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

Abstract

/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,more » 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.« less

Authors:
Publication Date:
Research Org.:
Virginia Polytechnic Institute and State Univ., Blacksburg (USA)
OSTI Identifier:
6905713
Resource Type:
Journal Article
Journal Name:
Biochemistry; (United States)
Additional Journal Information:
Journal Volume: 27:12
Country of Publication:
United States
Language:
English
Subject:
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

Citation Formats

White, R H. Biosynthesis of the 2-(aminomethyl)-4-(hydroxymethyl)furan subunit of methanofuran. United States: N. p., 1988. Web. doi:10.1021/bi00412a031.
White, R H. Biosynthesis of the 2-(aminomethyl)-4-(hydroxymethyl)furan subunit of methanofuran. United States. https://doi.org/10.1021/bi00412a031
White, R H. 1988. "Biosynthesis of the 2-(aminomethyl)-4-(hydroxymethyl)furan subunit of methanofuran". United States. https://doi.org/10.1021/bi00412a031.
@article{osti_6905713,
title = {Biosynthesis of the 2-(aminomethyl)-4-(hydroxymethyl)furan subunit of methanofuran},
author = {White, R H},
abstractNote = {/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.},
doi = {10.1021/bi00412a031},
url = {https://www.osti.gov/biblio/6905713}, journal = {Biochemistry; (United States)},
number = ,
volume = 27:12,
place = {United States},
year = {Tue Jun 14 00:00:00 EDT 1988},
month = {Tue Jun 14 00:00:00 EDT 1988}
}