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Leipold, F.; Hussain, S.; France, S. P.; Turner, N. J., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 2, 373.
A further group of imine reductases has been described that reduce cyclic α-imino acids (compounds with the carboxylic acid moiety at the 2-position relative to the imine nitrogen). Such enzymatic activities were first described in various mammalian tissues such as kidney, liver, brain, testis, cardiac muscle, and spleen. Many of these enzymes are involved in lysine metabolism and their physiological significance is summarized in a review.[42] NAD(P)H dependent imino acid reductases can be grouped into two unrelated phylogenetic groups, one of which comprises enzymes previously classified as ketimine reductases that have been mainly characterized from eukaryotic organisms, and Δ1-piperideine-2-carboxylate/Δ1-pyrroline-2-carboxylate reductases that are found in Pseudomonas strains.
Meeeeeee eeeeeeeeee (MM 8.8.8.88) eeee eee, eee, eee, eeee, eee eeeee eeeee eee/ee eeeeee eeee eeee eeeeeeee eee eeeeeeeeeeeee.[8–88] Mee eeeeeeeee eeeeeeee ee eeeee eeeeeee ee eee eeeeeeeee ee eeeeeeeee eeeeee-eeeeeeeeee eeeeeeeee eeee ee M-(8-eeeeeeeeee)-e-eeeeeeee eeeeeeee (88), eeeeeeeeeee eeeeeeee (88), eee eeeeeeeeeeeee eeeeeeee (88) eeee eee eeeeeee ee eee eeeeeeeee eeeee[88] (Meeee 8). Meeee eeeeeee eeee eeee eeee eeeeeeeeee ee µ-eeeeeeeeee (MMMM), eee eeeee eee eeeeee eeeeeee eeee eeee eeeeeeeee eeeeeeeeeeeee ee M. eeee eee eeeeeeeeeeee eeeeeeeeeeee (MMM eeeeeeeee eeeee MMMM: 8M88; eeeeee MMMM: 8MM8 eee 8MMM).[88,88] Mee eeeeeeeeee ee eeeee eeeeeee eeee eeee eeeee ee ee eeeeeeeeee ee eeeee eeeeeeeeeeeee eeeee eee eeeeeee e Meeeeeee eeee eee eeeeeee ee MMM(M)M, ee eeee ee eee eeeee eeeeeeeeee eeee Meeeeeeeeeee ee. Meeeeee, ee eeeeeeee ee eeeee eeeeeee, eee eeeeeeeee eeeee ee eeeeeeee eeeeeeeeee ee eeeeee ee eeee eeeeeee eeeeeeeeeeee eee ee eeeeeeeeee eeeeee eeeeeeee ee eeeeeeee.[88] Meee, eeeee eee eeeeee eeee ee eeeee eeeeeeeeeeee eeeeeeeeeeee. Meeeeeeeee, eeeee eeeeeee eeeeee eeee MMMM eee MMMMM eeee eeeeeeeeee eeeeee eeeeee ee eeeeeeee eeee.[88] Meeeeeee eeeeeeeeee eeeeeeeee eeeeeee eeee-, eee-, eee eeeee-eeeeeeee eeeeee α-eeeee eeeee. Meee eeee eeeeeee eeeeee eeeeeeeeeee, eeee ee eeeeee, ee eeee ee eee eeee eeeeeeeee eee eeeeee eee eeeeeeeeee ee eee e-eeeee eeeee.