SOLID PHASE SYNTHESIS OF PORCINE LH-RELEASING HORMONE WITH HYDROGEN CHLORIDE IN FORMIC ACID AS THE DEBLOCKING REAGENT*
- 12 January 2009
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 11 (1) , 19-27
- https://doi.org/10.1111/j.1399-3011.1978.tb02816.x
Abstract
The decapeptide corresponding to the amino acid sequence of porcine luteinizing hormone-releasing hormone (LH-RH) which involves 1 mol of tryptophan was synthesized via solid phase synthesis with 2 different deblocking procedures which used HCl in formic acid and HCl in acetic acid containing 1% 2-mercaptoethanol. After some fundamental studies on the former reagent with respect to deblocking efficiency toward the Boc [tert-butyloxycarbonyl] group, 0.5 M HCl (a 10-fold molar excess with respect to the N-terminal Boc group) in formic acid was used in the present synthesis. The 2 synthetic products exhibited the same chemical and biological properties as an authentic LH-RH. HCl in formic acid has proved effective without a scavenger although loss of peptide from the resin occurred to a somewhat greater extent than that with HCl in acetic acid. A derivative of the synthetic LH-RH formylated at the indole N had a greatly diminished biological activity, indicating that the intact indole side chain is essential for the activity.Keywords
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