Biosynthesis of nucleotide-activated D-glycero-D-manno-heptose - PubMed (original) (raw)

. 2001 Jun 15;276(24):20935-44.

doi: 10.1074/jbc.M100378200. Epub 2001 Mar 28.

Affiliations

• PMID: 11279237
• DOI: 10.1074/jbc.M100378200

Free article

Biosynthesis of nucleotide-activated D-glycero-D-manno-heptose

B Kneidinger et al. J Biol Chem. 2001.

Free article

Abstract

The glycan chain repeats of the S-layer glycoprotein of Aneurinibacillus thermoaerophilus DSM 10155 contain d-glycero-d-manno-heptose, which has also been described as constituent of lipopolysaccharide cores of Gram-negative bacteria. The four genes required for biosynthesis of the nucleotide-activated form GDP-d-glycero-d-manno-heptose were cloned, sequenced, and overexpressed in Escherichia coli, and the corresponding enzymes GmhA, GmhB, GmhC, and GmhD were purified to homogeneity. The isomerase GmhA catalyzed the conversion of d-sedoheptulose 7-phosphate to d-glycero-d-manno-heptose 7-phosphate, and the phosphokinase GmhB added a phosphate group to form d-glycero-d-manno-heptose 1,7-bisphosphate. The phosphatase GmhC removed the phosphate in the C-7 position, and the intermediate d-glycero-alpha-d-manno-heptose 1-phosphate was eventually activated with GTP by the pyrophosphorylase GmhD to yield the final product GDP-d-glycero-alpha-d-manno-heptose. The intermediate and end products were analyzed by high performance liquid chromatography. Nuclear magnetic resonance spectroscopy was used to confirm the structure of these substances. This is the first report of the biosynthesis of GDP-d-glycero-alpha-d-manno-heptose in Gram-positive organisms. In addition, we propose a pathway for biosynthesis of the nucleotide-activated form of l-glycero-d-manno-heptose.

PubMed Disclaimer

Similar articles

• Divergence of biochemical function in the HAD superfamily: D-glycero-D-manno-heptose-1,7-bisphosphate phosphatase (GmhB).
  Wang L, Huang H, Nguyen HH, Allen KN, Mariano PS, Dunaway-Mariano D. Wang L, et al. Biochemistry. 2010 Feb 16;49(6):1072-81. doi: 10.1021/bi902018y. Biochemistry. 2010. PMID: 20050615 Free PMC article.
• Biosynthesis of GDP-d-_glycero_-α-d-_manno_-heptose for the Capsular Polysaccharide of Campylobacter jejuni.
  Huddleston JP, Raushel FM. Huddleston JP, et al. Biochemistry. 2019 Sep 17;58(37):3893-3902. doi: 10.1021/acs.biochem.9b00548. Epub 2019 Aug 29. Biochemistry. 2019. PMID: 31449400 Free PMC article.
• Helicobacter pylori GmhB enzyme involved in ADP-heptose biosynthesis pathway is essential for lipopolysaccharide biosynthesis and bacterial virulence.
  Chiu SF, Teng KW, Wang PC, Chung HY, Wang CJ, Cheng HC, Kao MC. Chiu SF, et al. Virulence. 2021 Dec;12(1):1610-1628. doi: 10.1080/21505594.2021.1938449. Virulence. 2021. PMID: 34125649 Free PMC article.
• ADP-heptose: A new innate immune modulator.
  Hu X, Yang C, Wang PG, Zhang GL. Hu X, et al. Carbohydr Res. 2019 Feb 1;473:123-128. doi: 10.1016/j.carres.2018.12.011. Epub 2018 Dec 19. Carbohydr Res. 2019. PMID: 30684847 Review.
• Novel pathways for biosynthesis of nucleotide-activated glycero-manno-heptose precursors of bacterial glycoproteins and cell surface polysaccharides.
  Valvano MA, Messner P, Kosma P. Valvano MA, et al. Microbiology (Reading). 2002 Jul;148(Pt 7):1979-1989. doi: 10.1099/00221287-148-7-1979. Microbiology (Reading). 2002. PMID: 12101286 Review. No abstract available.

Cited by

• Relationship of Yersinia pseudotuberculosis O antigens IA, IIA, and IVB: the IIA gene cluster was derived from that of IVB.
  Pacinelli E, Wang L, Reeves PR. Pacinelli E, et al. Infect Immun. 2002 Jun;70(6):3271-6. doi: 10.1128/IAI.70.6.3271-3276.2002. Infect Immun. 2002. PMID: 12011023 Free PMC article.
• Chemoenzymatic synthesis of ADP-d-glycero-β-d-manno-heptose and study of the substrate specificity of HldE.
  Li T, Wen L, Williams A, Wu B, Li L, Qu J, Meisner J, Xiao Z, Fang J, Wang PG. Li T, et al. Bioorg Med Chem. 2014 Feb 1;22(3):1139-47. doi: 10.1016/j.bmc.2013.12.019. Epub 2013 Dec 19. Bioorg Med Chem. 2014. PMID: 24412338 Free PMC article.
• Structural genomics of enzymes involved in sterol/isoprenoid biosynthesis.
  Bonanno JB, Edo C, Eswar N, Pieper U, Romanowski MJ, Ilyin V, Gerchman SE, Kycia H, Studier FW, Sali A, Burley SK. Bonanno JB, et al. Proc Natl Acad Sci U S A. 2001 Nov 6;98(23):12896-901. doi: 10.1073/pnas.181466998. Proc Natl Acad Sci U S A. 2001. PMID: 11698677 Free PMC article.
• Identification of potential Leptospira phosphoheptose isomerase inhibitors through virtual high-throughput screening.
  Umamaheswari A, Pradhan D, Hemanthkumar M. Umamaheswari A, et al. Genomics Proteomics Bioinformatics. 2010 Dec;8(4):246-55. doi: 10.1016/S1672-0229(10)60026-5. Genomics Proteomics Bioinformatics. 2010. PMID: 21382593 Free PMC article.
• Potentiating Activity of GmhA Inhibitors on Gram-Negative Bacteria.
  Moreau F, Atamanyuk D, Blaukopf M, Barath M, Herczeg M, Xavier NM, Monbrun J, Airiau E, Henryon V, Leroy F, Floquet S, Bonnard D, Szabla R, Brown C, Junop MS, Kosma P, Gerusz V. Moreau F, et al. J Med Chem. 2024 Apr 25;67(8):6610-6623. doi: 10.1021/acs.jmedchem.4c00037. Epub 2024 Apr 10. J Med Chem. 2024. PMID: 38598312 Free PMC article.

Publication types

MeSH terms

Substances

LinkOut - more resources

• Full Text Sources

  • Elsevier Science

• Other Literature Sources

  • The Lens - Patent Citations Database

• Molecular Biology Databases

  • BioCyc

• Miscellaneous

  • NCI CPTAC Assay Portal