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Synthesis of porcine motilin via its sulfoxides
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AbstractThe protected segments corresponding to sequences 1‐8 and 9‐22 proposed for porcine motilin were synthesized mainly by the repetitive excess mixed anhydride (REMA) method. Mixed anhydride coupling of the segments gave protected motilin sulfoxide (Scheme). Deprotection with liquid hydrogen fluoride yielded the crude motilin sulfoxides which, after purification by HPLC on a semi‐preparative scale, were quantitatively reduced by iodide in aqueous trifluoroacetic acid.According to Dr. Zen Itoh, Japan, the minimum dose of our REMA‐synthesized motilin required to induce interdigestive migrating contractions (IMC) in dogs was 0.03 μg/kg.h, which indicates a potency of about ten times the standard synthetic preparation used in the assay. In a comparison with natural porcine motilin by Dr. Pierre Poitras, U.S.A., REMA‐motilin showed at least 100% immunological cross‐reactivity.
Title: Synthesis of porcine motilin via its sulfoxides
Description:
AbstractThe protected segments corresponding to sequences 1‐8 and 9‐22 proposed for porcine motilin were synthesized mainly by the repetitive excess mixed anhydride (REMA) method.
Mixed anhydride coupling of the segments gave protected motilin sulfoxide (Scheme).
Deprotection with liquid hydrogen fluoride yielded the crude motilin sulfoxides which, after purification by HPLC on a semi‐preparative scale, were quantitatively reduced by iodide in aqueous trifluoroacetic acid.
According to Dr.
Zen Itoh, Japan, the minimum dose of our REMA‐synthesized motilin required to induce interdigestive migrating contractions (IMC) in dogs was 0.
03 μg/kg.
h, which indicates a potency of about ten times the standard synthetic preparation used in the assay.
In a comparison with natural porcine motilin by Dr.
Pierre Poitras, U.
S.
A.
, REMA‐motilin showed at least 100% immunological cross‐reactivity.
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