Author Topic: Advances in morphine synthesis and biosynthesis  (Read 26182 times)

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Advances in morphine synthesis and biosynthesis
« on: February 17, 2004, 05:26:00 AM »
Current Organic Chemistry 4, 343-62 (2000)

Abstract: This review covers recent developments in the area of morphine synthesis and biosynthesis.  Literature is reviewed since the publication of the last major review.   The first part of this chapter discusses recent advancements in biosynthesis of morphine alkaloids.  Total syntheses published since 1996 are reviewed next and the third section discusses all published approaches to morphine skeleton.  At the end of the chapter, an additional reference list is provided for synthesis of medicinally important derivatives, improvements in alkoloid interconversion, as well as a list of all dissertations dealing with morphine synthesis.

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Biotransformation of Morphine to Hydromorphone
« Reply #1 on: September 09, 2004, 04:44:00 PM »
Transformations of Morphine Alkaloids by Pseudomonas putida M10
Marianne T. Long, Anne M. Hailes, Gordon W. Kirby, and Neil C. Bruce
Applied and Environmental Microbiology, 61(10), 3645–3649 (1995)

The oxidation of morphine by washed-cell incubations of Pseudomonas putida M10 gave rise to a large number of transformation products including hydromorphone (dihydromorphinone), 14?-hydroxymorphine, 14?-hydroxymorphinone, and dihydromorphine. Similarly, in incubations with oxymorphone (14?-hydroxydihydromorphinone) as substrate, the major transformation product was identified as oxymorphol (14?-hydroxydihydromorphine). The identities of all these biological products were confirmed by mass spectrometry and 1H nuclear magnetic resonance spectroscopy. This is the first report describing structural evidence for the biological synthesis of 14?-hydroxymorphine and 14?-hydroxymorphinone. These products have applications as intermediates in the synthesis of semisynthetic opiate drugs.