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. Author manuscript; available in PMC: 2016 Oct 11.
Published in final edited form as: Nat Chem Biol. 2016 Apr 11;12(6):419–424. doi: 10.1038/nchembio.2061

Figure 1. Analysis of the fsq gene cluster and metabolite production.

Figure 1

(a) fsq gene cluster and putative assignments of encoded proteins. TF: transcription factor; FAD: FAD-binding domain protein; MT: N-methyltransferase; D-ala: ATP-grasp enzyme (D-alanine ligase); Trs: transporter; NRPS: nonribosomal peptide synthetase (A = adenylation, T = thiolation, R = short-chain dehydrogenase/reductase domain, P: pyridoxal phosphate binding domain); MO: phenol 2-monooxygenase. (b) Section of the dqfCOSY spectra of OE::fsqA and ΔfsqA metabolite extracts used for comparative metabolomics (DANS). (c) Identified fsq-dependent compounds fumisoquin A and B (1 and 2), including stereochemical assignments via NOESY for 1 (see Supplementary Note), as well as structure of fumisoquin C (3), which decomposes to 4 and 5. (d) Biosynthesis of structurally related isoquinoline alkaloids in plants via coclaurine N-methyltransferase (CNMT), N-methylcoclaurine 3′-monooxygenase (CYP80B), 3′-hydroxy-N-methyl-(S)-coclaurine 4′-O-methyltransferase (4′OMT) and berberine bridge enzyme (BBE).