International Journal of Scientific & Technology Research

Home About Us Scope Editorial Board Blog/Latest News Contact Us
10th percentile
Powered by  Scopus
Scopus coverage:
Nov 2018 to May 2020


IJSTR >> Volume 5 - Issue 5, May 2016 Edition

International Journal of Scientific & Technology Research  
International Journal of Scientific & Technology Research

Website: http://www.ijstr.org

ISSN 2277-8616

Synthesis Of Three Analogues Of Trypsin-Modulating Oostatic Factor (TMOF) And Screening Of Their Insecticidal Properties Towards Cabbage Cluster Caterpillar

[Full Text]



Rani Maharani, Ari Hardianto, Safri Ishmayana, Eka Fitri Yanti, Devia Irma Melati, Daniel Sihotang, Lindung Tri Puspasari, Danar Dono



Trypsin-modulating oostatic factor, TMOF, Aedes aegypty, Crocidolomia pavonana, solid-phase peptide synthesis, 2-chlorotrityl chloride resin, DIC/Oxyma.



Three analogues of TMOF, [PP (H-Pro-Pro-OH), PPPPPP (H-Pro-Pro-Pro-Pro-Pro-Pro-OH), and APPPPPP (H-Pro-Pro-Pro-Pro-Pro-Pro-OH)], were successfully synthesised and screened for their insecticidal properties against cabbage cluster caterpillar (Crocidolomia pavonana). All compounds were prepared through Fmoc-based solid-phase peptide synthesis (SPPS) method. The synthesis employed chlorotrityl resin as solid support. A combination of N,N-diisopropylcarbodiimide (DIC) and ethyl 2-cyano-2-(hydroxyimino)acetate (oxyma) was chosen as coupling reagent in the synthesis. The peptide was cleaved by using TFA cocktail. All peptide crudes were purified by using reversed-phase flash chromatography with octadecyl silane (ODS) as stationary phase. All purified peptides were characterized by using TOF-ESMS and their purity was analysed using thin layer chromatography and analytical RP-HPLC. The synthesised TMOF analogues, together with TMOF, were biologically tested towards the (C. pavonana) at 1000 ppm. The results indicated that TMOF and the analogues were less effective for the cabbage cluster caterpillar, compared to previously reported activity of TMOF towards Aedes aegypty.



[1] D. Borovsky, D. Carlson, P. Griffin, J. Shabanowitz, D. Hunt, "Mosquito oostatic factor: a novel decapeptide modulating trypsin-like enzyme biosynthesis in the midgut", The FASEB Journal, vol.4, pp. 3015-20, 1990.

[2] D. Borovsky, "Trypsin-modulating oostatic factor: a potential new larvicide for mosquito control", Journal of experimental biology, vol. 206, pp. 3869-75, 2003.

[3] D. Borovsky, R. Nauen, "Biological and biochemical effects of organo-synthetic analogues of Trypsin Modulating Oostatic Factor (TMOF) on Aedes aegypti, Heliothis virescens and Plutella xylostella", PESTYCYDY-WARSZAWA, vol. 3, p. 17, 2007.

[4] R. Maharani, E.F. Yanti, M.D.I Melati, D. Sihotang, "Synthesis of Trypsin-modulating Oostatic Factor (TMOF) and its Analogues by Solid-phase Peptide Synthesis Using DIC/Oxyma as Coupling Reagent", Procedia Chemistry, vol. 17, pp. 125-31, 2015.

[5] K. Barlos, O. Chatzi, D. Gatos, G. Stavropoulos, "2-Chlorotrityl chloride resin. Studies on anchoring of Fmoc-amino acids and peptide cleavage", Int J Pept Protein Res, vol. 37, pp. 513, 1991.

[6] S.Y. Han, Y.A. Kim, "Recent development of peptide coupling reagents in organic synthesis", Tetrahedron, vol. 60, pp. 2447-67, 2004.

[7] W.C. Chan and P.D. White, "Fmoc Solid Phase Peptide Synthesis: A practical approach", New York: Oxford University Press; 2000.

[8] R. Subirós‐Funosas, R. Prohens, R. Barbas, A. El‐Faham, F. Albericio, "Oxyma: An Efficient Additive for Peptide Synthesis to Replace the Benzotriazole‐Based HOBt and HOAt with a Lower Risk of Explosion [1]", Chemistry-a European Journal, vol. 15, pp. 9394-403, 2009.

[9] T. Vojkovsky, "Detection of secondary amines on solid phase" Pept Res, vol. 8, p. 236, 1995.