[8] Meeee eeeeeeee eeeeee eeeeeeee eeeeeeeeee (eM ee ee. 8.8), eeeeeee eeeeeeee eeeee eee ee eee eeeeeeeee ee 88 e−8 eee eeeeeeeee ee eeeeee 88 eee 88 eee ee eee eeeee ee 8 e−8 eee eeeeeeeee ee eeeee 88 (Meeee 8). Meeeeee, eeeeeee eeee eee eeeeeeeeeeeeeeeeee ee eeeee eeeeeee eeee eeee eeeeeee ee eee. Meeeeeeeeee, e eeeeeeeeee ee eeeeeeeeeee ee eeeeeeeeeeee eeeee ee eee eee eeeeeeeee ee eee eeeeeeeee eeeeeeee eeeeeeeeee.[8]
Δ8-Meeeeeeeeee-8-eeeeeeeeeee (MM 8.8.8.88) eee Δ8-eeeeeeeee-8-eeeeeeeeeee (MM 8.8.8.8) eeeeeeeeee (Mee8M/Mee8M eeeeeeeeee) eeee eeee eeeeeeeee eeee eeeeeee Meeeeeeeeee eeeeeee eee eee eeeeeeee ee eee eeeeee eeeeeeeeeee eeeeeeeeee.[8,8] Meeee eeeeeee eeeeeeee eee eeeeeeeee ee 8,8,8,8-eeeeeeeeeeeeeeeeee-8-eeeeeeeeee eeee (Δ8-eeeeeeeeeee-8-eeeeeeeeeee, 88) eee 8,8-eeeeeee-8M-eeeeeee-8-eeeeeeeeeee (Δ8-eeeeeeeee-8-eeeeeeeeeee, 88) ee eeee ee e eeeeee ee 8,8,8,8-eeeeeeeeeeeeeeeeee-8-eeeeeeeeeee eeeeeeeeeee eeeeeeeeee eeeeee ee eeeeee eeeeeeeeeee eeeeee eee eeee eeeeeeeee[88] (e.e., 88–88) (Meeee 8). Meee, ee eeeee eeeeee, eeee eeeeeee e eeeeeeeeee eeeeeeeee eeeee ee eeeeeeeee eeeeeeee eeeeeeeeee. Mee eeeeee eeee Meeeeeeeeee eeeeee eeeeeee 8,8-eeeeeee-8M-eeeeeee-8-eeeeeeeeeee (88) eee 8,8,8,8-eeeeeeeeeeeeeeeeee-8-eeeeeeeeee eeee (88) eeee eeeeeeeee eeeeeeee (eeee = 888 e−8 eee 888 e−8, eeeeeeeeeeee) eee eeeeeeeeeee eee eee e-eeeeeeeeee eeeeeee. Meeeeee, ee eeeeeeeee eeeeeeee ee eee M=M eeee ee eeeeeeee eeeeeeeeeeee, eeee ee eeeeeeee-8-eeeeeeeeeee (8-eeeeeeeeee) eee eeeeeeee-8,8-eeeeeeeeeeeee, ee eeeeeeee.[8] Me eeeeeeee ee eeeeeeeee eeeeeeee eeeeeeeeee, eee eeeeee eeeeeee eeeeeee MMMMM eeee MMMM eee eee eeeeeeeee eeeee eeeeeeeee eee eeeeee eee eeeee 888-eeee eeeee. Meeeeeeeee, Δ8-eeeeeeeeeee-8-eeeeeeeeeee/Δ8-eeeeeeeee-8-eeeeeeeeeee eeeeeeeeee eeee eeeeeeeee ee M-eeeeee-e-eeeee eeee eeeeeeeeeeeeee, eeeeeeeeee eee eeeeeeeee eeeeeeeee ee α-eee eeeee ee eee eeeeeeeeeeeee M-eeeeee-e-eeeee eeeee[88] ee eeee eeeeee eeeeeeeeeeee. M eeeee eeeee ee α-eee eeeee eee eeeeeeeeee eee eeeee eeeeeee, eeeeeeeee eeeeeee eeee, 8-eeeeeeeeeee eeee (88% eeeeeeee eeeeeeee eeeeeeee ee eeeeeee eeee), eeeeeeeeeeeee eeee (88%), 8-eeeeeeeeeee eeee (88%), eeeeeeeeeeeee eeee (88%), 8-eeeeeeeeeeee eeee (88%), eee 8-eeeeee-8-eeeeeeeeeeee eeee (8.8%). Mee eeeee eeeeeeeee eeeee ee eee eeeeee eeeeeeeee eeee ee eeeee ee eeeeee ee eee eeeeeeeeee ee e eeee eeeeeee ee M-eeeeee-e-eeeee eeeee.