PRODUCTION OF HELODERMIN AND USE THEREOF

摘要

PURPOSE:To industrially obtain helodermin in high purity and yield by synthesizing a protected helodermin that is a new intermediate in which all the side-chain functional groups of constituent amino acids are protected and then removing the protecting groups. CONSTITUTION:An undecapeptide expressed by formula I (Boc is tert- butyloxycarbonyl; Bzl is benzyl; OcHex is cyclohexyl ester; Br-Z is 2- bromobenzyloxycarbonyl; X is tosyl or H) is condensed with a tetracosapeptide amide expressed by formula II (Cl-Z is 2-chlorobenzyloxycarbonyl; X2 is tosyl or mesitylene-2-sulfonyl) to provide a pentatriacosapeptide amide expressed by formula III. Protecting groups of the resultant pentatriacosapeptide amide are then removed with a strong acid (e.g. hydrogen fluoride or trifluoromethanesulfonic acid) to afford helodermin expressed by formula IV. The helodermin obtained by the aforementioned method is capable of acting not only on bloodstream but also specifically on musculus trachealis and used as a remedy for asthma.