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Synthesis of tripeptide hydrolysate from papuamide A: determination of absolute stereostructure of β-methoxytyrosine
Authors:Kazuishi Makino
Institution:Graduate School of Pharmaceutical Sciences, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan
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.
Keywords:Papuamide A  β-Methoxytyrosine  Absolute stereochemistry  Relative stereochemistry
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