Biosynthesis of the 2-(aminomethyl)-4-(hydroxymethyl)furan subunit of methanofuran

Journal Article · Tue Jun 14 00:00:00 EDT 1988 · Biochemistry; (United States)

DOI:https://doi.org/10.1021/bi00412a031· OSTI ID:6905713

White, R H

/sup 2/H- and /sup 13/C-labeled precursors were used to establish the pathway for the biosynthesis of the 2-(aminomethyl)-4-(hydroxymethyl)furan (F1) component of methanofuran in methanogenic archaebacteria. The extent and position of the label incorporated into F1 were measured from the mass spectrum of the diacetyl derivative of F1. (1,2-/sup 13/C/sub 2/)Acetate was found to be incorporated into two separate positions of the F1 molecule as a unit. The extent of incorporation of /sup 13/C/sub 2/ into each of these positions was the same as that observed for the incorporation of acetate into the alanine and proline produced by the cells. From (2,2,2-/sup 2/H/sub 3/)acetate, deuterium was incorporated into two separate sites of the F1 molecule, one containing up to two deuteriums and the other only one. On the basis of the fragmentation pattern of the F1 diacetyl derivative, it was determined that two deuteriums were incorporated into the hydroxymethyl group at C-4 and one was incorporated at C-3 of the furan ring. The extent and distribution of the incorporated deuterium at the C-4 methylene were the same as that observed for C-6 of the glucose produced by the cells. On the basis of this and additional information presented in this paper, it is concluded that F1 is generated by the condensation of dihydroxyacetone phosphate with pyruvate. The resulting dihydroxy-substituted tetrahydrofuran after elimination of 2 mol of water would produce the phosphate ester of 2-carboxy-4-(hydroxymethyl)furan. Reduction of the carboxylic acid to an aldehyde and subsequent transamination would produce the phosphate ester of F1.

• Research Organization: Virginia Polytechnic Institute and State Univ., Blacksburg (USA)
• OSTI ID: 6905713
• Journal Information: Biochemistry; (United States), Vol. 27:12
• Country of Publication: United States
• Language: English

Related Subjects

59 BASIC BIOLOGICAL SCIENCES
FURANS
BIOSYNTHESIS
LABELLED COMPOUNDS
ACETATES
CARBON 13
DEUTERIUM COMPOUNDS
GAS CHROMATOGRAPHY
MASS SPECTROSCOPY
METHANOGENIC BACTERIA
BACTERIA
CARBON ISOTOPES
CARBOXYLIC ACID SALTS
CHROMATOGRAPHY
EVEN-ODD NUCLEI
HETEROCYCLIC COMPOUNDS
HYDROGEN COMPOUNDS
ISOTOPES
LIGHT NUCLEI
MICROORGANISMS
NUCLEI
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
SEPARATION PROCESSES
SPECTROSCOPY
STABLE ISOTOPES
SYNTHESIS
550201* - Biochemistry- Tracer Techniques