3ngc

Structural highlights

Function

HLNO_PAENI Involved in the degradation of L-nicotine (PubMed:5849820). Catalyzes the oxidation of (S)-6-hydroxynicotine (6-hydroxy-L-nicotine) to 6-hydroxypseudooxynicotine (PubMed:5849820, PubMed:4965794, PubMed:5646150, PubMed:21383134, PubMed:26744768, PubMed:28080034). Oxidation of the pyrrolidine ring of (S)-6-hydroxynicotine leads to the formation of the optically inactive 6-hydroxy-N-methylmyosmine, which hydrolyzes spontaneously to 6-hydroxypseudooxynicotine (PubMed:4965794, PubMed:21383134, PubMed:26744768, PubMed:28080034). Acts with absolute stereospecificity on the L-form of 6-hydroxynicotine (PubMed:4965794). Can also use (S)-6-hydroxynornicotine (PubMed:26744768, PubMed:28080034).^{[1] [2] [3] [4] [5] [6]}

References

1. ↑ Kachalova G, Decker K, Holt A, Bartunik HD. Crystallographic snapshots of the complete reaction cycle of nicotine degradation by an amine oxidase of the monoamine oxidase (MAO) family. Proc Natl Acad Sci U S A. 2011 Mar 22;108(12):4800-5. Epub 2011 Mar 7. PMID:21383134 doi:http://dx.doi.org/10.1073/pnas.1016684108
2. ↑ Fitzpatrick PF, Chadegani F, Zhang S, Roberts KM, Hinck CS. Mechanism of the Flavoprotein L-Hydroxynicotine Oxidase: Kinetic Mechanism, Substrate Specificity, Reaction Product, and Roles of Active-Site Residues. Biochemistry. 2016 Feb 2;55(4):697-703. PMID:26744768 doi:10.1021/acs.biochem.5b01325
3. ↑ Fitzpatrick PF, Chadegani F, Zhang S, Dougherty V. Mechanism of Flavoprotein l-6-Hydroxynicotine Oxidase: pH and Solvent Isotope Effects and Identification of Key Active Site Residues. Biochemistry. 2017 Feb 14;56(6):869-875. PMID:28080034 doi:10.1021/acs.biochem.6b01160
4. ↑ Decker K, Dai VD. Mechanism and specifcity of L Eur J Biochem. 1967 Dec;3(2):132-8. PMID:4965794 doi:10.1111/j.1432-1033.1967.tb19507.x
5. ↑ Dai VD, Decker K, Sund H. Purification and properties of L-6-hydroxynicotine oxidase. Eur J Biochem. 1968 Mar;4(1):95-102. PMID:5646150 doi:10.1111/j.1432-1033.1968.tb00177.x
6. ↑ Decker K, Bleeg H. Induction and purification of stereospecific nicotine oxidizing enzymes from Arthrobacter oxidans. Biochim Biophys Acta. 1965 Aug 24;105(2):313-24. PMID:5849820 doi:10.1016/s0926-6593(65)80155-2