Stereoselective Production of Dimethyl-Substituted Carbapenams via Engineered Carbapenem Biosynthesis Enzymes

ACS Catalysis

Volumn 7, Issue 2, 2017, Pages 1279-1285

  Hamed, Refaat B ^a,b   Henry, Luc ^a   Claridge, Timothy D W ^a   Schofield, Christopher J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b Assiut University   (Egypt)

Author keywords

antibiotic biosynthesis; crotonases; protein engineering; stereoselective biocatalysis; lactams

Indexed keywords

AMIDES; BIOCATALYSTS; BIOCHEMISTRY; BIOSYNTHESIS; CATALYSIS; STEREOSELECTIVITY;

ANTIBIOTIC BIOSYNTHESIS; BIOCATALYSIS; CROTONASES; FUNCTIONALIZED; HYDROLYTIC STABILITY; PROTEIN ENGINEERING; QUATERNARY CENTERS; STEREO-SELECTIVE;

ENZYMES;

EID: 85026733864     PISSN: None     EISSN: 21555435     Source Type: Journal    
DOI: 10.1021/acscatal.6b02509     Document Type: Article

References (44)

1. Butler, M. S.; Blaskovich, M. A.; Cooper, M. A. J. Antibiot. 2013, 66, 571-591 10.1038/ja.2013.86
2. Hamed, R. B.; Gomez-Castellanos, J. R.; Henry, L.; Ducho, C.; McDonough, M. A.; Schofield, C. J. Nat. Prod. Rep. 2013, 30, 21-107 10.1039/C2NP20065A
3. Shih, D. H.; Baker, F.; Cama, L.; Christensen, B. G. Heterocycles 1984, 21, 29-40 10.3987/S-1984-01-0029
4. Shih, D. H.; Cama, L.; Christensen, B. G. Tetrahedron Lett. 1985, 26, 587-590 10.1016/S0040-4039(00)89154-6
5. Dürckheimer, W.; Blumbach, J.; Lattrell, R.; Scheunemann, K. H. Angew. Chem., Int. Ed. Engl. 1985, 24, 180-202 10.1002/anie.198501801
6. Hamilton-Miller, J. J. Antimicrob. Chemother. 1999, 44, 729-734 10.1093/jac/44.6.729
7. Earl, J.; Kirkpatrick, P. Nat. Rev. Drug Discovery 2003, 2, 97-98 10.1038/nrd1015
8. Rothstein, J.; Patel, S.; Regan, M.; Haenggeli, C.; Huang, Y.; Bergles, D.; Jin, L.; Hoberg, M.; Vidensky, S.; Chung, D. Nature 2005, 433, 73-77 10.1038/nature03180
9. Panday, S. K. Tetrahedron: Asymmetry 2011, 22, 1817-1847 10.1016/j.tetasy.2011.09.013
10. List, B. Tetrahedron 2002, 58, 5573-5590 10.1016/S0040-4020(02)00516-1
11. Li, R. F.; Stapon, A.; Blanchfield, J. T.; Townsend, C. A. J. Am. Chem. Soc. 2000, 122, 9296-9297 10.1021/ja001723l
12. McGowan, S. J.; Sebaihia, M.; O'Leary, S.; Hardie, K. R.; Williams, P.; Stewart, G. S. A. B.; Bycroft, B. W.; Salmond, G. P. C. Mol. Microbiol. 1997, 26, 545-556 10.1046/j.1365-2958.1997.6001974.x
13. Nunez, L. E.; Mendez, C.; Brana, A. F.; Blanco, G.; Salas, J. A. Chem. Biol. 2003, 10, 301-311 10.1016/S1074-5521(03)00069-3
14. Hamed, R. B.; Batchelar, E. T.; Clifton, I. J.; Schofield, C. J. Cell. Mol. Life Sci. 2008, 65, 2507-2527 10.1007/s00018-008-8082-6
15. Batchelar, E. T.; Hamed, R. B.; Ducho, C.; Claridge, T. D. W.; Edelmann, M. J.; Kessler, B.; Schofield, C. J. Angew. Chem., Int. Ed. 2008, 47, 9322-5 10.1002/anie.200803906
16. Gerratana, B.; Arnett, S. O.; Stapon, A.; Townsend, C. A. Biochemistry 2004, 43, 15936-15945 10.1021/bi0483662
17. Sleeman, M. C.; Schofield, C. J. J. Biol. Chem. 2004, 279, 6730-6736 10.1074/jbc.M311824200
18. Sleeman, M. C.; Sorensen, J. L.; Batchelar, E. T.; McDonough, M. A.; Schofield, C. J. J. Biol. Chem. 2005, 280, 34956-34965 10.1074/jbc.M507196200
19. Hamed, R. B.; Batchelar, E. T.; Mecinovic, J.; Claridge, T. D. W.; Schofield, C. J. ChemBioChem 2009, 10, 246-250 10.1002/cbic.200800652
20. Bodner, M. J.; Li, R.; Phelan, R. M.; Freeman, M. F.; Moshos, K. A.; Lloyd, E. P.; Townsend, C. A. ChemBioChem 2011, 12, 2159-65 10.1002/cbic.201100366
21. Gerratana, B.; Stapon, A.; Townsend, C. A. Biochemistry 2003, 42, 7836-7847 10.1021/bi034361d
