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- W2064757557 abstract "The N-protected heptapeptide sulfoxide corresponding to positions 5 to 11 inclusive of substance P, Boc-Gln-Gln-Phe-Phe-Gly-Leu-Met(O)-NH2 (VII), was synthesized by the repetitive excess mixed anhydride (REMA) method (Scheme). Consecutive mixed anhydride coupling to N-deprotected VII of the dipeptides Boc-Lys(Z)-Pro-OH (VIII) and Z-Arg(NO2)-Pro-OH (X) yielded protected substance P sulfoxide, XI. From XI both Z groups and the NO2 group were removed with liquid hydrogen fluoride, yielding substance P sulfoxide. Substance P sulfoxide was conveniently reduced to substance P with the aid of iodide ions in strongly acid olution. Preliminary results are given on the scope of this method, i.e. peptides containing - besides methionine - tyrosine, where the method worked well, or tryptophan, where the method failed. REMA-synthesized substance P, after gel filtration, was found to be chemically pure and to possess the same biological activity as a substance P standard (Beckman), according to two tests (sialagogic assay and guinea pig ileum contraction)." @default.
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- W2064757557 date "1978-01-01" @default.
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- W2064757557 title "Synthesis of substance P via its sulfoxide by the repetitive excess mixed anhydride (REMA) method" @default.
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- W2064757557 doi "https://doi.org/10.1002/recl.19780970102" @default.
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