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Flavoenzyme-catalyzed formation of disulfide bonds in natural products.

Scharf DH, Groll M, Habel A, Heinekamp T, Hertweck C, Brakhage AA, Huber EM
Angew Chem Int Ed Engl 53 2221-4 (2014)
Related entries: 4ntc, 4nte

Cited: 17 times
EuropePMC logo PMID: 24446392

Abstract

Nature provides a rich source of compounds with diverse chemical structures and biological activities, among them, sulfur-containing metabolites from bacteria and fungi. Some of these compounds bear a disulfide moiety that is indispensable for their bioactivity. Specialized oxidoreductases such as GliT, HlmI, and DepH catalyze the formation of this disulfide bridge in the virulence factor gliotoxin, the antibiotic holomycin, and the anticancer drug romidepsin, respectively. We have examined all three enzymes by X-ray crystallography and activity assays. Despite their differently sized substrate binding clefts and hence, their diverse substrate preferences, a unifying reaction mechanism is proposed based on the obtained crystal structures and further supported by mutagenesis experiments.

Articles - 4ntd mentioned but not cited (1)

  1. Unprecedented pathway of reducing equivalents in a diflavin-linked disulfide oxidoreductase. Buey RM, Arellano JB, López-Maury L, Galindo-Trigo S, Velázquez-Campoy A, Revuelta JL, de Pereda JM, Florencio FJ, Schürmann P, Buchanan BB, Balsera M. Proc Natl Acad Sci U S A 114 12725-12730 (2017)


Reviews citing this publication (4)

  1. Oxidative Cyclization in Natural Product Biosynthesis. Tang MC, Zou Y, Watanabe K, Walsh CT, Tang Y. Chem Rev 117 5226-5333 (2017)
  2. Gliotoxin--bane or boon? Scharf DH, Brakhage AA, Mukherjee PK. Environ Microbiol 18 1096-1109 (2016)
  3. Epipolythiodioxopiperazine-Based Natural Products: Building Blocks, Biosynthesis and Biological Activities. Huber EM. Chembiochem 23 e202200341 (2022)
  4. Bispyrrolidinoindoline Epi(poly)thiodioxopiperazines (BPI-ETPs) and Simplified Mimetics: Structural Characterization, Bioactivities, and Total Synthesis. Martínez C, García-Domínguez P, Álvarez R, de Lera AR. Molecules 27 7585 (2022)

Articles citing this publication (12)

  1. Cs2 CO3 -Catalyzed Aerobic Oxidative Cross-Dehydrogenative Coupling of Thiols with Phosphonates and Arenes. Song S, Zhang Y, Yeerlan A, Zhu B, Liu J, Jiao N. Angew Chem Int Ed Engl 56 2487-2491 (2017)
  2. Identification and characterization of the verticillin biosynthetic gene cluster in Clonostachys rogersoniana. Wang Y, Hu P, Pan Y, Zhu Y, Liu X, Che Y, Liu G. Fungal Genet Biol 103 25-33 (2017)
  3. Gliotoxin: nature's way of making the epidithio bridge. Amatov T, Jahn U. Angew Chem Int Ed Engl 53 3312-3314 (2014)
  4. Identification of an unusual type II thioesterase in the dithiolopyrrolone antibiotics biosynthetic pathway. Zhai Y, Bai S, Liu J, Yang L, Han L, Huang X, He J. Biochem Biophys Res Commun 473 329-335 (2016)
  5. New insights into the disulfide bond formation enzymes in epidithiodiketopiperazine alkaloids. Liu H, Fan J, Zhang P, Hu Y, Liu X, Li SM, Yin WB. Chem Sci 12 4132-4138 (2021)
  6. Thiocysteine lyases as polyketide synthase domains installing hydropersulfide into natural products and a hydropersulfide methyltransferase. Meng S, Steele AD, Yan W, Pan G, Kalkreuter E, Liu YC, Xu Z, Shen B. Nat Commun 12 5672 (2021)
  7. Base-controlled Fe(Pc)-catalyzed aerobic oxidation of thiols for the synthesis of S-S and S-P(O) bonds. Huang H, Ash J, Kang JY. Org Biomol Chem 16 4236-4242 (2018)
  8. N-Heterocyclization in Gliotoxin Biosynthesis is Catalyzed by a Distinct Cytochrome P450 Monooxygenase. Scharf DH, Chankhamjon P, Scherlach K, Dworschak J, Heinekamp T, Roth M, Brakhage AA, Hertweck C. Chembiochem 22 336-339 (2021)
  9. Structural and Mechanistic Insights into C-S Bond Formation in Gliotoxin. Scherlach K, Kuttenlochner W, Scharf DH, Brakhage AA, Hertweck C, Groll M, Huber EM. Angew Chem Int Ed Engl 60 14188-14194 (2021)
  10. Integration of In Silico and In Vitro Analysis of Gliotoxin Production Reveals a Narrow Range of Producing Fungal Species. Redrado S, Esteban P, Domingo MP, Lopez C, Rezusta A, Ramirez-Labrada A, Arias M, Pardo J, Galvez EM. J Fungi (Basel) 8 361 (2022)
  11. Characterization of sulfhydryl oxidase from Aspergillus tubingensis. Nivala O, Faccio G, Arvas M, Permi P, Buchert J, Kruus K, Mattinen ML. BMC Biochem 18 15 (2017)
  12. Tuning Selectivity in the Visible-Light-Promoted Coupling of Thiols with Alkenes by EDA vs TOCO Complex Formation. Das A, Thomas KRJ. ACS Omega 8 18275-18289 (2023)


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