22. Clifton, I. J.; Doan, L. X.; Sleeman, M. C.; Topf, M.; Suzuki, H.; Wilmouth, R. C.; Schofield, C. J. J. Biol. Chem. 2003, 278, 20843-20850 10.1074/jbc.M213054200
23. Chang, W. C.; Guo, Y.; Wang, C.; Butch, S. E.; Rosenzweig, A. C.; Boal, A. K.; Krebs, C.; Bollinger, J. M., Jr. Science 2014, 343, 1140-4 10.1126/science.1248000
24. Hamed, R. B.; Henry, L.; Gomez-Castellanos, J. R.; Asghar, A.; Brem, J.; Claridge, T. D. W.; Schofield, C. J. Org. Biomol. Chem. 2013, 11, 8191 10.1039/c3ob41525b
25. Hamed, R. B.; Henry, L.; Gomez-Castellanos, J. R.; Mecinović, J.; Ducho, C.; Sorensen, J. L.; Claridge, T. D. W.; Schofield, C. J. J. Am. Chem. Soc. 2012, 134, 471-479 10.1021/ja208318d
26. Hamed, R. B.; Gomez-Castellanos, J. R.; Thalhammer, A.; Harding, D.; Ducho, C.; Claridge, T. D. W.; Schofield, C. J. Nat. Chem. 2011, 3, 365-71 10.1038/nchem.1011
27. Hamed, R. B.; Gomez-Castellanos, J. R.; Sean Froese, D.; Krysztofinska, E.; Yue, W. W.; Schofield, C. J. ChemBioChem 2016, 17, 471-3 10.1002/cbic.201500644
28. Hamed, R. B.; Mecinovic, J.; Ducho, C.; Claridge, T. D. W.; Schofield, C. J. Chem. Commun. 2010, 46, 1413-1415 10.1039/b924519g
29. Sorensen, J. L.; Sleeman, M. C.; Schofield, C. J. Chem. Commun. 2005, 1155-1157 10.1039/B416423G
30. Erb, T. J.; Berg, I. A.; Brecht, V.; Muller, M.; Fuchs, G.; Alber, B. E. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 10631-10636 10.1073/pnas.0702791104
31. Repka, L. M.; Reisman, S. E. J. Org. Chem. 2013, 78, 12314-12320 10.1021/jo4017953
32. Miller, M. T.; Gerratana, B.; Stapon, A.; Townsend, C. A.; Rosenzweig, A. C. J. Biol. Chem. 2003, 278, 40996-41002 10.1074/jbc.M307901200
33. Miller, M. T.; Bachmann, B. O.; Townsend, C. A.; Rosenzweig, A. C. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 14752-14757 10.1073/pnas.232361199
34. Raber, M. L.; Castillo, A.; Greer, A.; Townsend, C. A. ChemBioChem 2009, 10, 2904-2912 10.1002/cbic.200900389
35. Raber, M. L.; Arnett, S. O.; Townsend, C. A. Biochemistry 2009, 48, 4959-4971 10.1021/bi900432n
36. Albers-Schönberg, G.; Arison, B. H.; Hensens, O. D.; Hirshfield, J.; Hoogsteen, K.; Kaczka, E. A.; Rhodes, R. E.; Kahan, J. S.; Kahan, F. M.; Ratcliffe, R. W.; Walton, E.; Ruswinkle, L. J.; Morin, R. B.; Christensen, B. G. J. Am. Chem. Soc. 1978, 100, 6491-6499 10.1021/ja00488a038
37. Parker, W. L.; Rathnum, M. L. J. Antibiot. 1982, 35, 300-5 10.7164/antibiotics.35.300
38. Haneishi, T.; Nakajima, M.; Serizawa, N.; Inukai, M.; Takiguchi, Y.; Arai, M.; Satoh, S.; Kuwano, H.; Tamura, C. J. Antibiot. 1983, 36, 1581-4 10.7164/antibiotics.36.1581
39. Yoshioka, T.; Watanabe, A.; Kojima, I.; Shimauchi, Y.; Okabe, M.; Fukagawa, Y.; Ishikura, T. J. Antibiot. 1984, 37, 211-7 10.7164/antibiotics.37.211
40. Bycroft, B. W.; Maslen, C.; Box, S. J.; Brown, A. G.; Tyler, J. W. J. Chem. Soc., Chem. Commun. 1987, 1623-1625 10.1039/c39870001623
41. Bycroft, B. W.; Maslen, C.; Box, S. J.; Brown, A.; Tyler, J. W. J. Antibiot. 1988, 41, 1231-1242 10.7164/antibiotics.41.1231
42. Behrens, O. K.; Corse, J.; Edwards, J. P.; Garrison, L.; Jones, R. G.; Soper, Q. F.; Van Abeele, F. R.; Whitehead, C. W. J. Biol. Chem. 1948, 175, 771-792
43. Grogan, G.; Graf, J.; Jones, A.; Parsons, S.; Turner, N. J.; Flitsch, S. L. Angew. Chem., Int. Ed. 2001, 40, 1111-1114 10.1002/1521-3773(20010316)40:6<1111::AID-ANIE11110>3.0.CO;2-2
44. Sleeman, M. C.; MacKinnon, C. H.; Hewitson, K. S.; Schofield, C. J. Bioorg. Med. Chem. Lett. 2002, 12, 597-599 10.1016/S0960-894X(01)00806-X