Biosynthesis of pyrroloquinoline quinone. 1. Identification of biosynthetic precursors using /sup 13/C labeling and NMR spectroscopy

Journal Article · Wed Sep 28 00:00:00 EDT 1988 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00228a070· OSTI ID:5913998

Houck, D R; Hanners, J L; Unkefer, C J

The biosynthesis of pyrroloquinoline quinone (PQQ) in the methylotropic bacterium methylobacterium AM1 has been investigated using /sup 13/C-labelling of the products and NMR spectroscopy. The data indicated that the quinoline portion of PQQ is formed by a novel condensation of N-1, C-2, -3, and -4 of glutamate with a symmetrical six-carbon ring derived from the shikimate pathway. It is postulated that tyrosine is the shikimate-derived percursor, since pyrrole could be formed by the internal cyclization of the amino acid backbone. 18 references, 2 figures, 2 tables.

• Research Organization: Los Alamos National Lab., NM (USA)
• OSTI ID: 5913998
• Journal Information: J. Am. Chem. Soc.; (United States), Vol. 110:20
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
PYRROLES
BIOSYNTHESIS
QUINOLINES
QUINONES
CARBON 13
LABELLED COMPOUNDS
NMR SPECTRA
TRACER TECHNIQUES
AROMATICS
AZAARENES
AZINES
AZOLES
CARBON ISOTOPES
EVEN-ODD NUCLEI
HETEROCYCLIC COMPOUNDS
ISOTOPE APPLICATIONS
ISOTOPES
LIGHT NUCLEI
NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PYRIDINES
SPECTRA
STABLE ISOTOPES
SYNTHESIS
400201* - Chemical & Physicochemical Properties