Investigations of the biosynthesis of novobiocin
- 1 December 1972
- journal article
- Published by Oxford University Press (OUP) in Journal of Pharmacy and Pharmacology
- Vol. 24 (12) , 972-978
- https://doi.org/10.1111/j.2042-7158.1972.tb08929.x
Abstract
The biosynthesis of novobiocin was investigated using isotopically labelled compounds. The amino-group of the coumarin unit was found to be derived from tyrosine, other typical 7-oxycoumarin precursors were not incorporated into the coumarin unit of novobiocin, 4′-hydroxyphenylpyruvate was a better precursor of the substituted benzoic acid unit than was 4′-hydroxycinnamic acid. A biosynthetic route to this unit of novobiocin is suggested. Synthetic pathways for 2′,4′-dihydroxyphenylalanine-1-14C and 4-hydroxybenzaldehyde-U-14C are reported for the first time.Keywords
This publication has 13 references indexed in Scilit:
- Biosynthesis of the aglycone of chartreusin in Streptomyces sp. X-465Phytochemistry, 1971
- Degradation of phenylalanine and tyrosine by Sporobolomyces roseusBiochemical Journal, 1968
- Measurement of Low Energy Beta-Emitters in Aqueous Solution by Liquid Scintillation Counting of Emulsions.Analytical Chemistry, 1965
- The formation of 7-oxygenated coumarins in hydrangea and lavenderPhytochemistry, 1965
- Experiments related to the biosynthesis of novobiocin and other coumarinsTetrahedron, 1963
- The biosynthesis of noviose, a branched-chain monosaccharideBiochimica et Biophysica Acta, 1962
- Formation of m- and p-coumaric acids by enzymatic deamination of the corresponding isomers of tyrosinePhytochemistry, 1961
- Further examples of biological c-methylation: novobiocin and actinomycinTetrahedron Letters, 1960
- The Structure of Novobiocin1,2Journal of the American Chemical Society, 1957
- 664. Formation of tyrosine melanin. Part III. The use of carboxyl-labelled tyrosine and dihydroxyphenylalanine in melanin formationJournal of the Chemical Society, 1952