Solid-phase syntheses of Glu20Ala20Phe and Ala20Glu20Phe by the step-by-step coupling of dipeptide and tetrapeptide.

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概要

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• Glu<SUB>20</SUB>Ala<SUB>20</SUB>Phe, (I), and Ala<SUB>20</SUB>Glu<SUB>20</SUB>Phe, (II), were synthesized by the step-by-step coupling of <I>N</I><SUP>α</SUP>-<I>t</I>-butoxycarbonyl (BOC-) derivatives of Ala–Ala and (γ-benzyl–Glu)<SUB>4</SUB> to phenylalanyl-1% crosslinked polystyrene resin using dicyclohexylcarbodiimide. The products were cleaved from the resin with hydrogen bromide in acetic acid and purified by gel filtration, followed by DEAE-cellulose chromatography, with yields of approximately 10% for both of the hentetracontapeptides. The optical purities of the glutamic acid and alanine incorporated in the pep tides, I and II, were estimated as 1 and 5% respectively from the analysis of the diastereomeric mixture of dipeptides derived from the reaction between the total acid hydrolyzate of I or II with the <I>N</I>-hydroxysucinimidyl ester of BOC–L-Leu.

• 公益社団法人 日本化学会の論文

著者

• Takahashi Sho

  Institute For Chemical Research Kyoto University

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• Solid-phase syntheses of Glu20Ala20Phe and Ala20Glu20Phe by the step-by-step coupling of dipeptide and tetrapeptide.

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