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Synthesis 2007(23): 3666-3672
DOI: 10.1055/s-2007-990848
DOI: 10.1055/s-2007-990848
PAPER
© Georg Thieme Verlag Stuttgart · New York
Stereoselective Synthesis of β-Methoxytyrosine Derivatives for Identification of the Absolute Configuration of Callipeltin E
Further Information
Publication History
Received
1 August 2007
Publication Date:
29 October 2007 (online)
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Abstract
Asymmetric syntheses of all diastereoisomers of β-methoxytyrosine, an unusual amino acid contained in callipeltin A, were accomplished starting from a cinnamyl ester derivative. The stereochemistry of β-methoxytyrosine in callipeltin E was estimated to be 2R,3R by 1H and 13C NMR analyses of four diastereoisomeric tripeptides, each containing a β-methoxytyrosine isomer. These results obtained from the synthetic peptide derivatives were identical to D’Auria’s results obtained by a degradative procedure.
Key words
callipeltin - cyclodepsipeptide - β-methoxytyrosine - marine sponge - unusual amino acid - anti-HIV activity