Deciphering Piperidine Formation in Polyketide-Derived Indolizidines Reveals a Thioester Reduction, Transamination, and Unusual Imine Reduction Process

ACS Chemical Biology

Volumn 11, Issue 12, 2016, Pages 3278-3283

  Peng, Haidong ^a   Wei, Erman ^a   Wang, Jiali ^a   Zhang, Yanan ^a   Cheng, Lin ^a   Ma, Hongmin ^a   Deng, Zixin ^a   Qu, Xudong ^a,b  

^a WUHAN UNIVERSITY   (China)

^b Institute of Advanced Materials (IAM)   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACYL COENZYME A DEHYDROGENASE; CYCLOPROPANE; IMINE; INDOLIZIDINE DERIVATIVE; OXIDOREDUCTASE; PIPERIDINE; POLYKETIDE; THIOESTER; ACYL CARRIER PROTEIN; PIPERIDINE DERIVATIVE;

ARTICLE; BACTERIAL GENE; BIOSYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; GENE CLUSTER; NONHUMAN; PRIORITY JOURNAL; REDUCTION; TRANSAMINATION; CHEMISTRY; ENZYMOLOGY; METABOLISM; STREPTOMYCES;

ACYL CARRIER PROTEIN; ACYL-COA DEHYDROGENASES; BIOSYNTHETIC PATHWAYS; IMINES; INDOLIZIDINES; PIPERIDINES; POLYKETIDES; STREPTOMYCES;

EID: 85006335468     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/acschembio.6b00875     Document Type: Article

References (28)

