Biosynthèse du noyau naphtoquinonique des ménaquinones bactériennes

Abstract

Incorporation of some 14C‐ or 3H‐labeled compounds in menaquinones of various Gram + or Gram – bacteria has been tried during bacterial growth or with resting cells of Mycobacterium phlei, Mycobacterium avium, Bacillus megaterium, Micrococcus lysodeikticus, Aerobacter aerogenes, and Proteus vulgaris. [14C]p‐Hydroxybenzaldehyde and [3H]3,4‐dihydroxybenzaldehyde are not incorporated into the menaquinones; [14C‐ring labeled]p‐hydroxybenzaldehyde is incorporated into ubiquinone‐8 of P. vulgaris. [U‐14C]shikimic acid (or [1,2‐14C2]shikimic acid) are good precursors of the naphthoquinone ring of M. phlei menaquinone. Only a slight incorporation of [1‐14C]α‐naphthol into menaquinones could be demonstrated, except with a mutant strain of A. aerogenes which incorporated also with a high yield [14C]2‐methyl‐1,4‐naphthoquinone and [14C]1,4‐naphthoquinone. A comparison of radioactivity dilutions of these precursors indicated that menadione is probably not a true intermediate in menaquinone biosynthesis.

Isolation and identification of menaquinone-9 from purified nitrate reductase of Escherichia coli

“…Oxidation of a naphthoquinone of the menaquinone type with KMnO 4 should yield phthalic acid and levulinic acid; levulinic acid is an oxidation product of the side chain of any polyisoprenoid quinone (20), while phthalic acid would be produced from naphthoquinones, but not benzoquinones, by KMnO 4 oxidation (15,17,20). When fraction FIII was treated with KMnO 4 and the products of the reaction were separated by ion-pair reverse-phase HPLC (Fig.…”

Biosynthesis of vitamin K (menaquinone) in bacteria.

“…The possible role of 3,4-dihydroxybenzaldehyde has remained enigmatic. Radioactive samples of 3,4-dihydroxybenzaldehyde and the corresponding acid were not incorporated into menaquinones by cultures of E. coli, Mycobacterium phlei, Bacillus megaterium, Proteus vulgaris, and "A. aerogenes" (43,44,83,135).…”

“…However, despite these chemical degradations, it now appears most probable that the menaquinone samples in this work were contaminated with impurities that were difficult to remove. Using more rigorous purifications, other workers have failed to show conversion of 1naphthol to menaquinone in Mycobacterium phlei, "Micrococcus lysodeikticus," Bacillus megaterium (several strains, including that used by Zenk and his colleagues), Proteus vulgaris, and Proteus mirabilis (21,35,44,64,83).…”

Effect of Menadiol Disulfate on the Phylloquinone Content of Wheat (Triticum aestivum)

“…The results are consistent with recent findings of Lichtenthaler et al (1971) who showed that menadione (2-methyl-l,4-naphthoquinone) induces an increased synthesis of phylloquinone in excised etiolated barley shoots {Hordeum vulgare L.) in the dark. Furthermore, Martius and Leuzinger (1964) and Guerin et al (1970) have shown menadione to be incorporated into bacterial menaquinones (2-methyl-3-multiprenyl-l ,4-naphthoquinones). Fiowever, the discovery of 2-demethylphylloquinone in spinach {Spinacia oleracea L.) chloroplasts (Mc-Kenna et al 1964) indicates that the attachment of the Physiol.…”