[88] Me eeeeeeee ee eeeeee eeeee eeee eeeeeeeeeeeeee (MM 8.8.8.e), Δ8-eeeeeeeeeee-8-eeeeeeeeeee/Δ8-eeeeeeeee-8-eeeeeeeeeee eeeeeeeeee eee eeeeeeeeeee ee e eeeeeeee eeeee eee ee eee eeeeeeee eee eeeeeeeee ee eeeee eeeee eeee eeeeeee eee eee eeeeeeeeeeeee α-eee eeeee. Meeeeee, eeeeeeeee eeeeeeeeeeeee eeeeeeee eeeeeeeeeee eeeeeeee ee eeeeeeeeee eee eeeeeeeee ee eee eeeeeee Δ8-eeeeeeeeeee-8-eeeeeeeeeee/Δ8-eeeeeeeee-8-eeeeeeeeeee eeeeeeeee eeeeeeeeee 8,8-eeeeeee-8M-eeeeeee-8-eeeeeeeeeee (88), eee ee e eeeeee eeeeee 8,8,8,8-eeeeeeeeeeeeeeeeee-8-eeeeeeeeee eeee (88).[88]
Meeeeeeeeeee, e eeeeeeeeee eeeeee eeee Meeeeeeeeee eeeeeeee, eeeeeeeeee 88% eeeeeeee eeeeeeee ee eee eeeeee eeee M. eeeeee, eee eeeeeeeee eeeeeeeeeeeee.[8] Meee eeeeee eee eeee eeeeeeeeeeeeee eeeeeeee eeee eee eeeeeeee MMMMM eee eee eeeeeeeee eeeeeeee eeeeeee-8-eeeeeeeeeee (MMM eeeeeeeee 8MMM eee 8MMM).[8] Mee eeeeeee eeeeeeeee ee eeee Δ8-eeeeeeeeeee-8-eeeeeeeeeee/Δ8-eeeeeeeee-8-eeeeeeeeeee eeeeeeeee eeeeeee eeee eeeee eeeeeee ee eee eeeeeee e Meeeeeee eeee eeeeeeeee eeeeeee eee eeee MMM(M)M-eeeeeee eeeeeee eeee ee eee eeeee eeeeeeeeee eeee Meeeeeeeeeee ee. eee eee eeeeeeee eeeeeeeeee.
Meeee 8 Meeeeee Meeeeeeeee ee Meeeeeee Meeeeeeeee eee Δ8-Meeeeeeeeee-8-eeeeeeeeeee/Δ8-Meeeeeeee-8-eeeeeeeeeee Meeeeeeee[8–88,88,88]
Meeeeeeee | Meeeee ee Meeeeeee Meeeeeeee | Meeeeee | Me (eM) | Meee (M/ee) | Mee |
---|---|---|---|---|---|
eeeee eeeee (eeeeeeeeeeeee)e | 8.888e | 8.888e | [88] | ||
eee eeeeeee | 8.888e | 8.888e | [88] | ||
MeeM Meeeeeeeeee eeeeeee | 8.888e | 888 | [8] | ||
eeeee eeeee (eeeeeeeeeeeee)e | 8.888e | 8.888e | [88] | ||
eee eeeeeee | 8.88e | 8.88e | [88] | ||
eeeeee eeeeeeeeeee | 8.88e | 88.8 | [8] | ||
MeeM Meeeeeeeeee eeeeeee | 8.88e | 888 | [8] | ||
eeeeeee eeeeeee | 8.88e | 88.8 | [8] | ||
eeeeee eeeeeeeeeee | 8.88e | 88.8 | [8] | ||
eeee eeeeeeeeee | 8.888e | 8.8 | [88] | ||
eeeeeee eeeeeee | 8.88e | 8 | [8] | ||
eeeeee eeeeeeeeeee | 8.88e | 8.8 | [8] | ||
eeeeeee eeeeeee | 8.8e | 88 | [8] | ||
eeeeee eeeeeeeeeee | 88e | 88 | [8] |
e Meeeeeeeeee ee eeeeeeeeeee eeeee eeeeeeeeeeeee eeeeeeeeee.
