Catalysis Science & Technology
Please do not adjust margins
Page 12 of 14
Journal Name
ARTICLE
compounds with ketone and ester moieties would be valuable
to expand their substrate range. Lactones and lactams, e.g. ε-
caprolactone, ε-caprolactam, pentadecanolide and 16-
hexadecanolide, which have received attention because of
their chemical versatility, could be investigated with these
monooxygenase enzymes. Protein engineering of both enzymes
could be a useful approach to improve the binding affinity and
selectivity further for efficient late stage functionalisation of
alkane derived natural products.
2_12, pp. 319-339.
DOI: 10.1039/D0CY01040E
16.
17.
18.
S. G. Bell, R. Zhou, W. Yang, A. B. Tan, A. S. Gentleman, L. L.
Wong and W. Zhou, Chemistry, 2012, 18, 16677-16688.
T. Coleman, S. H. Wong, M. N. Podgorski, J. B. Bruning, J. J.
De Voss and S. G. Bell, ACS Catal., 2018, 8, 5915-5927.
M. N. Podgorski, T. Coleman, R. R. Chao, J. J. De Voss, J. B.
Bruning and S. G. Bell, J. Inorg. Biochem., 2020, 203,
110913.
Q. Cheng, S. Thomas and P. Rouviere, Appl. Microbiol.
Biotechnol., 2002, 58, 704-711.
P. Morgan and R. J. Watkinson, in Biochemistry of microbial
degradation, ed. C. Ratledge, Springer Netherlands,
Dordrecht, 1994, DOI: 10.1007/978-94-011-1687-9_1, pp.
1-31.
19.
20.
Conflicts of interest
“There are no conflicts to declare”.
21.
22.
K. Kostichka, S. M. Thomas, K. J. Gibson, V. Nagarajan and
Q. Cheng, J. Bacteriol., 2001, 183, 6478-6486.
H. Iwaki, S. Wang, S. Grosse, H. Bergeron, A. Nagahashi, J.
Lertvorachon, J. Yang, Y. Konishi, Y. Hasegawa and P. C. Lau,
Appl. Environ. Microbiol., 2006, 72, 2707-2720.
A. E. Shilov and G. B. Shul'pin, Chem. Rev., 1997, 97, 2879-
2932.
F. Kakiuchi and S. Murai, in Activation of Unreactive Bonds
and Organic Synthesis, Springer, 1999, pp. 47-79.
C. Jia, T. Kitamura and Y. Fujiwara, Acc. Chem. Res., 2001,
34, 633-639.
Acknowledgements
We thank the University of Adelaide for financial support.
Md.R.S. thanks the University of Adelaide for an International
PhD scholarship.
23.
24.
25.
26.
27.
Notes and references
a
Current address; Department of Pharmaceutical Technology,
University of Dhaka, Dhaka, Bangladesh.
J. Long, H. Liu, S. Wu, S. Liao and Y. Li, ACS Catal., 2013, 3,
647-654.
A. D. Aloise, M. E. Layton and M. D. Shair, J. Am. Chem. Soc.,
2000, 122, 12610-12611.
1.
J. Fredrickson, F. Brockman, D. Workman, S. Li and T.
Stevens, Appl. Environ. Microbiol., 1991, 57, 796-803.
J. Fredrickson, D. Balkwill, G. Drake, M. Romine, D.
2.
Ringelberg and D. White, Appl. Environ. Microbiol., 1995, 28.
61, 1917-1922.
T. Newhouse and P. S. Baran, Angew. Chem. Int. Ed. , 2011,
50, 3362-3374.
3.
4.
S. G. Bell and L. L. Wong, Biochem. Biophys. Res. Commun., 29.
2007, 360, 666-672.
W. Yang, S. G. Bell, H. Wang, W. Zhou, N. Hoskins, A. Dale, 30.
M. Bartlam, L. L. Wong and Z. Rao, J. Biol. Chem., 2010, 285, 31.
27372-27384.
T. Seiser, O. A. Roth and N. Cramer, Angew. Chem., 2009,
121, 6438-6441.