1. Dewick, P. M. ( 2009 ) Medicinal Natural Products: A Biosynthetic Approach, Wiley-VCH, Chichester, U.K.
2. Berdy, J. ( 2005 ) Bioactive microbial metabolites J. Antibiot. 58, 1-26 10.1038/ja.2005.1
3. Hesse, M. ( 2002 ) Alkaloids: Nature's Curse or Blessing?, Wiley-VCH, Zurich.
4. O'Hagan, D. ( 2000 ) Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids Nat. Prod. Rep. 17, 435-446 10.1039/a707613d
5. Michael, J. P. ( 2008 ) Indolizidine and quinolizidine alkaloids Nat. Prod. Rep. 25, 139-165 10.1039/B612166G
6. Simon, R. C., Grischek, B., Zepeck, F., Steinreiber, A., Belaj, F., and Kroutil, W. ( 2012 ) Regio and stereoselective monoamination of diketones without protecting groups Angew. Chem., Int. Ed. 51, 6713-6716 10.1002/anie.201202375
7. Schrittwieser, J. H. and Resch, V. ( 2013 ) The role of biocatalysis in the asymmetric synthesis of alkaloids RSC Adv. 3, 17602-17632 10.1039/c3ra42123f
8. He, M. ( 2006 ) Pipecolic acid in microbes: biosynthetic routes and enzymes J. Ind. Microbiol. Biotechnol. 33, 401-407 10.1007/s10295-006-0078-3
9. Herbert, R. B. ( 2001 ) The biosynthesis of plant alkaloids and nitrogenous microbial metabolites Nat. Prod. Rep. 18, 50-65 10.1039/a809393h
10. Wallwey, C., Matuschek, M., Xie, X.-L., and Li, S.-M. ( 2010 ) Ergot alkaloid biosynthesis in Aspergillus fumigatus: Conversion of chanoclavine-I aldehyde to festuclavine by the festuclavine synthase FgaFS in the presence of the old yellow enzyme FgaOx3 Org. Biomol. Chem. 8, 3500-3508 10.1039/c003823g
11. Leipold, F., Hussain, S., Ghislieri, D., and Turner, N. J. ( 2013 ) Asymmetric reduction of cyclic imines catalyzed by a whole-cell biocatalyst containing an (S)-imine reductase ChemCatChem 5, 3505-3508 10.1002/cctc.201300539
12. Hussain, S., Leipold, F., Man, H., Wells, E., France, S. P., Mulholland, K. R., Grogan, G., and Turner, N. J. ( 2015 ) An (R)-imine reductase biocatalyst for the asymmetric reduction of cyclic imines ChemCatChem 7, 579-583 10.1002/cctc.201402797
13. France, S. P., Hussain, S., Hill, A. M., Hepworth, L. J., Howard, R. M., Mulholland, K. R., Flitsch, S. L., and Turner, N. J. ( 2016 ) One-pot cascade synthesis of mono-and disubstituted piperidines and pyrrolidines using carboxylic acid reductase (CAR), ω-transaminase (ω-TA), and imine reductase (IRED) biocatalysts ACS Catal. 6, 3753-3759 10.1021/acscatal.6b00855
14. Schrittwieser, J. H., Velikogne, S., and Kroutil, W. ( 2015 ) Biocatalytic imine reduction and reductive amination of ketones Adv. Synth. Catal. 357, 1655-1685 10.1002/adsc.201500213
15. Leeper, F. J., Padmanabhan, P., Kirby, G. W., and Sheldrake, G. N. ( 1987 ) Biosynthesis of the indolizidine alkaloid, cyclizidine J. Chem. Soc., Chem. Commun. 505-506 10.1039/c39870000505
16. Ohno, S., Katsuyama, Y., Tajima, Y., Izumikawa, M., Takagi, M., Fujie, M., Satoh, N., Shin-ya, K., and Ohnishi, Y. ( 2015 ) Identification and characterization of the streptazone E biosynthetic gene cluster in Streptomyces sp. MSC090213JE08 ChemBioChem 16, 2385-2391 10.1002/cbic.201500317
17. Huang, W., Kim, S. J., Liu, J., and Zhang, W. ( 2015 ) Identification of the polyketide biosynthetic machinery for the indolizidine alkaloid cyclizidine Org. Lett. 17, 5344-5347 10.1021/acs.orglett.5b02707
18. Gomi, S., Ikeda, D., Nakamura, H., Naganawa, H., Yamashita, F., Hotta, K., Kondo, S., Okami, Y., Umezawa, H., and Iitaka, Y. ( 1984 ) Isolation and structure of a new antibiotic, indolizomycin, produced by a strain SK2-52 obtained by interspecies fusion treatment J. Antibiot. 37, 1491-1494 10.7164/antibiotics.37.1491
19. Gomez-Escribano, J. P., Song, L., Fox, D. J., Yeo, V., Bibb, M. J., and Challis, G. L. ( 2012 ) Structure and biosynthesis of the unusual polyketide alkaloid coelimycin P1, a metabolic product of the cpk gene cluster of Streptomyces coelicolor M145 Chem. Sci. 3, 2716-2720 10.1039/c2sc20410j
20. Ehmann, D. E., Gehring, A. M., and Walsh, C. T. ( 1999 ) Lysine biosynthesis in saccharomyces cerevisiae: mechanism of α-aminoadipate reductase (Lys2) involves posttranslational phosphopantetheinylation by Lys5 Biochemistry 38, 6171-6177 10.1021/bi9829940
21. Barajas, J. F., Phelan, R. M., Schaub, A. J., Kliewer, J. T., Kelly, P. J., Jackson, D. R., Luo, R., Keasling, J. D., and Tsai, S.-C. ( 2015 ) Comprehensive structural and biochemical analysis of the terminal myxalamid reductase domain for the engineered production of primary alcohols Chem. Biol. 22, 1018-1029 10.1016/j.chembiol.2015.06.022
22. Kelley, L. A., Mezulis, S., Yates, C. M., Wass, M. N., and Sternberg, M. J. E. ( 2015 ) The Phyre2 web portal for protein modeling, prediction and analysis Nat. Protoc. 10, 845-858 10.1038/nprot.2015.053
23. Zehner, S., Kotzsch, A., Bister, B., Süssmuth, R. D., Méndez, C., Salas, J. A., and van Pée, K.-H. ( 2005 ) A regioselective tryptophan 5-halogenase is involved in pyrroindomycin biosynthesis in streptomyces rugosporus LL-42D005 Chem. Biol. 12, 445-452 10.1016/j.chembiol.2005.02.005
24. Ghisla, S. and Thorpe, C. ( 2004 ) Acyl-CoA dehydrogenases, a mechanistic overview Eur. J. Biochem. 271, 494-508 10.1046/j.1432-1033.2003.03946.x
25. Runguphan, W., Qu, X., and O'Connor, S. E. ( 2010 ) Integrating carbon-halogen bond formation into medicinal plant metabolism Nature 468, 461-464 10.1038/nature09524
26. Mathew, S. and Yun, H. ( 2012 ) ω-Transaminases for the production of optically pure amines and unnatural amino acids ACS Catal. 2, 993-1001 10.1021/cs300116n
27. Akhtar, M. K., Turner, N. J., and Jones, P. R. ( 2013 ) Carboxylic acid reductase is a versatile enzyme for the conversion of fatty acids into fuels and chemical commodities Proc. Natl. Acad. Sci. U. S. A. 110, 87-92 10.1073/pnas.1216516110
28. Awodi, U. R., Ronan, J. L., Masschelein, J., de los Santos, E. L. C., and Challis, G. L. ( 2016 ) Thioester reduction and aldehyde transamination are universal steps in actinobacterial polyketide alkaloid biosynthesis Chem. Sci. 10.1039/C6SC02803A