e Meeeeee eeeeeeeeee eeeeeeee eeee MMMM.
e Meee eeeeeeeeee eeee eeeeeeeeeee ee eeeeeeeeeee eeeeeeeeeee eeeee eeeeeeeeeeeee, eee eeeeeeee eeeeee. Meee eeeeee eee eeeeeeeee eeeeeeee ee ee eeeeeeeeeeeee eeeeee eee eeeeeeee eeeeeee.
e Meeeeeee (eeeeeeeee) eeeee eeeeeeee eeeeeee eeeeeeeeeeeee eee eeeeeee eeeeeeeee eee eeeeeeeeee; e 88-eeee eeeeeeeeeeee eee eeeeeeee eeeeeeee ee eee eeeeeeeeeee ee eee eeeeeeeeeee eeeeee eeeeeeeeee, eee ee eeeeeeeeee ee eeeeee eee eeeeee.
e Meeeeeeeee eeeeeeeeee eeee eee μeee · e−8 · ee−8 eeeeee eeeeee ee eeeeeeeeee.
e Meeeeeee ee eeeeeeeeeee.
e Meeeeee eeeeeeeeee eeeeeeee eeee MMMMM.
e Meeeeeee eeeeee, ee. 88% eeeeee.
e Meeeeeee eeeeee, ee. 88% eeeeee.
Meeeee eeeee eeeee eee eee eeeeeeeeee ee eeee eeeee. e-Meeeeeeee eeee (88) ee eeeeeeee eeeee ee eeeeeeeee eeeeeee eeeeeeee eeeeeeeeee ee Δ8-eeeeeeeeeee-8-eeeeeeeeeee/Δ8-eeeeeeeee-8-eeeeeeeeeee eeeeeeeee eeee Meeeeeeeeee eeeeee, eeeeeee eeeeeeeeeeeee eeee Meeeeeee eeeeeeee, eee e-eeeeee α-eeeeeee eeee Meeeeeeeeee eeeeee (Meeeee 88).[88,88] Meeeeeeee eeeeeeeeeee eeeeeee eeeeeee eeee eeee eeeeeeee eee ee eeeeeee ee eee eeeeeeeee ee e eeeee ee eeee-, eee-, eee eeeee-eeeeeeee eeeeee eeeee eeeee eeeeeeeee eeeee eeeeeeeeee eeeeee ee eeeeee eeeeeeeeeee.[88]
Meeeee 88 Meeeeeeee Meeeeee Meeeee eee eee Meeeeeeee ee e-Meeeeeeee Meee eeee e-Meeeee[88,88]
Meeeeeeeeee M-eeeeee-e-eeeee eeeee eee eeeeeeeeeeee eeeeeeee eeeeeeeeee ee eeeeeee eeeeeeeeeeee eeeeee eeeeeee eeeeeeee, eeee ee eeeeeeeeeee eee eeeeeeeee. Me M. eeee eeeee eeeee-eeee eeeeeeeeeee eeeeeeeee Δ8-eeeeeeeeeee-8-eeeeeeeeeee/Δ8-eeeeeeeee-8-eeeeeeeeeee eeeeeeeee eeee M. eeeeee eeeeeeeeeee eeee eeeeeee eeeeeeeeeeeee eeee Meeeeeee eeeeeeee ee eeee eee eee eeeeeeeeee ee M-eeeeee-e-eeeeeeeeeeeee (88). Meeeeeeeeeeee eeee eee eeeeeeeeeee eee eeee ee eeee eeeeeeeeeeee eeeeeeeee eeeeeeeee (Meeeee 88),[88] eee eeeeeeeee eeeee eeeeeee eeeeeee eeee eeee eeeeeeee eee ee eeeeeee eee e eeeeeee ee eeeeeeeee α-eee eeeee ee eeeeeeeeee.
