Appl Microbiol. 1975 Oct;30(4):650-6.

Enzymatic transformation of morphine by hydroxysteroid dehydrogenase from Pseudomonas testosteroni.

Abstract

Eznyme preparations from Pseudomonas testosteroni containing alpha- and beta- 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 carred out by the hydroxysteroid dehydrogenase. Hydroxylation at the 14-position did occur spontaneously (or enzymatically with a contaminating enzyme) ater oxidation at the 6-position.

PMID:: 172013; [PubMed - indexed for MEDLINE]
PMCID:: PMC187243

Free PMC Article

LinkOut - more resources

Full Text Sources

Molecular Biology Databases

Supplemental Content

Save items

Related citations in PubMed

Microbial degradation of the morphine alkaloids: identification of morphine as an intermediate in the metabolism of morphine by Pseudomonas putida M10. [Arch Microbiol. 1990]
Microbial degradation of the morphine alkaloids: identification of morphine as an intermediate in the metabolism of morphine by Pseudomonas putida M10.
Bruce NC, Wilmot CJ, Jordan KN, Trebilcock AE, Gray Stephens LD, Lowe CR. Arch Microbiol. 1990; 154(5):465-70.
Metabolism of dexamethasone in the human kidney: nicotinamide adenine dinucleotide-dependent 11beta-reduction. [J Clin Endocrinol Metab. 1997]
Metabolism of dexamethasone in the human kidney: nicotinamide adenine dinucleotide-dependent 11beta-reduction.
Diederich S, Hanke B, Oelkers W, Bähr V. J Clin Endocrinol Metab. 1997 May; 82(5):1598-602.
On the 3alpha-hydroxysteroid dehydrogenase from Pseudomonas testosteroni. The effect of denaturing agents. [Int J Pept Protein Res. 1975]
On the 3alpha-hydroxysteroid dehydrogenase from Pseudomonas testosteroni. The effect of denaturing agents.
Skålhegg BA. Int J Pept Protein Res. 1975; 7(4):335-9.
Review Isozymes of 11 beta-hydroxysteroid dehydrogenase: which enzyme endows mineralocorticoid specificity? [Steroids. 1994]
Review Isozymes of 11 beta-hydroxysteroid dehydrogenase: which enzyme endows mineralocorticoid specificity?
Krozowski ZS, Provencher PH, Smith RE, Obeyesekere VR, Mercer WR, Albiston AL. Steroids. 1994 Feb; 59(2):116-20.
Review The pharmacogenetics of codeine hypoalgesia. [Pharmacogenetics. 1995]
Review The pharmacogenetics of codeine hypoalgesia.
Sindrup SH, Brøsen K. Pharmacogenetics. 1995 Dec; 5(6):335-46.

See reviews... See all...

Cited by 4 PubMed Central articles

Transformation of 2,2'-bimorphine to the novel compounds 10-alpha-S-monohydroxy-2,2'-bimorphine and 10,10'-alpha,alpha'-S,S'-dihydroxy-2,2'-bimorphine by Cylindrocarpon didymum. [Appl Environ Microbiol. 2001]
Transformation of 2,2'-bimorphine to the novel compounds 10-alpha-S-monohydroxy-2,2'-bimorphine and 10,10'-alpha,alpha'-S,S'-dihydroxy-2,2'-bimorphine by Cylindrocarpon didymum.
Stabler PJ, Holt PJ, Bruce NC. Appl Environ Microbiol. 2001 Aug; 67(8):3716-9.
Biological synthesis of the analgesic hydromorphone, an intermediate in the metabolism of morphine, by Pseudomonas putida M10. [Appl Environ Microbiol. 1993]
Biological synthesis of the analgesic hydromorphone, an intermediate in the metabolism of morphine, by Pseudomonas putida M10.
Hailes AM, Bruce NC. Appl Environ Microbiol. 1993 Jul; 59(7):2166-70.
Identification of transformation products arising from bacterial oxidation of codeine by Streptomyces griseus. [Appl Environ Microbiol. 1985]
Identification of transformation products arising from bacterial oxidation of codeine by Streptomyces griseus.
Kunz DA, Reddy GS, Vatvars A. Appl Environ Microbiol. 1985 Oct; 50(4):831-6.

See all...

Related information

Related Citations
Calculated set of PubMed citations closely related to the selected article(s) retrieved using a word weight algorithm. Related articles are displayed in ranked order from most to least relevant, with the “linked from” citation displayed first.
Compound
PubChem chemical compound records that cite the current articles. These references are taken from those provided on submitted PubChem chemical substance records. Multiple substance records may contribute to the PubChem compound record.
Compound (MeSH Keyword)
PubChem chemical compound records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.
References for this PMC Article
Citation referenced in PubMed article. Only valid for PubMed citations that are also in PMC.
Substance
PubChem chemical substance records that cite the current articles. These references are taken from those provided on submitted PubChem chemical substance records.
Substance (MeSH Keyword)
PubChem chemical substance (submitted) records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.
Free in PMC
Free full text articles in PMC
Cited in PMC
Full-text articles in the PubMed Central Database that cite the current articles.

Recent activity

Clear Turn Off Turn On

Enzymatic transformation of morphine by hydroxysteroid dehydrogenase from Pseudo...
Enzymatic transformation of morphine by hydroxysteroid dehydrogenase from Pseudomonas testosteroni.
Appl Microbiol. 1975 Oct ;30(4):650-6.

PubMed
Arthroscopic lavage of osteoarthritic knees.
Arthroscopic lavage of osteoarthritic knees.
J Bone Joint Surg Br. 1991 Nov ;73(6):922-6.

PubMed
Anticancer potential of silymarin: from bench to bed side.
Anticancer potential of silymarin: from bench to bed side.
Anticancer Res. 2006 Nov-Dec ;26(6B):4457-98.

PubMed
Delayed thrombin generation is not associated with fibrinopeptide formation duri...
Delayed thrombin generation is not associated with fibrinopeptide formation during prolonged cardiopulmonary bypass with hirudin anticoagulation.
Perfusion. 2006 Dec ;21(5):259-62.

PubMed
Phase II trial of dose-dense doxorubicin plus gemcitabine followed by paclitaxel...
Phase II trial of dose-dense doxorubicin plus gemcitabine followed by paclitaxel plus carboplatin in patients with advanced urothelial carcinoma and impaired renal function.
Cancer. 2007 Feb 1 ;109(3):549-55.

PubMed

Your browsing activity is empty.

Activity recording is turned off.

Turn recording back on

PubMed

Result Filters

Display Settings:

Send to:

Enzymatic transformation of morphine by hydroxysteroid dehydrogenase from Pseudomonas testosteroni.

Abstract

MeSH Terms, Substances

MeSH Terms

Substances

LinkOut - more resources

Full Text Sources

Molecular Biology Databases

Supplemental Content

Save items

Related citations in PubMed

Cited by 4 PubMed Central articles

Related information

Recent activity

Simple NCBI Directory

Getting Started

Resources

Popular

Featured

NCBI Information