Hydroxyl regioisomerization of anthracycline catalyzed by a four-enzyme cascade

Proceedings of the National Academy of Sciences of the United States of America

Volumn 114, Issue 7, 2017, Pages 1554-1559

  Zhang, Zhuan ^a   Gong, Yu Kang ^a   Zhou, Qiang ^a   Hu, Yu ^a   Ma, Hong Min ^a   Chen, Yong Sheng ^a   Igarashi, Yasuhiro ^b   Pan, Lifeng ^a   Tang, Gong Li ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b TOYAMA PREFECTURAL UNIVERSITY   (Japan)

Author keywords

Biosynthesis; C 4 deoxyanthracycline; Dehydroxylation; NmrA like short chain dehydrogenase; Two component hydroxylase

Indexed keywords

ANTHRACYCLINE ANTIBIOTIC AGENT; ANTHRAQUINONE DERIVATIVE; ENZYME; HYDROXYL GROUP; KOSINOSTATIN; UNCLASSIFIED DRUG; AMINOGLYCOSIDE; ANTHRACYCLINE; BACTERIAL PROTEIN;

ANTIBIOTIC BIOSYNTHESIS; AROMATIZATION; ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; DRUG HYDROXYLATION; IN VITRO STUDY; ISOMERIZATION; NONHUMAN; PRIORITY JOURNAL; BIOCATALYSIS; BIOSYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; GENETICS; METABOLISM; MICROMONOSPORA; MOLECULAR MODEL; MUTATION; PROTEIN DOMAIN; STEREOISOMERISM;

AMINOGLYCOSIDES; ANTHRACYCLINES; BACTERIAL PROTEINS; BIOCATALYSIS; BIOSYNTHETIC PATHWAYS; ENZYMES; MICROMONOSPORA; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MUTATION; PROTEIN DOMAINS; STEREOISOMERISM;

EID: 85012981871     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1610097114     Document Type: Article

References (33)

