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Biosynthèse du noyau naphtoquinonique des ménaquinones bactériennes

1970; Wiley; Volume: 15; Issue: 3 Linguagem: Inglês

10.1111/j.1432-1033.1970.tb01024.x

1432-1033

Marcelo E. Guerin, Mireille Leduc, Robert Azerad,

Chemistry and Chemical Engineering

Incorporation of some 14 C‐ or 3 H‐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 . [ 14 C] p ‐Hydroxybenzaldehyde and [ 3 H]3,4‐dihydroxybenzaldehyde are not incorporated into the menaquinones; [ 14 C‐ring labeled] p ‐hydroxybenzaldehyde is incorporated into ubiquinone‐8 of P. vulgaris . [U‐ 14 C]shikimic acid (or [1,2‐ 14 C 2 ]shikimic acid) are good precursors of the naphthoquinone ring of M. phlei menaquinone. Only a slight incorporation of [1‐ 14 C]α‐naphthol into menaquinones could be demonstrated, except with a mutant strain of A. aerogenes which incorporated also with a high yield [ 14 C]2‐methyl‐1,4‐naphthoquinone and [ 14 C]1,4‐naphthoquinone. A comparison of radioactivity dilutions of these precursors indicated that menadione is probably not a true intermediate in menaquinone biosynthesis.