Journal of Cancer Research and Experimental Oncology
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Article Number - AF3E1A241025


Vol.5(1), pp. 8-19 , November 2013
DOI: 10.5897/JCREO2013.0102
ISSN: 2141-2243



Full Length Research Paper

Solid-phase total synthesis of cyclic pentapeptide Longicalycinin A, by using 2-chlorotrityl chloride resin



Waqar Ahmad
  • Waqar Ahmad
  • State Key Laboratory of Chemical Resource Engineering, Institute of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. China.
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Farzana Shaheen
  • Farzana Shaheen
  • International Center for Chemical and Biological Sciences, University of Karachi, 75270, Pakistan.
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Yunshan Zhou
  • Yunshan Zhou
  • State Key Laboratory of Chemical Resource Engineering, Institute of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. China.
  • Google Scholar
Lijuan Zhang
  • Lijuan Zhang
  • State Key Laboratory of Chemical Resource Engineering, Institute of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. China.
  • Google Scholar







 Accepted: 03 October 2013  Published: 30 November 2013

Copyright © 2013 Author(s) retain the copyright of this article.
This article is published under the terms of the Creative Commons Attribution License 4.0


Naturally isolated cyclic pentapeptide Longicalycinin A, which showed cytotoxicity to Hep G2 cancer cell line with an IC50 value 13.52 μg/mL, has been successfully synthesized by solid-phase methodology with Fmoc/t-Bu protecting schemes via solution-phase macrocyclization. 2-chlorotrityl chloride resin was used as solid support. Solution phase macrocyclization of linear pentapeptide precursor was carried out by two different routes with mild and severe acidic conditions correspondingly and found that percentage yield of Longicalycinin A under mild acidic condition (33%) was better than severe acidic conditions (13.7%). In addition, the cytotoxicity against Dalton’s lymphoma ascites (DLA) and Ehrlich’s ascites carcinoma (EAC) cell lines with CTC50 values were found to be 2.62 and 6.17 µM respectively.

 

Key words: Longicalycinin A, solid phase synthesis, 2-chlorotrityl chloride, solution-phase macrocyclization, cytotoxicity.

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APA (2013). Solid-phase total synthesis of cyclic pentapeptide Longicalycinin A, by using 2-chlorotrityl chloride resin. Journal of Cancer Research and Experimental Oncology, 5(1), 8-19.
Chicago Waqar Ahmad, Farzana Shaheen, Yunshan Zhou and Lijuan Zhang. "Solid-phase total synthesis of cyclic pentapeptide Longicalycinin A, by using 2-chlorotrityl chloride resin." Journal of Cancer Research and Experimental Oncology 5, no. 1 (2013): 8-19.
MLA Waqar Ahmad, et al. "Solid-phase total synthesis of cyclic pentapeptide Longicalycinin A, by using 2-chlorotrityl chloride resin." Journal of Cancer Research and Experimental Oncology 5.1 (2013): 8-19.
   
DOI 10.5897/JCREO2013.0102
URL http://academicjournals.org/journal/JCREO/article-abstract/AF3E1A241025

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