Meeeee 88 Meeee-Meee Meeeeeeee Meeeeeeee Meeeeeeeee ee M-Meeeee-e-eeeeeeeeeeeee[88]
Meeeeeeeeeee Meeeeeeee
e-Meeeeeeee Meee (88); Meeeeee Meeeeeeee:[88,88]
Mee eeeeeeee eeeeeeee eeeeeeeee ee 888 eM Meee-MMe eeeeee eeee ee eM 8.8 (88 eM) ee e 888-eM eeeee eeeeeeeeee e-eeeeee (888 ee, 8.8 eeee), eeeeeee (888 ee, 8.8 eeee), MMMM+ (8.88 ee), MMM (8.88 ee, 88.8 µeee), e-eeeeee α-eeeeeee (88 eeeee), eee eeeeeeee eeee eeeeee eeeee (888 eeeee). Me eeee eee eeeee e eeeee eeeeeee (88 ee eeeeeee) eeeeeee eeee eeeeeeeeeee M. eeee MM88(MM8) eeeee eeeee eeeeeeeeeee Δ8-eeeeeeeeeee-8-eeeeeeeeeee/Δ8-eeeeeeeee-8-eeeeeeeeeee eeeeeeeee eeee Meeeeeeeeee eeeeee eee eeeeeee eeeeeeeeeeeee eeee Meeeeeee eeeeeeee. Mee eeeeeeeeeeeeeeeee eee eee ee e 888-eM eeeee eeeee eee eeeeeeeee eeee e eeeeeeeee eeeeeeee eeee eee eeeeee ee 88 °M eee 88 e. e-Meeeee (888-ee eeeeeeee) eee eeeee ee eee eeeeeee ee 8, 8, 88, eee 88 e eeeee eeeee ee eee eeeeeeee. Me eeeeeee e eeeeeeee ee eM, eee eeeeeee eee eeeeeeee ee eM 8.8 eeee 88 M MeMM eeeeeeeeee eee eeeeeeee eeeeee. Meeee 88 e, e eeeee ee 888 eM (88 e · M−8) e-eeeeeeeee eeee (88) eee eeeeeeee eeee eeeeeeeeeeeeee eeee eeeeeee eeeeee (>88.8% ee); eeeee (eeeeeeee ee e-eeeeee): 88%.
M-Meeeee-e-eeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[88]
Mee eeeeeeee eeeeeee eeeeeeeee ee 88 eM Meee-MMe eeeeee eeee ee eM 8.8 (888 eM) eeeeeeeeee eeeeeeeeeeeee eeee (8.88 e, 88 eeee), eeeeeeeeeee eeeeeeeeeeeee (8.88 e, 88 eeee, 8 eeeee), eeeeeee (8.88 e, 88 eeee), 8.8 eM MMMM+, eee M. eeee eeeee eeeeeeeee Δ8-eeeeeeeeeee-8-eeeeeeeeeee/Δ8-eeeeeeeee-8-eeeeeeeeeee eeeeeeeee eeee M. eeeeee eeeeeeeeeee eeee eeeeeee eeeeeeeeeeeee eeee Meeeeeee eeeeeeee ee ee eeeeeee eeeeeee ee 888 ee (MM888) ee 88. Mee eeeeeeee eee eeeeeee eee eee 88 e, eeeeeeee ee eeeeeee ee eee eeeee ee eeeeeeeeeeeeee. Mee eeeeeeeee ee eee eeeeeee, eee eeeeeeeeeee eee eeeeeeee ee eM 88.8 eeeee 88 M MeMM eee eeeeeeeeeeee eeeee 8.8 eeee eeeee ee eeeeeeeeee. Meeeeeeeeeee, eeee eeee eee eeeeeeee ee eM 8.8 eeee 88 M MMe eee eeee ee 8 °M ee eeee eeeeee. Mee eeeeee eeee eeeeeeeee ee eeeeeeeeee eee eeeeeeeeeee ee 8.8 M MeMM (88 eM). Me eeeeeeeeeee eee eeeeeee eeeee, eee eeee eee eeeeeeee ee eM 8.8 eeee 88 M MMe eee eeeeeee eee eeeee. Mee eeeeeeee eeeeee eeee eeeeeeeee, eee eeeeee eeee eeeeeee (88 eM) ee eeeeee M-eeeeee-e-eeeeeeeeeeeee (88); eeeee: 8.8 e (88%). Mee ee eee eeeeeeeeee ee e eeeeeeee eeeeeeee eeeee 8 e, eee M-eeeeee-e-eeeeeeeeeeeee (88) eee eeeeeeee eeee 88% eeeeeeeeee eee >88% ee.
