Table 2.
Reported compounds for which the biosynthesis involves either (A) an NMO-induced nitrous acid release or (B) an NMO-catalyzed N-hydroxylation and subsequent condensation reaction to generate (natural) products with complex functional groups
| Compound | Organism | NMO | Additional reaction remarks | References | |
|---|---|---|---|---|---|
| A. NMO-induced nitrous acid release | |||||
| Further relevant enzymes | Coupling partner for HNO2 | ||||
| Cremeomycin | Actinomyces cremeus NRRL3241 | CreE | CreD (lyase) | 3-Amino-2-hydroxy-4-methoxybenzoate | Waldman et al. (2015); Sugai et al. (2016) |
| Fosfazinomycin | Streptomyces sp. NRRL S-149 | FzmM | FzmL | Aspartate | Gao et al. (2014); Huang et al. (2016) |
| Kinamycin | Streptomyces murayamaensis | FzmM | FzmL | Aspartate | Wang et al. (2018) |
| Lomaiviticin | Salinispora sp. | Strop2198 | Kersten et al. (2013) | ||
| Azamerone | Streptomyces sp. CNQ-766 | n.d. | SF2415B1 after C-amination | Amino dihydroquinone intermediate | Winter et al. (2009) |
| Streptozotocin | Streptomyces achromogenes | Unknown | citrulline derivative | Le Goff and Ouazzani (2014) | |
| Triacsins | Streptomyces aureofaciens ATCC31442 | Tri21 (Asp hydroxylase) | Tri16 (lyase) | Hydrazinoacetate derivative | Twigg et al. (2019) |
| Alanosine | Streptomyces alanosinicus DSM 40606 | AlnM | AlnN | (Diaminopropionate bound to AlnI via PCP) | Wang et al. (2020) |
| B. NMO-catalyzedN-hydroxylation and subsequent condensation reactions | |||||
| Substrate | N-OH condensates with | ||||
| Piperazic acid | Actinomycete bacteria | PzbA homologs | Ornithine (ω position) | Itself (α position) | Hu et al. (2019) |
| Kutznerine | Kutzneria sp. 744 | KtzI | Ornithine (ω position) | Itself (α position) | Fujimori et al. (2007) |
| S56-p1 (hydrazinoacetic acid) | Streptomyces sp. SoC090715LN-17 | Spb38 | Lysine | Glycine | Matsuda et al. (2018) |
| Valanymicin | Streptomyces Viridifaciens MG456-hF10 | VlmH | Isobutylamine | Serine | Parry and Li (1997); Tao et al. (2003); Garg et al. (2008); Garg et al. (2009) |
| Pyridazomycin | Streptomyces violaceoniger sp. griseofuscus | Unknown | Ornithine | Oxaloacetate | Bockholt et al. (1994) |
| Triacsins | Streptomyces aureofaciens ATCC31442 | Tri26 | Lysine | Glycine | Twigg et al. (2019) |
| Alanosine | Streptomyces alanosinicus DSM 40606 | AlnG | l-Diaminopropionate bound to AlnI via PCP | NOx | Wang et al. (2020) |