柱孢双孢霉将吗啡氧化为2,2'-二吗啡。
Oxidation of morphine to 2,2'-bimorphine by cylindrocarpon didymum.
作者信息
Stabler PJ, Bruce NC
机构信息
Institute of Biotechnology, University of Cambridge, Cambridge CB2 1QT, United Kingdom.
出版信息
Appl Environ Microbiol. 1998 Oct;64(10):4106-8. doi: 10.1128/AEM.64.10.4106-4108.1998.
Abstract
The oxidation of morphine by whole-cell suspensions and cell extracts of Cylindrocarpon didymum gave rise to the formation of 2, 2'-bimorphine. The identity of 2,2'-bimorphine was confirmed by mass spectrometry and 1H nuclear magnetic resonance spectroscopy. C. didymum also displayed activity with the morphine analogs hydromorphone, 6-acetylmorphine, and dihydromorphine, but not codeine or diamorphine, suggesting that a phenolic group at C-3 is essential for activity.
摘要
双隔孢柱孢菌的全细胞悬浮液和细胞提取物对吗啡的氧化作用导致了2,2'-双吗啡的形成。通过质谱和1H核磁共振光谱证实了2,2'-双吗啡的结构。双隔孢柱孢菌对吗啡类似物氢吗啡酮、6-乙酰吗啡和二氢吗啡也有氧化活性，但对可待因或二乙酰吗啡没有作用，这表明C-3位的酚羟基对于该氧化活性至关重要。
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本文引用的文献
1
The yields of Streptococcus faecalis grown in continuous culture.在连续培养中生长的粪肠球菌的产量。
J Gen Microbiol. 1960 Jun;22:726-39. doi: 10.1099/00221287-22-3-726.
2
FLUOROMETRIC IDENTIFICATION OF SUB-MICROGRAM AMOUNTS OF MORPHINE AND RELATED COMPOUNDS ON THIN-LAYER CHROMATOGRAPHS.薄层色谱上亚微克量吗啡及相关化合物的荧光鉴定
J Chromatogr. 1964 Dec;16:558-9. doi: 10.1016/s0021-9673(01)82532-2.
3
Mechanisms of steroid oxidation by microorganisms. XI. Enzymatic cleavage of the pregnane side chain.微生物对甾体氧化的机制。XI. 孕烷侧链的酶促裂解
J Biol Chem. 1966 Aug 10;241(15):3615-23.
4
Ion-pair high-performance liquid chromatographic determination of morphine and pseudomorphine in injections.
J Pharm Biomed Anal. 1992 Jul;10(7):507-14. doi: 10.1016/0731-7085(92)80072-u.
5
A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding.一种利用蛋白质 - 染料结合原理对微克级蛋白质进行定量的快速灵敏方法。
Anal Biochem. 1976 May 7;72:248-54. doi: 10.1016/0003-2697(76)90527-3.
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