Stereoselective synthesis of 4-amino-3-hydroxy-2-methylpentanoic acids: stereochemistry of the amino acid occurring in the marine toxin janolusimide |
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| Institution: | 1. Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou 350108, China;2. National Engineering Research Center of Chemical Fertilizer Catalyst, College of Chemical Engineering, Fuzhou University, Fuzhou 350108, China;3. Max Planck Institute of Molecular Physiology, Department of Chemical Biology, Dortmund 44227, Germany |
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| Abstract: | Four diastereomers of 4-amino-3-hydroxy-2-methylpentanoic acid, an amino acid constituent of the hexapeptide portion of the antitumor antibiotic bleomycin A2, have been stereoselectively synthesized by crotylboration of N-Boc-l-alaninal. The synthesis allowed the assignment of the stereochemistry as 2R,3S,4S to the 4-amino-3-hydroxy-2-methylpentanoic acid occurring in the tripeptide marine toxin janolusimide. |
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