Recent advances in the elucidation of enzymatic function in natural product biosynthesis

F1000Research

Volumn 4, Issue , 2016, Pages

  Tan, Gao Yi ^a   Deng, Zixin ^a,b   Liu, Tiangang ^a,b  

^a WUHAN UNIVERSITY   (China)

^b Wuhan Institute of Biotechnology   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; ARTEMISINIC ACID; BE 7585A; CARBAPENEM; CODEINE; ETOPOSIDE; HYDROCODONE; HYDROMORPHONE; LINCOMYCIN; MAGNOFLORINE; MORPHINE; NATURAL PRODUCT; OPIATE; OXYCODONE; PIKROMYCIN; TETRAHYDROPAPAVEROLINE; UNCLASSIFIED DRUG; VANCOMYCIN;

ANALGESIA; BERBERIDACEAE; COMBINATORIAL LIBRARY; CONTROLLED STUDY; DRUG STRUCTURE; ENVIRONMENTAL FACTOR; ENZYME ACTIVITY; PALLIATIVE THERAPY; PAPAVER SOMNIFERUM; PAPAVERACEAE; REVIEW;

EID: 84964483286     PISSN: 20461402     EISSN: 1759796X     Source Type: Journal    
DOI: 10.12688/f1000research.7187.2     Document Type: Review

References (54)

