Arthur F. Wagner

Preparation of sepharose-bound poly (rI:rC)

Abstract Poly rI was covalently bound through its terminal 5′-phosphate moiety to Sepharose and then annealed with poly rC to yield insoluble matrix bound poly (rI:rC). The method has no serious deleterious effects on the integrity or in vitro biological activity of the double stranded complexes.

Vitamins and coenzymes

Vitamins and CoenzymesBy Dr. Arthur F. Wagner and Dr. Karl Folkers. Pp. xvi + 532. (New York and London: Interscience Publishers, a Division of John Wiley and Sons, 1964.) 132s.

COENZYME Q. 53. NOVEL FINDING OF ACTIVITY FOR HEXAHYDROCOENZYME Q4 IN THE DYSTROPHIC RABBIT.

Abstract Hexahydrocoenzyme Q 4 has cured rabbits of nutritionally induced dystrophy and has prevented appearance of dystrophy by prophylactic therapy. The data are novel for in vivo activity of a quinone member of the CoQ group since previous in vivo data were largely for a chromanol of CoQ. Since CoQ to date has been identified in nature as quinone rather than chromanol, the former deserves the emphasis although the latter has shown extensive biological activities.

Biological activities of compounds in the vitamin E, vitamin K and coenzyme Q groups in chicks, rabbits and rats.

Abstract The chromanol of hexahydrocoenzyme Q 4 was found to prevent encephalomalacia in the chick, the resorption-gestation syndrome in the rat, and to cure nutritional muscular dystrophy in the rabbit. The chromanol of vitamin K 1(20) also prevented encephalomalacia in the chick. Other compounds including hexahydrocoenzyme Q 4 , chromenols of hexahydrocoenzyme Q 4 and coenzyme Q 10 , and tocopheryl quinone were inactive in preventing encephalomalacia and the resorption-gestation syndrome. The chromanol of vitamin K 1(20) was effective in shortening prothrombin time in vitamin K-deficient rats, while the chromanol of hexahydrocoenzyme Q 4 and the chromenol of coenzyme Q 10 were ineffective.

Considerations of Veristic and Quasi-biological Activities for Coenzyme Q and Vitamins E and K

The coenzyme Q group of compounds was elucidated just over five years ago. Their biochemical significance received prompt attention in vitro, but biological research on experimental animals and medical research have progressed more slowly. As in vivo animal data become available, however, a new facet of activity relationships between coenzyme Q and vitamins E and K is apparent, and a new appraisal of the literature is timely. It has been well known that the activities of the coenzyme Q and vitamins E and K groups are shared by the several structurally related compounds in each group. Today, it becomes strikingly apparent that members of the coenzyme Q and vitamins E and K groups have certain biological activities in common. For example, coenzyme Q and vitamin K both function [i] as cofactors of a steroidal i-dehydrogenase; a-tocopherol and the 6-chromanol of hexahydrocoenzyme Q4 both greatly extend [2] the motility of sperm; a 6-chromanol of the coenzyme Q group is apparently active in preventing [3 ] the gestation-résorption syndrome in the tocopherol-deficient rat; and the 6-chromanol of hexahydrocoenzyme Q4 and a-tocopherol exhibit similar biological activity in the anemic and dystrophic monkey [4]. If these exemplary activities do not entirely reflect an antioxidant property or another non-specific functional characteristic of these compounds, the following question may be asked. When compounds of the E, K, and Q groups exhibit a similar biological activity, should the activity of each group be defined according to the intrinsic or extrinsic relationship of each group to the biological system? Considera-

Coenzyme Q. XXXIX. Studies on the biosynthesis of coenzyme Q10

Tritium-labeled coenzyme Q0 has been previously used to study the alkylation step in the biosynthesis of coenzyme Q. The reaction of tritium and coenzyme Q0 by the Wilzbach technique does not give a uniformly labeled product as previously assumed; the reaction product has over 99% of the tritium in the 6-position. Since this tritium would be displaced on alkylation, the product is not useful for a study of this step in the biosynthesis. Coenzyme Q0 (I), fumigatin (II), and 2,3-dihydroxy-t-methyl-1,4-benzohydroquinone (III) were selectively labeled with tritium in the 5-methyl substituent and studied as potential precursors in the microbial biosynthesis of coenzyme Q. None of these products was utilized by Pseudomonas denitrificans in the biosynthesis of coenzyme Q10.

Coenzyme Q. XLIII. The new 5-chloromethyl-6-chromanyl acetate of vitamin K1(20)

Abstract A new and unexpected 6-chromanyl derivative of vitamin K 1(20) has been isolated from an acetylated enzymic reaction mixture obtained after incubating vitamin K 1(20) in a light-inactivated, cell-free extract of Mycobacterium phlei . The structure of the new compound was established as the 5-chloromethyl-6-chromanyl acetate derivative I of vitamin K 1(20) ; its non-enzymic origin was confirmed later by chemical transformations of vitamin K 1(20) .