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. 1992 Jul;174(14):4576–4582. doi: 10.1128/jb.174.14.4576-4582.1992

5-(p-aminophenyl)-1,2,3,4-tetrahydroxypentane, a structural component of the modified folate in Sulfolobus solfataricus.

D Zhou 1, R H White 1
PMCID: PMC206252  PMID: 1320614

Abstract

The partial characterization of the modified folate present in Sulfolobus solfataricus has been carried out. Separation of ethanol-water extracts of these cells on a DEAE-Sephadex column led to the isolation of a small amount of intact oxidized cofactor, which, when subjected to reductive cleavage with Zn-HCl, produced 6-methylpterin. This indicated that the modified folate in these cells contained a nonmethylated pterin linked, via a methylene group at the C-6 position of the pterin, to an arylamine, as is found in folate. Oxidative cleavage of intact reduced cofactor produced pterin and a single arylamine. The azo dye derivative of this arylamine was prepared and purified by chromatography on a Bio-Gel P-6 column. The resulting purified compound was shown to be readily hydrolyzed in dilute acid to the azo dye derivative of 5-(p-aminophenyl)-1,2,3,4-tetrahydroxypantane, which was, in turn, readily cleaved to 5-(p-aminophenyl)-1,2,3,4- tetrahydroxypentane by Zn-HCl reduction. The stereochemistry of the resulting 5-(p-aminophenyl)-1,2,3,4-tetrahydroxypentane was shown to be ribo, the same as that of the 5-(p-aminophenyl)-1,2,3,4- tetrahydroxypentane moiety found in methanopterin. The complete arylamine side chain of the modified folate thus contains 5-(p-aminophenyl)-1,2,3,4-tetrahydroxypentane attached, via an acid-labile bond, to a currently unidentified substituent. The modified folate present in S. solfataricus thus contains structural features common to both folates and methanopterin.

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Selected References

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  1. Brody T., Shane B., Stokstad E. L. Separation and identification of pteroylpolyglutamates by polyacrylamide gel chromatography. Anal Biochem. 1979 Jan 15;92(2):501–509. doi: 10.1016/0003-2697(79)90691-2. [DOI] [PubMed] [Google Scholar]
  2. Foo S. K., Cichowicz D. J., Shane B. Cleavage of naturally occurring folates to unsubstituted p-aminobenzoylpoly-gamma-glutamates. Anal Biochem. 1980 Sep 1;107(1):109–115. doi: 10.1016/0003-2697(80)90499-6. [DOI] [PubMed] [Google Scholar]
  3. Keltjens J. T., Rozie H. J., Vogels G. D. Identification of 6-acetyl-7-methyl-7,8-dihydropterin as a degradation product of 5,10-methenyl-5,6,7,8-tetrahydromethanopterin. Arch Biochem Biophys. 1984 Mar;229(2):532–537. doi: 10.1016/0003-9861(84)90184-x. [DOI] [PubMed] [Google Scholar]
  4. Lin X. L., White R. H. Structure of solfapterin (erythro-neopterin-3'-D-2-deoxy-2-aminoglucopyranoside) isolated from the thermophilic archaebacterium Sulfolobus solfataricus. J Bacteriol. 1988 Mar;170(3):1396–1398. doi: 10.1128/jb.170.3.1396-1398.1988. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Raemakers-Franken P. C., Bongaerts R., Fokkens R., van der Drift C., Vogels G. D. Characterization of two pterin derivatives isolated from Methanoculleus thermophilicum. Eur J Biochem. 1991 Sep 15;200(3):783–787. doi: 10.1111/j.1432-1033.1991.tb16245.x. [DOI] [PubMed] [Google Scholar]
  6. Raemakers-Franken P. C., Voncken F. G., Korteland J., Keltjens J. T., van der Drift C., Vogels G. D. Structural characterization of tatiopterin, a novel pterin isolated from Methanogenium tationis. Biofactors. 1989 Dec;2(2):117–122. [PubMed] [Google Scholar]
  7. Shane B. Identification of folylpoly(gamma-glutamate) chain length by cleavage to and separation of p-aminobenzoylpoly(gamma-glutamates). Methods Enzymol. 1986;122:323–330. doi: 10.1016/0076-6879(86)22188-6. [DOI] [PubMed] [Google Scholar]
  8. White R. H. 7-Methylpterin and 7-methyllumizine: oxidative degradation products of 7-methyl-substituted pteridines in methanogenic bacteria. J Bacteriol. 1985 May;162(2):516–520. doi: 10.1128/jb.162.2.516-520.1985. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. White R. H. Analysis and characterization of the folates in the nonmethanogenic archaebacteria. J Bacteriol. 1988 Oct;170(10):4608–4612. doi: 10.1128/jb.170.10.4608-4612.1988. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. White R. H. Distribution of folates and modified folates in extremely thermophilic bacteria. J Bacteriol. 1991 Mar;173(6):1987–1991. doi: 10.1128/jb.173.6.1987-1991.1991. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Woese C. R., Kandler O., Wheelis M. L. Towards a natural system of organisms: proposal for the domains Archaea, Bacteria, and Eucarya. Proc Natl Acad Sci U S A. 1990 Jun;87(12):4576–4579. doi: 10.1073/pnas.87.12.4576. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. van Beelen P., Labro J. F., Keltjens J. T., Geerts W. J., Vogels G. D., Laarhoven W. H., Guijt W., Haasnoot C. A. Derivatives of methanopterin, a coenzyme involved in methanogenesis. Eur J Biochem. 1984 Mar 1;139(2):359–365. doi: 10.1111/j.1432-1033.1984.tb08014.x. [DOI] [PubMed] [Google Scholar]
  13. van Beelen P., Stassen A. P., Bosch J. W., Vogels G. D., Guijt W., Haasnoot C. A. Elucidation of the structure of methanopterin, a coenzyme from Methanobacterium thermoautotrophicum, using two-dimensional nuclear-magnetic-resonance techniques. Eur J Biochem. 1984 Feb 1;138(3):563–571. doi: 10.1111/j.1432-1033.1984.tb07951.x. [DOI] [PubMed] [Google Scholar]

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