in matrix-assisted laser desorption/ionization mass spectrometry.”Anal. Chem. 2011, 83, 9337. (SCI, IF: 5.874; 5 year-IF:5.902; ranking: 3/73)

19.Yi L, Chen YX, Lin PC, Schröder H, Niemeyer CM, Wu YW, Goody RS, Triola G, Waldmann H., “Direct immobilization of oxyamine-modified proteins from cell lysates” Chem. Commun. 2012, 48, 10829-10831. (SCI, IF: 5.787; 5 year-IF: 5.581; ranking: 17/147)

20. Po-Chiao Lin,^* Ching-Ching Yu, Huan-Ting Wu, Ying-Wei Lu, Chia-Li Han, An-Kai Su, Yu-Ju Chen,^* Chun-Cheng Lin,^* “A Chemically Functionalized Magnetic Nanoplatform for Rapid and Specific Biomolecular Recognition and Separation” Biomacromolecule 2013, 14, 160-168. (*corresponding author; ) (SCI, IF:5.479; ranking: 3/79)

21. Yung-Lin Yang, Basker Rajagopal, Chien-Fu Liang, Chun-Chi Chen, Hsiu-Ping Lai, Chih-Hung Chou, Yen-Pin Lee, Yen-Ling Yang, Jing-Wen Zeng, Chun-Lin Ou, Po-Chiao Lin,* “Chemoselective Synthesis of Aryl Carboxamido Sulfonic Acid Derivatives” Tetrahedron 2013, 69, 2640-2646. (*corresponding author; DOI: 10.1016/j.tet.2013.01.028) (SCI, IF: 3.025; ranking: 16/56)

22. Chun-Chi Chen, Yung-Lin Yang,Chun-Lin Ou, Chih-Hung Chou, Chih-Chuang Liaw, and Po-Chiao Lin,* “Direct Monitoring of Chemical Transformations by Combining Thin Layer Chromatography with Nanoparticle-assisted Laser Desorption/Ionization Mass Spectrometry” Analyst 2013,138, 1379-1385. (*corresponding author)  (SCI, IF:4.230; ranking: 8/73)

23. Yung-Lin Yang, Yen-Pin Lee, Yen-Ling Yang, Po-Chiao Lin* “Traceless Labeling of Glycoproteins and Its Application to the Study of Glycoprotein-protein Interact” ACS Chem. Biol. 2014, 9 ,390–397. (*corresponding author) (SCI, IF: 5.442; ranking: 48/290 in biochem & mol. bio)

24.Chun-Chi Chen, Basker Rajagopal, Xuan Yu Liu, Kuan Lin Chen, Yu-Chang Tyan, FuI Lin, Po-Chiao Lin * "A mild removal of Fmoc group using sodium azide" Amino Acids. 2014 ,46, 367-74 (SCI, IF: 3.914; ranking: 86/290 in biochem & mol. bio)

25. Basker Rajagopal , Ying-Yu Chen , Chun-Chi Chen , Xuan-Yu Liu , Huei-Ren Wang , and Po-Chiao Lin * "Cu(I)-Catalyzed Synthesis of Dihydropyrimidin-4-ones toward the Preparation of β- and β3-Amino Acid Analogues" J. Org. Chem., 2014, 79,1254–1264 (SCI, IF: 4.564; ranking: 10/57)

Patents:

1. 1.      Y.-J. Chen, P.-C. Lin, C.-C. Lin, S.-H. Chen, P.-H. Chou, H.-K. Liao (2007): Mass spectrometric analysis of ligand conjugated magnetic nanoparticles, U. S. Appl. Publ.  US20070054407

Book chapters:

1. L.-S. Huang, Y.-Y. Chien, S.-H. Chen, P.-C. Lin, K.-Y. Wang, P.-H. Chou, C.-C. Lin, and Y.-J. Chen,“Nanoprobe-based Affinity Mass  Spectrometry  for Cancer Marker Protein Profiling”in Nanomaterials for Cancer Diagnosis; Eds: Challa S. S. R. Wiley-VCH, 2007

2. P.-C. Lin,A. Kumar Adak, and C.-C. Lin*,“Fabrication and applications of glyconanomaterials.” in The Molecular Immunology of Complex Carbohydrates-3; Eds: Albert M. Wu, Kluwer Academia/Plenum Publishers, 2011

3.Wei-Ting Chien, Ching-Ching Yu, Chien-Fu Liang, Chien-Hui Lai, Po-Chiao Lin,* Chun-Cheng Lin,* Functionalized glyconanoparticles for the study of glycobiology” in Glyco-nanotechnology as a bridge to new medicines, ACS Symposium Series 1091, 2011, chapter 2, p15-36. 

 為了慰勞大家2013年一年的辛勞,歲末來一次墾丁行!!!

check in 中

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擺pose也只能趁現在了~

Double S girls

打到會變 笨!!

Ph. D     

實驗室合照

LPC GO GO !