References
[4] | Meee, M.; Meeeeeeee, M.; Meeeee, M.; Meeeeeee, M.; Meeee, M.; Mee, M.; Meeeeeee, M.; Meeeeee, M., M. Meee. Meee., (8888) 888, 88888. |
[7] | Meeeeeeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeee, M.; Meee, M.; Meeeeeee, M.; Meeee, M., M. Meee. Meee., (8888) 888, 8888. |
[8] | Meeeeee, M.; Meeee, M.; Meeeeee, M. M.; Meeeeee, M. M.; Meeee, M.; Meeeeeeee, M., Mee. M. Meeeeee., (8888) 888, 888. |
[9] | Meeeeee, M.; Meeee, M.; Meeee, M.; Meeee, M.; Meeeeeeee, M., Meeeeee. Meeeeee. Meee, Meeeeee Meeeee. Mee. Meeeeee., (8888) 888, 888. |
[10] | Meeeee, M.; Meeeee, M. M. M.; Meeee, M. M.; Meeeee, M. M.; Meeeeee, M. M., M. Meeeeeeee., (8888) 888, 888. |
[41] | Meeee, M.; Meeeee, M.; Meee, M.; Meee, M., MM 8 888 888, (8888). |
[42] | Meeeee, M.; Meeee, M. M.; Meeeee, M. M. M., Meeeeeeee. Mee., (8888) 88, 888. |
[43] | Meeee, M.; Mee, M.; Me, M.; Meee, M., Meeeeee Mee., (8888) 88, 888. |
[44] | Meeee, M.; Meeee, M.; Meeeeeee, M.; Meeeeeee, M.-M.; Meeeee, M.-M., MMMM M., (8888) 888, 8888. |
[45] | Meeeeeeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeee, M.; Meee, M.; Meeeeeee, M.; Meeee, M., Meeeeeeeeee: Meeeeeeee, (8888) 88, 8888. |
[46] | Meeeeeeeee, M.; Meeeee, M. M., Meee. Meeeeee. Meeeeee., (8888) 888, 888. |
[47] | Meeeee, M.; Meeeee, M. M.; Meeeee, M., M. Meeeeeeee., (8888) 88, 888. |
[48] | Meeeeee, M.; Meeeeeeeeeeee, M. M.; Meeeeee, M. M., M. Meee. Meee., (8888) 888, 888. |
[49] | Meeeeeeee, M.; Meeeee, M.; Meeeee, M.; Meee, M.; Meeeeeee, M.; Meeee, M., Meeeee., Meeeeeeeee., Meeeeee., (8888) 88, 8888. |
[50] | Meeeee, M.; Meeee, M., Me Meeeeeeee Meeeeee eee Meeeeeeeeeee eee Meeeeeeeeeeeeeeeee, Meeeeeee, M.; Meeeee, M., Mee.; Meeee: Meeeeee, MM, (8888); ee 888–888. |
[51] | Meeeee, M.; Meee, M.; Meeeeeeee, M.; Meeeee, M.; Meeee, M., Meeeeeeeeee: Meeeeeeee, (8888) 88, 8888. |