Synthesis of Chlorotoxin by Native Chemical Ligation

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2018-04-01

Author

KARACA, Ulvi
Özçubukçu, Salih

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Chlorotoxin (CLTX) is a neurotoxin found in the venom of the Israeli scorpion, Leirius quinquestriatus. It contains 36-amino acids with four disulfide bonds and inhibits low-conductance chloride channels. CLTX also binds to matrix metalloproteinase-2 (MMP-2) selectively. The synthesis of chlorotoxin using solid phase peptide synthesis (SPPS) is very difficult and has a very low yield (<1%) due to high number of amino acid sequence. In this work, to improve the efficiency of the synthesis, native chemical ligation was applied. In this strategy, chlorotoxin sequence was split into two parts having 15 and 21 amino acids. 21-mer peptide was synthesized in its native form based on 9-fluorenylmethyloxycarbonyl (Fmoc) chemistry. 15-mer peptide was synthesized having o-aminoanilide linker on C-terminal. These parts were coupled by native chemical ligation to produce chlorotoxin.

Subject Keywords

Chlorotoxin, Solid phase peptide synthesis

URI

https://hdl.handle.net/11511/49235

Journal

Journal of the Turkish Chemical Society, Section A: Chemistry

DOI

https://doi.org/10.18596/jotcsa.408517

Collections

Department of Chemistry, Article

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Citation Formats

U. KARACA and S. Özçubukçu, “Synthesis of Chlorotoxin by Native Chemical Ligation,” Journal of the Turkish Chemical Society, Section A: Chemistry, pp. 719–726, 2018, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/49235.