Synthesis of tripeptide hydrolysate from papuamide A: determination of absolute stereostructure of β-methoxytyrosine |
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Authors: | Kazuishi Makino |
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Institution: | Graduate School of Pharmaceutical Sciences, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan |
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Abstract: | Four diastereomers, (2R,3R), (2S,3S), (2S,3R) and (2R,3S) at β-methoxytyrosine (β-OMeTyr), of the tripeptide hydrolysate, H-(S)-N-MeThr-β-OMeTyr-(S)-Hpr-OH, from papuamide A have been synthesized. Comparison of the 1H NMR data of the natural hydrolysate with the four synthetic diastereomers unambiguously establishes the relative and absolute stereochemistry of the methoxytyrosine as 2R,3R. |
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Keywords: | Papuamide A β-Methoxytyrosine Absolute stereochemistry Relative stereochemistry |
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