1. Kinghorn AD Pan L Fletcher JN: The relevance of higher plants in lead compound discovery programs. J Nat Prod. 2011;74(6):1539-55. 21650152 10.1021/np200391c 3158731
2. Bérdy J: Bioactive microbial metabolites. J Antibiot (Tokyo). 2005;58(1):1-26. 15813176 10.1038/ja.2005.1
3. Hien TT White NJ: Qinghaosu. Lancet. 1993;341(8845):603-8. 8094838 10.1016/0140-6736(93)90362-K
4. Paddon CJ Westfall PJ Pitera DJ: High-level semi-synthetic production of the potent antimalarial artemisinin. Nature. 2013;496(7446):528-32. 23575629 10.1038/nature12051 F1000 Recommendation
5. PATH: Stabilizing the antimalarial drug supply: Semisynthetic artemisinin could meet up to one-third of global need.2014. Reference Source
6. Paddon CJ Keasling JD: Semi-synthetic artemisinin: a model for the use of synthetic biology in pharmaceutical development. Nat Rev Microbiol. 2014;12(5):355-67. 24686413 10.1038/nrmicro3240
7. Galanie S Thodey K Trenchard IJ: Complete biosynthesis of opioids in yeast. Science. 2015;349(6252):1095-100. 26272907 10.1126/science.aac9373 F1000 Recommendation
8. Service RF: SYNTHETIC BIOLOGY. Modified yeast produce opiates from sugar. Science. 2015;349(6249):677. 26273032 10.1126/science.349.6249.677
9. Mercke P Bengtsson M Bouwmeester HJ: Molecular cloning, expression, and characterization of amorpha-4,11-diene synthase, a key enzyme of artemisinin biosynthesis in Artemisia annua L. Arch Biochem Biophys. 2000;381(2):173-80. 11032404 10.1006/abbi.2000.1962 F1000 Recommendation
10. Martin VJ Pitera DJ Withers ST: Engineering a mevalonate pathway in Escherichia coli for production of terpenoids. Nat Biotechnol. 2003;21(7):796-802. 12778056 10.1038/nbt833 F1000 Recommendation
11. Ro DK Paradise EM Ouellet M: Production of the antimalarial drug precursor artemisinic acid in engineered yeast. Nature. 2006;440(7086):940-3. 16612385 10.1038/nature04640 F1000 Recommendation
12. Westfall PJ Pitera DJ Lenihan JR: Production of amorphadiene in yeast, and its conversion to dihydroartemisinic acid, precursor to the antimalarial agent artemisinin. Proc Natl Acad Sci U S A. 2012;109(3):E111-8. 22247290 10.1073/pnas.1110740109 3271868 F1000 Recommendation
13. Endy D: Foundations for engineering biology. Nature. 2005;438(7067):449-53. 16306983 10.1038/nature04342
14. Minami H Kim JS Ikezawa N: Microbial production of plant benzylisoquinoline alkaloids. Proc Natl Acad Sci U S A. 2008;105(21):7393-8. 18492807 10.1073/pnas.0802981105 2396723
15. Hawkins KM Smolke CD: Production of benzylisoquinoline alkaloids in Saccharomyces cerevisiae. Nat Chem Biol. 2008;4(9):564-73. 18690217 10.1038/nchembio.105 2830865
16. Nakagawa A Minami H Kim JS: A bacterial platform for fermentative production of plant alkaloids. Nat Commun. 2011;2: 326. 21610729 10.1038/ncomms1327 3112539 F1000 Recommendation
17. DeLoache WC Russ ZN Narcross L: An enzyme-coupled biosensor enables (S)-reticuline production in yeast from glucose. Nat Chem Biol. 2015;11(7):465-71. 25984720 10.1038/nchembio.1816 F1000 Recommendation
18. Thodey K Galanie S Smolke CD: A microbial biomanufacturing platform for natural and semisynthetic opioids. Nat Chem Biol. 2014;10(10):837-44. 25151135 10.1038/nchembio.1613 4167936 F1000 Recommendation
19. Winzer T Kern M King AJ: Plant science. Morphinan biosynthesis in opium poppy requires a P450-oxidoreductase fusion protein. Science. 2015;349(6245):309-12. 26113639 10.1126/science.aab1852 F1000 Recommendation
20. Farrow SC Hagel JM Beaudoin GA: Stereochemical inversion of (S)-reticuline by a cytochrome P450 fusion in opium poppy. Nat Chem Biol. 2015;11(9):728-32. 26147354 10.1038/nchembio.1879 F1000 Recommendation
21. Meziane-Cherif D Courvalin P: Antibiotic resistance: to the rescue of old drugs. Nature. 2014;510(7506):477-8. 24965645 10.1038/510477a
22. Kittendorf JD Sherman DH: Developing tools for engineering hybrid polyketide synthetic pathways. Curr Opin Biotechnol. 2006;17(6):597-605. 17046237 10.1016/j.copbio.2006.09.005
23. Menzella HG Reeves CD: Combinatorial biosynthesis for drug development. Curr Opin Microbiol. 2007;10(3):238-45. 17553731 10.1016/j.mib.2007.05.005
24. Hertweck C: Decoding and reprogramming complex polyketide assembly lines: prospects for synthetic biology. Trends Biochem Sci. 2015;40(4):189-99. 25757401 10.1016/j.tibs.2015.02.001
25. Menzella HG Carney JR Santi DV: Rational design and assembly of synthetic trimodular polyketide synthases. Chem Biol. 2007;14(2):143-51. 17317568 10.1016/j.chembiol.2006.12.002 F1000 Recommendation
26. Bonnett SA Whicher JR Papireddy K: Structural and stereochemical analysis of a modular polyketide synthase ketoreductase domain required for the generation of a cis-alkene. Chem Biol. 2013;20(6):772-83. 23790488 10.1016/j.chembiol.2013.04.014 3875705 F1000 Recommendation
27. Zheng J Gay DC Demeler B: Divergence of multimodular polyketide synthases revealed by a didomain structure. Nat Chem Biol. 2012;8(7):615-21. 22634636 10.1038/nchembio.964 3477503 F1000 Recommendation
28. Zheng J Keatinge-Clay AT: Structural and functional analysis of C2-type ketoreductases from modular polyketide synthases. J Mol Biol. 2011;410(1):105-17. 21570406 10.1016/j.jmb.2011.04.065 F1000 Recommendation
