Evidence for a cytochrome P-450-catalyzed allylic rearrangement with double-bond topomerization

1988 ◽  
Vol 110 (6) ◽  
pp. 1979-1981 ◽  
Author(s):  
Robert H. McClanahan ◽  
Alain C. Huitric ◽  
Paul G. Pearson ◽  
John C. Desper ◽  
Sidney D. Nelson
Keyword(s):  
Double Bond ◽  
Allylic Rearrangement ◽  
Cytochrome P 450

Microbial hydroxylation of steroids. 10. Rearrangement during epoxidation and hydroxylation, and the stepwise nature of these enzymic reactions

1985 ◽  
Vol 63 (5) ◽  
pp. 1121-1126 ◽  
Author(s):  
Herbert L. Holland ◽  
Elly Riemland
Keyword(s):  
Double Bond ◽  
Product Formation ◽  
Enzymatic Oxidation ◽  
Allylic Rearrangement ◽  
Stepwise Mechanism ◽  
Microbial Hydroxylation ◽  
A Site

A series of unsaturated steroids has been incubated with fungi which are known to hydroxylate at a site corresponding to the allylic position in the analogous saturated steroids. In some cases, the anticipated hydroxylation occurred without rearrangement of the double bond. In a number of instances, however, products were obtained whose structures implied that allylic rearrangement had occurred during the reaction. The formation of these products is consistent with a stepwise mechanism of enzymatic oxidation. Possible routes for product formation are presented which incorporate this proposal.

Reevaluation of the stereochemical courses of the allylic rearrangement and the double-bond reduction catalyzed by Brevibacterium ammoniagenes fatty acid synthase

1991 ◽  
Vol 113 (10) ◽  
pp. 3997-3998 ◽  
Author(s):  
Mary C. O'Sullivan ◽  
John M. Schwab ◽  
T. Mark Zabriskie ◽  
Gregory L. Helms ◽  
John C. Vederas
Keyword(s):  
Fatty Acid ◽  
Double Bond ◽  
Fatty Acid Synthase ◽  
Allylic Rearrangement

Cu(I)-Catalyzed Coupling of (9-Benzylpurin-6-yl)magnesium Chloride with Allyl Halides: An Approach to 6-Allylpurine Derivatives

2006 ◽  
Vol 71 (8) ◽  
pp. 1221-1228 ◽  
Author(s):  
Martin Klečka ◽  
Tomáš Tobrman ◽  
Dalimil Dvořák
Keyword(s):  
Double Bond ◽  
Magnesium Chloride ◽  
Allylic Rearrangement ◽  
Allyl Halides ◽  
Purine Ring

6-Allylpurine derivatives are formed by Cu(I)-catalyzed coupling of (9-benzyl-9H-purin-6-yl)- magnesium chloride with allyl halides. The reaction is accompanied by allylic rearrangement in some cases. Under acid conditions the double bond of the allyl group rearranges to the conjugation with purine ring.

Ultrastructure and Drug Metabolism in the Developing Guinea Pig

1973 ◽  
Vol 31 ◽  
pp. 538-539
Author(s):  
W. Kuenzig ◽  
M. Boublik ◽  
J.J. Kamm ◽  
J.J. Burns
Keyword(s):  
Guinea Pig ◽  
Metabolic Activity ◽  
Animal Species ◽  
Adult Animal ◽  
Smooth Endoplasmic Reticulum ◽  
Fetal Life ◽  
Mixed Function Oxidase ◽  
Cytochrome P 450 ◽  
Microsomal Mixed Function Oxidase ◽  
Mixed Function Oxidase Activity

Unlike a variety of other animal species, such as the rabbit, mouse or rat, the guinea pig has a relatively long gestation period and is a more fully developed animal at birth. Kuenzig et al. reported that drug metabolic activity which increases very slowly during fetal life, increases rapidly after birth. Hepatocytes of a 3-day old neonate metabolize drugs and reduce cytochrome P-450 at a rate comparable to that observed in the adult animal. Moreover the administration of drugs like phenobarbital to pregnant guinea pigs increases the microsomal mixed function oxidase activity already in the fetus.Drug metabolic activity is, generally, localized within the smooth endoplasmic reticulum (SER) of the hepatocyte.

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