Vanoxonin, a new inhibitor of thymidylate synthetase. II. Structure determination and total synthesis.
- 1 January 1985
- journal article
- research article
- Published by Japan Antibiotics Research Association in The Journal of Antibiotics
- Vol. 38 (1) , 31-38
- https://doi.org/10.7164/antibiotics.38.31
Abstract
Acid hydrolysis of vanoxonin yielded 1 mol each of 2,3-dihydroxybenzoic acid, L-threonine, L-N.omega.-hydroxyornithine. Presence of acetyl group in vanoxonin was suggested by the 1H NMR. Periodate oxidation of vanoxonin liberated 1 mol of acetic acid, suggesting that the acetyl group bound to the .omega.-N of N.omega.-hydroxyornithine. The sequence of 3 components was determined to be L-N-(2,3-dihydroxybenzoyl)threonyl-L-(N.omega.-acetyl-N.omega.-hydroxy)ornithine by mass spectrometric analysis. This structure was confirmed by the total synthesis of vanoxonin.This publication has 1 reference indexed in Scilit:
- Microbial iron chelators: total synthesis of aerobactin and its constituent amino acid, N6-acetyl-N6-hydroxylysineJournal of the American Chemical Society, 1982