29. Gehret JJ Gu L Gerwick WH: Terminal alkene formation by the thioesterase of curacin A biosynthesis: Structure of a decarboxylating thioesterase. J Biol Chem. 2011;286(16):14445-54. 21357626 10.1074/jbc.M110.214635 3077644 F1000 Recommendation
30. Scaglione JB Akey DL Sullivan R: Biochemical and structural characterization of the tautomycetin thioesterase: Analysis of a stereoselective polyketide hydrolase. Angew Chem Int Ed Engl. 2010;49(33):5726-30. 20623733 10.1002/anie.201000032 3033191 F1000 Recommendation
31. Buchholz TJ Geders TW Bartley FE 3rd: Structural basis for binding specificity between subclasses of modular polyketide synthase docking domains. ACS Chem Biol. 2009;4(1):41-52. 19146481 10.1021/cb8002607 2853223 F1000 Recommendation
32. Tang Y Chen AY Kim CY: Structural and mechanistic analysis of protein interactions in module 3 of the 6-deoxyerythronolide B synthase. Chem Biol. 2007;14(8):931-43. 17719492 10.1016/j.chembiol.2007.07.012 1986752
33. Keatinge-Clay AT: A tylosin ketoreductase reveals how chirality is determined in polyketides. Chem Biol. 2007;14(8):898-908. 17719489 10.1016/j.chembiol.2007.07.009 F1000 Recommendation
34. Tang Y Kim CY Mathews II: The 2.7-Angstrom crystal structure of a 194-kDa homodimeric fragment of the 6-deoxyerythronolide B synthase. Proc Natl Acad Sci U S A. 2006;103(30):11124-9. 16844787 10.1073/pnas.0601924103 1636687 F1000 Recommendation
35. Broadhurst RW Nietlispach D Wheatcroft MP: The structure of docking domains in modular polyketide synthases. Chem Biol. 2003;10(8):723-31. 12954331 10.1016/S1074-5521(03)00156-X F1000 Recommendation
36. Tsai SC Miercke LJ Krucinski J: Crystal structure of the macrocycle-forming thioesterase domain of the erythromycin polyketide synthase: versatility from a unique substrate channel. Proc Natl Acad Sci U S A. 2001;98(26):14808-13. 11752428 10.1073/pnas.011399198 64940 F1000 Recommendation
37. Maier T Leibundgut M Ban N: The crystal structure of a mammalian fatty acid synthase. Science. 2008;321(5894):1315-22. 18772430 10.1126/science.1161269 F1000 Recommendation
38. Smith S Tsai SC: The type I fatty acid and polyketide synthases: A tale of two megasynthases. Nat Prod Rep. 2007;24(5):1041-72. 17898897 10.1039/B603600G 2263081
39. Whicher JR Dutta S Hansen DA: Structural rearrangements of a polyketide synthase module during its catalytic cycle. Nature. 2014;510(7506):560-4. 24965656 10.1038/nature13409 4074775 F1000 Recommendation
40. Dutta S Whicher JR Hansen DA: Structure of a modular polyketide synthase. Nature. 2014;510(7506):512-7. 24965652 10.1038/nature13423 4278352 F1000 Recommendation
41. Smith JL Skiniotis G Sherman DH: Architecture of the polyketide synthase module: surprises from electron cryo-microscopy. Curr Opin Struct Biol. 2015;31:9-19. 25791608 10.1016/j.sbi.2015.02.014
42. Haslinger K Peschke M Brieke C: X-domain of peptide synthetases recruits oxygenases crucial for glycopeptide biosynthesis. Nature. 2015;521(7550):105-9. 25686610 10.1038/nature14141 F1000 Recommendation
43. Hamed RB Gomez-Castellanos JR Henry L: The enzymes of β-lactam biosynthesis. Nat Prod Rep. 2013;30(1):21-107. 23135477 10.1039/c2np20065a
44. Coulthurst SJ Barnard AM Salmond GP: Regulation and biosynthesis of carbapenem antibiotics in bacteria. Nat Rev Microbiol. 2005;3(4):295-306. 15759042 10.1038/nrmicro1128
45. Chang WC Guo Y Wang C: Mechanism of the C5 stereoinversion reaction in the biosynthesis of carbapenem antibiotics. Science. 2014;343(6175):1140-4. 24604200 10.1126/science.1248000 4160820 F1000 Recommendation
46. Sasaki E Ogasawara Y Liu HW: A biosynthetic pathway for BE-7585A, a 2-thiosugar-containing angucycline-type natural product. J Am Chem Soc. 2010;132(21):7405-17. 20443562 10.1021/ja1014037 2881590 F1000 Recommendation
47. Sasaki E Zhang X Sun HG: Co-opting sulphur-carrier proteins from primary metabolic pathways for 2-thiosugar biosynthesis. Nature. 2014;510(7505):427-31. 24814342 10.1038/nature13256 4082789 F1000 Recommendation
48. Peschke U Schmidt H Zhang HZ: Molecular characterization of the lincomycin-production gene cluster of Streptomyces lincolnensis 78-11. Mol Microbiol. 1995;16(6):1137-56. 8577249 10.1111/j.1365-2958.1995.tb02338.x
49. Jothivasan VK Hamilton CJ: Mycothiol: synthesis, biosynthesis and biological functions of the major low molecular weight thiol in actinomycetes. Nat Prod Rep. 2008;25(6):1091-117. 19030604 10.1039/b616489g
50. Cheah IK Halliwell B: Ergothioneine antioxidant potential, physiological function and role in disease. Biochim Biophys Acta. 2012;1822(5):784-93. 22001064 10.1016/j.bbadis.2011.09.017
51. Zhao Q Wang M Xu D: Metabolic coupling of two small-molecule thiols programs the biosynthesis of lincomycin A. Nature. 2015;518(7537):115-9. 25607359 10.1038/nature14137 F1000 Recommendation
52. Melançon CE 3rd: Biochemistry: Elusive source of sulfur unravelled. Nature. 2015;518(7537):45-6. 25607363 10.1038/nature14197
53. Lau W Sattely ES: Six enzymes from mayapple that complete the biosynthetic pathway to the etoposide aglycone. Science. 2015;349(6253):1224-8. 26359402 10.1126/science.aac7202 F1000 Recommendation
54. Canel C Moraes RM Dayan FE: Podophyllotoxin. Phytochemistry. 2000;54(2):115-20. 10872202 10.1016/S0031-9422(00)00094-7