ACS Catalysis
Page 6 of 9
Wright, A.; Koehn, F. Dragmacidin,
bio(indole) alkaloid from a deep water marine sponge. J.
Org. Chem. 1988, 53, 3116–3118.
Enomoto, Y.; Shiomi, K.; Hayashi, M.; Masuma, R.;
Kawakubo, T.; Tomosawa, K.; Iwai, Y.; Omura, S. Herquline
a
new cytotoxic
Dihydroisoquinolines. Org. Lett. 2017, 19, 3151–3154.
Scheller, P. N.; Nestl, B. M. The biochemical
characterization of three imine-reducing enzymes from
Streptosporangium roseum DSM43021, Streptomyces
turgidiscabies and Paenibacillus elgii. Appl. Microbiol.
Biotechnol. 2016, 100, 1–12.
(31)
1
2
3
4
5
(18)
(19)
B,
a New Platelet Aggregation Inhibitor Produced by
Penicillium Herquei Fg-372. J. Antibiot. 1996, 49, 50–53.
Fujita, T.; Hayashi, H. New Brasiliamide Congeners,
Brasiliamides C, D and E, from Penicillium brasilianum
Batista JV-379. Biosci. Biotechnol. Biochem. 2004, 68, 820–
826.
Gu, B.; He, S.; Yan, X.; Zhang, L. Tentative biosynthetic
pathways of some microbial diketopiperazines. Appl.
Microbiol. Biotechnol. 2013, 97, 8439–8453.
(32)
(33)
(34)
(35)
Wetzl, D.; Berrera, M.; Sandon, N.; Fishlock, D.; Ebeling,
M.; Müller, M.; Hanlon, S.; Wirz, B.; Iding, H. Expanding
the Imine Reductase Toolbox by Exploring the Bacterial
Protein-Sequence Space. ChemBioChem 2015, 16, 1749–1756.
Scheller, P. N.; Lenz, M.; Hammer, S. C.; Hauer, B.; Nestl, B.
M. Imine Reductase-Catalyzed Intermolecular Reductive
Amination of Aldehydes and Ketones. ChemCatChem 2015,
7, 3239–3242.
6
7
8
9
(20)
(21)
(22)
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Mhaske, S. B.; Argade, N. P. The chemistry of recently
isolated naturally occurring quinazolinone alkaloids.
Tetrahedron 2006, 62, 9787–9826.
Aleku, G. A.; France, S. P.; Man, H.; Mangas-Sanchez, J.;
Montgomery, S. L.; Sharma, M.; Leipold, F.; Hussain, S.;
Grogan, G.; Turner, N. J.
A reductive aminase from
Mitsukura, K.; Suzuki, M.; Tada, K.; Yoshida, T.; Nagasawa,
T. Asymmetric synthesis of chiral cyclic amine from cyclic
imine by bacterial whole-cell catalyst of enantioselective
imine reductase. Org. Biomol. Chem. 2010, 8, 4533–4535.
Mitsukura, K.; Suzuki, M.; Shinoda, S.; Kuramoto, T.;
Yoshida, T.; Nagasawa, T. Purification and characterization
of a novel (R)-imine reductase from Streptomyces sp.
GF3587. Biosci. Biotechnol. Biochem. 2011, 75, 1778–1782.
.Grogan, G.; Turner, N. J. InspIRED by Nature: NADPH-
Dependent Imine Reductases (IREDs) as Catalysts for the
Preparation of Chiral Amines. Chem. - A Eur. J. 2016, 22,
1900–1907.
Mangas-Sanchez, J.; France, S. P.; Montgomery, S. L.; Aleku,
G. A.; Man, H.; Sharma, M.; Ramsden, J. I.; Grogan, G.;
Turner, N. J. Imine reductases (IREDs). Curr. Opin. Chem.
Biol. 2017, 37, 19–25.
Schrittwieser, J. H.; Velikogne, S.; Kroutil, W. Biocatalytic
Imine Reduction and Reductive Amination of Ketones. Adv.
Synth. Catal. 2015, 357, 1655–1685.
Aspergillus oryzae. Nat. Chem. 2017, 9, 961–969.
Roiban, G.-D., Kern, M., Liu, Z., Hyslop, J., Tey, P. L.,
Levine, M. S., Jordan, L. S., Brown, K. K., Hadi, T., Ihnken,
L. A. F., Brown, M. J. B. Efficient Biocatalytic Reductive
Aminations by Extending the Imine Reductase Toolbox.
ChemCatChem 2017, 9, 4475-4479.
Matzel, P.; Gand, M.; Höhne, M. One-step asymmetric
synthesis of (R)- and (S)-rasagiline by reductive amination
applying imine reductases. Green Chem. 2017, 43, 788–824.
Matzel, P.; Krautschick, L.; Höhne, M. Photometric
Characterization of the Reductive Amination Scope of the
Imine Reductases from Streptomyces tsukubaensis and
Streptomyces ipomoeae. ChemBioChem 2017, 18, 2022–2027.
Huber, T.; Schneider, L.; Präg, A.; Gerhardt, S.; Einsle, O.;
Müller, M. Direct reductive amination of ketones: Structure
and Activity of S-Selective Imine Reductases from
Streptomyces. ChemCatChem 2014, 6, 2248–2252.
(23)
(24)
(25)
(36)
(37)
(38)
(26)
(27)
(28)
(39)
(40)
Borlinghaus, N.; Nestl, B. M. Switching the Cofactor
Specificity of an Imine Reductase. ChemCatChem 2018, 10,
183-187.
Lenz, M.; Borlinghaus, N.; Weinmann, L.; Nestl, B. M.
Recent advances in imine reductase-catalyzed reactions.
World J. Microbiol. Biotechnol. 2017, 33, 199.
Edwards, J. M.; Weiss, U.; Gilardi, R. D.; Karle, I. L.
Formation of
a
heterocyclic cage compound from
Aleku, G. A.; Man, H.; France, S. P.; Leipold, F.; Hussain, S.;
Toca-Gonzalez, L.; Marchington, R.; Hart, S.; Turkenburg, J.
P.; Grogan, G.; Turner, N. J. Stereoselectivity and Structural
Characterisation of an Imine Reductase (IRED) from
Amycolatopsis orientalis. ACS Catal. 2016, 6, 3880–3889.
France, S. P.; Hussain, S.; Hill, A. M.; Hepworth, L. J.;
Howard, R. M.; Mulholland, K. R.; Flitsch, S. L.; Turner, N.
J. 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. 2016, 6, 3753–
3759.
ethylenediamine and glyoxal. Chem. Commun. 1968, 0,
1649–1650.
Takahashi, K. The Reactions of Phenylglyoxal and Related
Reagents with Amino Acids. J. Biochem. 1977, 81, 395–402.
(41)
(29)
(30)
Li, H.; Tian, P.; Xu, J.-H.; Zheng, G.-W. Identification of an
Imine Reductase for Asymmetric Reduction of Bulky
ACS Paragon Plus Environment