M. S. Chen and M. C. White, Science, 2007, 318, 783-787.
M. C. White and J. Zhao, J. Am. Chem. Soc., 2018, 140,
13988-14009.
5.
S. G. Bell, W. Yang, J. A. Yorke, W. Zhou, H. Wang, J. Harmer, 32.
R. Copley, A. Zhang, R. Zhou, M. Bartlam, Z. Rao and L. L.
R. Curci, L. D'Accolti and C. Fusco, Acc. Chem. Res., 2006,
39, 1-9.
Wong, Acta Crystallogr. D, 2012, 68, 277-291.
S. G. Bell, A. Dale, N. H. Rees and L. L. Wong, Appl.
Microbiol. Biotechnol., 2010, 86, 163-175.
M. H. Gelb, D. C. Heimbrook, P. Malkonen and S. G. Sligar, 34.
Biochemistry, 1982, 21, 370-377.
I. C. Gunsalus and G. C. Wagner, Methods Enzymol., 1978, 35.
52, 166-188.
E. A. Hall and S. G. Bell, RSC Adv., 2015, 5, 5762-5773.
E. A. Hall, M. R. Sarkar, J. H. Z. Lee, S. D. Munday and S. G. 36.
Bell, ACS Catal., 2016, 6, 6306-6317.
M. Ma, S. G. Bell, W. Yang, Y. Hao, N. H. Rees, M. Bartlam,
W. Zhou, L. L. Wong and Z. Rao, ChemBioChem, 2011, 12, 37.
88-99.
M. T. Fisher and S. G. Sligar, J. Am. Chem. Soc., 1985, 107,
5018-5019.
S. G. Sligar and I. C. Gunsalus, Proc. Natl. Acad. Sci. U. S. A.,
1976, 73, 1078-1082.
M. R. Sarkar, S. Dasgupta, S. M. Pyke and S. G. Bell, Chem.
Commun., 2019, 55, 5029-5032.
33.
K. I. Goldberg and A. S. Goldman, Activation and
functionalization of C-H bonds, American Chemical Society
Washington, DC, 2004.
P. J. Figiel, A. M. Kirillov, M. F. C. G. da Silva, J. Lasri and A.
J. Pombeiro, Dalton Trans., 2010, 39, 9879-9888.
P. J. Figiel, A. M. Kirillov, Y. Y. Karabach, M. N. Kopylovich
and A. J. Pombeiro, J. Mol. Catal. A: Chemical, 2009, 305,
178-182.
M. V. Kirillova, Y. N. Kozlov, L. S. Shul’pina, O. Y. Lyakin, A.
M. Kirillov, E. P. Talsi, A. J. Pombeiro and G. B. Shul’pin, J.
Catal., 2009, 268, 26-38.
M. V. Kirillova, A. M. Kirillov, M. L. Kuznetsov, J. A. Silva, J.
J. F. da Silva and A. J. Pombeiro, Chem. Commun., 2009,
2353-2355.
A. M. Kirillov, M. V. Kirillova, L. S. Shul’pina, P. J. Figiel, K. R.
Gruenwald, M. F. C. G. da Silva, M. Haukka, A. J. Pombeiro
and G. B. Shul’pin, J. Mol. Catal. A: Chemical, 2011, 350, 26-
34.
K. Kamata, K. Yonehara, Y. Nakagawa, K. Uehara and N.
Mizuno, Nat. Chem., 2010, 2, 478.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
38.
39.
J. E. Stok, K. E. Slessor, A. J. Farlow, D. B. Hawkes and J. J.
De Voss, in Monooxygenase, Peroxidase and Peroxygenase 40.
Properties and Mechanisms of Cytochrome P450, eds. E. G. 41.
Hrycay and S. M. Bandiera, Springer International
R. G. Bergman, Nature, 2007, 446, 391.
U. Schuchardt, W. A. Carvalho and E. V. Spinacé, Synlett,
1993, 1993, 713-718.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 12
Please do not adjust margins