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

Conference · Fri Jan 01 00:00:00 EST 1988

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 Laboratory (LANL), Los Alamos, NM (United States)
• DOE Contract Number: W-7405-ENG-36
• OSTI ID: 6486350
• Report Number(s): LA-UR-88-3540; CONF-8809195-1; ON: DE89002354
• Resource Relation: Conference: 1. international symposium on PQQ and quinoproteins, Delft, Netherlands, 5 Sep 1988; Other Information: Paper copy only, copy does not permit microfiche production
• Country of Publication: United States
• Language: English

Related Subjects

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