恶臭假单胞菌M10对吗啡生物碱的转化
Transformations of morphine alkaloids by Pseudomonas putida M10.
作者信息
Long M T, Hailes A M, Kirby G W, Bruce N C
机构信息
Institute of Biotechnology, University of Cambridge, United Kingdom.
出版信息
Appl Environ Microbiol. 1995 Oct;61(10):3645-9. doi: 10.1128/aem.61.10.3645-3649.1995.
Abstract
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 beta-hydroxymorphine, 14 beta-hydroxymorphinone, and dihydromorphine. Similarly, in incubations with oxymorphone (14 beta-hydroxydihydromorphinone) as substrate, the major transformation product was identified as oxymorphol (14 beta-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 beta-hydroxymorphine and 14 beta-hydroxymorphinone. These products have applications as intermediates in the synthesis of semisynthetic opiate drugs.
摘要
恶臭假单胞菌M10的洗细胞培养物对吗啡的氧化产生了大量转化产物，包括氢吗啡酮（二氢吗啡酮）、14β-羟基吗啡、14β-羟基吗啡酮和二氢吗啡。同样，以羟吗啡酮（14β-羟基二氢吗啡酮）为底物进行培养时，主要转化产物被鉴定为羟吗啡醇（14β-羟基二氢吗啡）。所有这些生物产物的身份均通过质谱和1H核磁共振光谱得到证实。这是第一份描述14β-羟基吗啡和14β-羟基吗啡酮生物合成结构证据的报告。这些产物可作为半合成阿片类药物合成的中间体。
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