Skip to main content
PMC home page
Applied Microbiology logoLink to Applied Microbiology
. 1975 Oct;30(4):650–656. doi: 10.1128/am.30.4.650-656.1975

Enzymatic Transformation of Morphine by Hydroxysteroid Dehydrogenase from Pseudomonas testosteroni

Paloma Liras 1,1, Stephen S Kasparian 1,2, Wayne W Umbreit 1
PMCID: PMC187243  PMID: 172013

Abstract

Enzyme preparations from Pseudomonas testosteroni containing α- and β-hydroxysteroid dehydrogenases catalyzed the oxidation of morphine and codeine by nicotinamide adenine dinucleotide. Morphine was converted in relatively low yield into 14-hydroxymorphinone probably via morphinone as an intermediate. Codeine was converted to codeinone and 14-hydroxycodeinone. Only the conversions at the 6-position were carried out by the hydroxysteroid dehydrogenase. Hydroxylation at the 14-position did occur spontaneously (or enzymatically with a contaminating enzyme) after oxidation at the 6-position.

Full text

PDF
650

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. DALZIEL K. The purification of nicotinamide adenine dinucleotide and kinetic effects of nucleotide impurities. J Biol Chem. 1963 Apr;238:1538–1543. [PubMed] [Google Scholar]
  2. DELIN S., SQUIRE P. G., PORATH J. PURIFICATION OF STEROID-INDUCED ENZYMES FROM PSEUDOMONAS TESTOSTERONI. Biochim Biophys Acta. 1964 Sep 18;89:398–408. doi: 10.1016/0926-6569(64)90066-5. [DOI] [PubMed] [Google Scholar]
  3. Liras P. Thin-layer and gas chromatographic parameters of morphine and codeine derivatives. J Chromatogr. 1975 Mar 19;106(1):238–240. doi: 10.1016/s0021-9673(01)81073-6. [DOI] [PubMed] [Google Scholar]
  4. MARCUS P. I., TALALAY P. Induction and purification of alpha- and beta-hydroxysteroid dehydrogenases. J Biol Chem. 1956 Feb;218(2):661–674. [PubMed] [Google Scholar]
  5. RACKER E. Crystalline alcohol dehydrogenase from baker's yeast. J Biol Chem. 1950 May;184(1):313–319. [PubMed] [Google Scholar]
  6. Roe C. R., Kaplan N. O. Purification and substrate specificities of bacterial hydroxysteroid dehydrogenases. Biochemistry. 1969 Dec;8(12):5093–5103. doi: 10.1021/bi00840a063. [DOI] [PubMed] [Google Scholar]
  7. SQIRE P. G., DELIN S., PORATH J. PHYSICAL AND CHEMICAL CHARACTERIZATION OF HYDROXYSTEROID DEHYDROGENASES FROM PSEUDOMONAS TESTOSTERONI. Biochim Biophys Acta. 1964 Sep 18;89:409–421. doi: 10.1016/0926-6569(64)90067-7. [DOI] [PubMed] [Google Scholar]
  8. TALALAY P., DOBSON M. M. Purification and properties of a beta-hydroxysteroid dehydrogenase. J Biol Chem. 1953 Dec;205(2):823–837. [PubMed] [Google Scholar]
  9. TALALAY P., MARCUS P. I. Enzymatic formation of 3 alpha-hydroxysteroids. Nature. 1954 Jun 19;173(4416):1189–1190. doi: 10.1038/1731189a0. [DOI] [PubMed] [Google Scholar]
  10. TALALAY P., MARCUS P. I. Specificity, kinetics, and inhibition of alpha- and beta-hydroxysteroid dehydrogenases. J Biol Chem. 1956 Feb;218(2):675–691. [PubMed] [Google Scholar]
  11. WINER A. D. CRYSTALLIZATION OF NICOTINAMIDE ADENINE DINUCLEOTIDE. J Biol Chem. 1964 Oct;239:PC3598+–PC3598+. [PubMed] [Google Scholar]

Articles from Applied Microbiology are provided here courtesy of American Society for Microbiology (ASM)

RESOURCES