PQQ: Biosynthetic studies in Methylobacterium AM1 and Hyphomicrobium X using specific TC labeling and NMR. [Pyrroloquinoline quinones]

Conference · Thu Dec 31 23:00:00 EST 1987

OSTI ID:6486350

Houck, D R; Hanners, J L; Unkefer, C J; van Kleef, M A.G.; Duine, J A

Using TC labeling and NMR spectroscopy we have determined biosynthetic precursors of pyrroloquinoline quinone (PQQ) in two closely related serine-type methylotrophs, Methylobacterium AM1 and Hyphomicrobium X. Analysis of the TC-labeling data revealed that PQQ is constructed from two amino acids: the portion containing N-6, C-7,8,9 and the two carboxylic acid groups, C-7' and 9', is derived-intact-from glutamate. The remaining portion is derived from tyrosine; the phenol side chain provides the six carbons of the ring containing the orthoquinone, whereas internal cyclization of the amino acid backbone forms the pyrrole-2-carboxylic acid moiety. This is analogous to the cyclization of dopaquinone to form dopachrome. Dopaquinone is a product of the oxidation of tyrosine (via dopa) in reactions catalyzed by monophenol monooxygenase (EC 1.14.18.1). Starting with tyrosine and glutamate, we will discuss possible biosynthetic routes to PQQ. 29 refs., 4 figs., 2 tabs.

• Research Organization: Los Alamos National Lab., NM (USA)
• DOE Contract Number: W-7405-ENG-36
• OSTI ID: 6486350
• Report Number(s): LA-UR-88-3540; CONF-8809195-1; ON: DE89002354
• Country of Publication: United States
• Language: English

Related Subjects

550200 -- Biochemistry
550700* -- Microbiology
59 BASIC BIOLOGICAL SCIENCES
AMINO ACIDS
AROMATICS
BIOCHEMICAL REACTION KINETICS
BIOSYNTHESIS
CARBON 13
CARBON ISOTOPES
CARBOXYLIC ACIDS
CHEMICAL SHIFT
ENZYMES
EVEN-ODD NUCLEI
ISOTOPES
KINETICS
LABELLED COMPOUNDS
LIGHT NUCLEI
MICROORGANISMS
NMR SPECTRA
NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
QUINONES
REACTION KINETICS
SPECTRA
STABLE ISOTOPES
SYNTHESIS