Flavin-dependent N-hydroxylating enzymes: distribution and application
Amino groups derived from naturally abundant amino acids or (di)amines can be used as “shuttles” in nature for oxygen transfer to provide intermediates or products comprising N-O functional groups such as N -hydroxy, oxazine, isoxazolidine, nitro, nitrone, oxime, C -, S -, or N -nitroso, and azoxy u...
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Veröffentlicht in: | Applied microbiology and biotechnology 2020-08, Vol.104 (15), p.6481-6499 |
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Sprache: | eng |
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Zusammenfassung: | Amino groups derived from naturally abundant amino acids or (di)amines can be used as “shuttles” in nature for oxygen transfer to provide intermediates or products comprising N-O functional groups such as
N
-hydroxy, oxazine, isoxazolidine, nitro, nitrone, oxime,
C
-,
S
-, or
N
-nitroso, and azoxy units. To this end, molecular oxygen is activated by flavin, heme, or metal cofactor-containing enzymes and transferred to initially obtain
N
-hydroxy compounds, which can be further functionalized. In this review, we focus on flavin-dependent
N
-hydroxylating enzymes, which play a major role in the production of secondary metabolites, such as siderophores or antimicrobial agents. Flavoprotein monooxygenases of higher organisms (among others, in humans) can interact with nitrogen-bearing secondary metabolites or are relevant with respect to detoxification metabolism and are thus of importance to understand potential medical applications. Many enzymes that catalyze
N
-hydroxylation reactions have specific substrate scopes and others are rather relaxed. The subsequent conversion towards various N-O or N-N comprising molecules is also described. Overall, flavin-dependent
N
-hydroxylating enzymes can accept amines, diamines, amino acids, amino sugars, and amino aromatic compounds and thus provide access to versatile families of compounds containing the N-O motif. Natural roles as well as synthetic applications are highlighted.
Key points
• N-O and N-N comprising natural and
(
semi
)
synthetic products are highlighted
.
• Flavin-based NMOs with respect to mechanism
,
structure
,
and phylogeny are reviewed
.
• Applications in natural product formation and synthetic approaches are provided
.
Graphical abstract
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ISSN: | 0175-7598 1432-0614 |
DOI: | 10.1007/s00253-020-10705-w |