PMID:18071270
| Citation |
Nakaya, M, Oguri, H, Takahashi, K, Fukushi, E, Watanabe, K and Oikawa, H (2007) Relative and absolute configuration of antitumor agent SW-163D. Biosci. Biotechnol. Biochem. 71:2969-76 |
|---|---|
| Abstract |
Our interest on engineering non-ribosomal synthetase responsible for SW-163 biosynthesis prompted us to determine the relative and absolute configuration of antitumor cyclic depsipeptide SW-163s. We first isolated and identified SW-163 homologs D, F and G as known compounds UK-63598, UK-65662 and UK-63052, respectively. Both enantiomers of the unusual constitutive amino acid, N-methylnorcoromic acid, were synthesized in chiral forms starting from (R)- and (S)-1,2-propanediol. The hydrolyzate of SW-163D, a major constituent of this family, was converted with Marfey's reagent, 1-fluoro-2,4-dinitrophenyl-5-L-alanine-amide (L-FDAA), and the resulting mixture of amino acid derivatives was subjected to an LC/MS analysis. Compared with authentic samples, the analytical data unambiguously show that SW-163D consisted of L-Ala, D-Ser and (1S, 2S)-N-methylnorcoronamic acid. The remaining stereochemistry of the N-methylcysteine moieties was determined from NOE data. |
| Links | |
| Keywords |
Alkaloids/chemistry; Amino Acids/chemistry; Antineoplastic Agents/chemical synthesis; Antineoplastic Agents/chemistry; Chromatography, High Pressure Liquid; Cyclopropanes/chemistry; Depsipeptides/chemical synthesis; Depsipeptides/chemistry; Echinomycin/analogs & derivatives; Echinomycin/chemical synthesis; Echinomycin/chemistry; Leucine/analogs & derivatives; Leucine/chemistry; Mass Spectrometry; Molecular Conformation; Nitro Compounds/chemistry; Propylene Glycol/chemistry; Quinolizines/chemistry; Stereoisomerism |
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