1. Minotti G, Menna P, Salvatorelli E, Cairo G, Gianni L (2004) Anthracyclines: Molecular advances and pharmacologic developments in antitumor activity and cardiotoxicity. Pharmacol Rev 56(2):185-229.
2. Zhang G, et al. (2005) Syntheses and biological activities of disaccharide daunorubicins. J Med Chem 48(16):5269-5278.
3. Metsä-Ketelä M, Niemi J, Mäntsälä P, Schneider G (2008) Anthracycline biosynthesis: Genes, enzymes, and mechanisms. Top Curr Chem 282:101-140.
4. Shen B (2000) Biosynthesis of aromatic polyketides. Top Curr Chem 209:1-51.
5. Hertweck C, Luzhetskyy A, Rebets Y, Bechthold A (2007) Type II polyketide synthases: Gaining a deeper insight into enzymatic teamwork. Nat Prod Rep 24(1):162-190.
6. Das A, Khosla C (2009) Biosynthesis of aromatic polyketides in bacteria. Acc Chem Res 42(5):631-639.
7. Zhou H, Li Y, Tang Y (2010) Cyclization of aromatic polyketides from bacteria and fungi. Nat Prod Rep 27(6):839-868.
8. Niemi J, Metsä-Ketelä M, Schneider G, Mäntsälä P (2008) Biosynthetic anthracycline variants. Top Curr Chem 282:75-99.
9. Rix U, Fischer C, Remsing LL, Rohr J (2002) Modification of post-PKS tailoring steps through combinatorial biosynthesis. Nat Prod Rep 19(5):542-580.
10. Olano C, Méndez C, Salas JA (2010) Post-PKS tailoring steps in natural product-producing actinomycetes from the perspective of combinatorial biosynthesis. Nat Prod Rep 27(4):571-616.
11. Furumai T, Igarashi Y, Higuchi H, Saito N, Oki T (2002) Kosinostatin, a quinocycline antibiotic with antitumor activity from Micromonospora sp. TP-A0468. J Antibiot (Tokyo) 55(2):128-133.
12. Ma HM, et al. (2013) Unconventional origin and hybrid system for construction of pyrrolopyrrole moiety in kosinostatin biosynthesis. Chem Biol 20(6):796-805.
13. Beinker P, et al. (2006) Crystal structures of SnoaL2 and AclR: Two putative hydroxylases in the biosynthesis of aromatic polyketide antibiotics. J Mol Biol 359(3):728-740.
14. Oki T, et al. (1979) Antitumor anthracycline antibiotics, aclacinomycin a and analogues. II. Structural determination. J Antibiot (Tokyo) 32(8):801-819.
15. Siitonen V, Blauenburg B, Kallio P, Mäntsälä P, Metsä-Ketelä M (2012) Discovery of a two-component monooxygenase SnoaW/SnoaL2 involved in nogalamycin biosynthesis. Chem Biol 19(5):638-646.
16. Unciuleac M, Warkentin E, Page CC, Boll M, Ermler U (2004) Structure of a xanthine oxidase-related 4-hydroxybenzoyl-CoA reductase with an additional [4Fe-4S] cluster and an inverted electron flow. Structure 12(12):2249-2256.
17. Boll M (2005) Key enzymes in the anaerobic aromatic metabolism catalysing Birch-like reductions. Biochim Biophys Acta 1707(1):34-50.
18. Basarab GS, et al. (1999) Catalytic mechanism of scytalone dehydratase: Site-directed mutagenisis, kinetic isotope effects, and alternate substrates. Biochemistry 38(19):6012-6024.
19. Thompson JE, et al. (2000) The second naphthol reductase of fungal melanin biosynthesis in Magnaporthe grisea: Tetrahydroxynaphthalene reductase. J Biol Chem 275(45):34867-34872.
20. Liao D, Basarab GS, Gatenby AA, Valent B, Jordan DB (2001) Structures of trihydroxynaphthalene reductase-fungicide complexes: Implications for structure-based design and catalysis. Structure 9(1):19-27.
21. Kavanagh KL, Jörnvall H, Persson B, Oppermann U (2008) Medium- and short-chain dehydrogenase/reductase gene and protein families : The SDR superfamily: Functional and structural diversity within a family of metabolic and regulatory enzymes. Cell Mol Life Sci 65(24):3895-3906.
22. Stammers DK, et al. (2001) The structure of the negative transcriptional regulator NmrA reveals a structural superfamily which includes the short-chain dehydrogenase/reductases. EMBO J 20(23):6619-6626.
23. Thoden JB, Holden HM (1998) Dramatic differences in the binding of UDP-galactose and UDP-glucose to UDP-galactose 4-epimerase from Escherichia coli. Biochemistry 37(33):11469-11477.
24. Zhang G, et al. (2014) Mechanistic insights into polycycle formation by reductive cyclization in ikarugamycin biosynthesis. Angew Chem Int Ed Engl 53(19):4840-4844.
25. Ye Q, et al. (2010) Construction and co-expression of a polycistronic plasmid encoding carbonyl reductase and glucose dehydrogenase for production of ethyl (S)-4-chloro-3-hydroxybutanoate. Bioresour Technol 101(17):6761-6767.
26. Adams N, et al. (1990) Synthesis and antitumor activity of novel 4-demethoxyanthracyclines. J Med Chem 33(9):2375-2379.
27. Eberlein C, et al. (2013) Identification and characterization of 2-naphthoyl-coenzyme A reductase, the prototype of a novel class of dearomatizing reductases. Mol Microbiol 88(5):1032-1039.
28. Zhuo CX, Zhang W, You SL (2012) Catalytic asymmetric dearomatization reactions. Angew Chem Int Ed Engl 51(51):12662-12686.
29. Wang DS, Chen QA, Lu SM, Zhou YG (2012) Asymmetric hydrogenation of heteroarenes and arenes. Chem Rev 112(4):2557-2590.
30. Schätzle MA, et al. (2012) Tetrahydroxynaphthalene reductase: Catalytic properties of an enzyme involved in reductive asymmetric naphthol dearomatization. Angew Chem Int Ed Engl 51(11):2643-2646.
31. Husain SM, Schätzle MA, Lüdeke S, Müller M (2014) Unprecedented role of hydronaphthoquinone tautomers in biosynthesis. Angew Chem Int Ed Engl 53(37):9806-9811.
32. Schätzle MA, Husain SM, Ferlaino S, Müller M (2012) Tautomers of anthrahydroquinones: Enzymatic reduction and implications for chrysophanol, monodictyphenone, and related xanthone biosyntheses. J Am Chem Soc 134(36):14742-14745.
33. Conradt D, Schätzle MA, Haas J, Townsend CA, Müller M (2015) New insights into the conversion of versicolorin A in the biosynthesis of aflatoxin B1. J Am Chem Soc 137(34):10867-10869.