Institut für Pharmazeutische Biologie und Biotechnologie, Philipps-Universität. Marburg, Deutschhausstrasse 17A, Marburg, Germany
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1 Electronic Supplementary Material for: Substrate promiscuity of secondary metabolite enzymes: Prenylation of hydroxynaphthalenes by fungal indole prenyltransferases Xia Yu, Xiulan Xie, and Shu-Ming Li * Xia Yu, Shu-Ming Li* Institut für Pharmazeutische Biologie und Biotechnologie, Philipps-Universität Marburg, Deutschhausstrasse A, 0 Marburg, Germany * Correspondence: shuming.li@staff.uni-marburg.de Shu-Ming Li Zentrum für Synthetische Mikrobiologie, Philipps-Universität Marburg, 0 Marburg Xiulan Xie Fachbereich Chemie, Philipps-Universität Marburg, ans-meerwein-strasse, 0 Marburg, Germany
2 Table S: Conversion rates of the five enzymes towards different substrates after incubation for h or h Conversion rate (%) Substrate AnaPT -DMATS CdpNPT CdpCPT SirD h h h h h h h h h h naphthalene (a) naphthol (b) naphthol (c) ,-dihydroxynaphthalene (d) ,-dihydroxynaphthalene (e) ,-dihydroxynaphthalene (f) ,-dihydroxynaphthalene (g) ,-dihydroxynaphthalene (h) ,-dihydroxynaphthalene (i) ,-dihydroxynaphthalene (j) ,-dihydroxy--naphthoic acid (k) ,-dihydroxy--naphthoic acid (l) : not detected, conversion rate 0. %
3 Table S: - and C-NMR data of monoprenylted products in CD OD. Chemical shifts (δ) are given in ppm and coupling constants (J) in z. Compd 0 ' 0 ' 0 ' ' ' ' 0 ' ' ' 0 O ' ' ' 0 ' ' ' ' ' ' b f g i i j Pos. δ C δ, multi., J δ C δ, multi.,j δ C δ, multi.,j δ C δ, multi.,j δ, multi., J δ C δ, multi.,j. \. \. \ 0. \.0, overlaps c. \ 0.., d,. 0.., d,. 0.., d,. 0. \ \. \..0, d,...00, d,.0.., d,...0, overlaps.0, dd,.,. a.., d,.. \. \. \.., d,.., d,. b.., d,...0, d,. 0.., d,..., d,. 0..0, overlaps., d,. c 0.., d,..., ddd,.,.,.. \..0, dd,.,.. \ \.0., dd,.,...0, ddd,.,.,..., dd,.,.. \..0, overlaps.0, dd,.0,. a.0 \.., d,...0, d,.0 0.., d,...0, d,..0, d,. b 0.., d,..0 \. \. \. \ \. \ 0. \. \.0 \. \ \. \ \ \ \ \ \ \ \ \ \ \ \.., d,..., d,..0., d,..., d,..0, overlaps.., d,. '.., br.t,.0.., br.t,..., br.t,.0.., br.t,.., m.., br.t,.. \. \. \. \ \. \ '..0, s.., s.., s.., s., s.., s '.., s.., s.., s.., s., s.., s a, b, c : exchangeable protons Signals were assigned by comparison of the spectra of the enzyme products with those of the substrate, and with each other, as well as by SQC and MBC correlations.
4 Table S (continued) Compd 0 ' ' ' ' ' ' 0 O ' ' ' 0 CO ' ' ' 0 CO ' ' ' 0 CO j j k k l Pos. δ, multi., J δ, multi., J δ C δ, multi.,j δ C δ, multi.,j δ C δ, multi.,j., s.00, overlaps.., s.., s.., s \ \. \. \. \ \., dd,.,.. \. \. \., s., d,. 0.., s 0.., s.., s., d,.., d,.. \. \.., d,.., dd,.,.., dd,.,. 0.., d,.. \.., d,. \ \.., d,...0, d,. 0. \., d,..00, overlaps.0 \.., d,.. \ \ \. \. \. \ 0 \ \. \. \. \ \ \. \. \. \., d,.., d,..., d,.0.., d,..., d,. '.0, m., m.., br.t,..., br.t,..., br.t,. \ \. \. \. \ '., s., s.., s.., s.., s '., s., s.., s.., s.., s Signals were assigned by comparison of the spectra of the enzyme products with those of the substrate, and with each other, as well as by SQC and MBC correlations.
5 Table S: - and C-NMR data of diprenylted products in CD OD. Chemical shifts (δ) are given in ppm and coupling constants (J) in z. Compd ' ' ' 0 ' '' '' ' '' '' '' ' ' '' 0 ' ' ' ' ' ' 0 O ' '' '' '' ' '' '' ' '' ' O ' ' ' 0 ' '' '' ' '' ' ' ' 0 ' '' '' ' '' 0 ' ' ' ' ' ' 0 O ' '' '' ' '' '' '' ' ' O '' ' ' ' 0 ' 0 ' O ' ' '' '' ' '' i i i i j j j j j Pos. δ, multi., J δ, multi., J δ, multi., J δ, multi., J δ, multi., J δ, multi., J δ C δ, multi., J δ C δ, multi., J δ C δ, multi., J \ \ \ \ \., s.0 \. \ 0.., s \ \ \ \ \ \. \. \. \ \.0, d,.0., d,.0.0, d,.., d,. \..0, d,..., d,.. \., s., d,.0., d,.0., d,.., d,.., s.., d,..., d,..., s., d,..0, overlaps., d,.., s., s 0.., d,. 0..0, d,..., d,. \ \ \ \ \ \..0, dd,.,..., dd,.,..., dd,.,..00, dd,.,..0, d,.0.0, overlaps.0, dd,.,. \ \. \. \.0 \., d,.., d,.0., d, 0.0., d,.., s., s 0.., d,. 0.., d,. 0.., d,. \ \ \ \ \ \. \. \.0 \ 0 \ \ \ \ \ \. \.0 \. \., d,.., d,.., d,..0, d,.., d,.., d,..., d,..., d,..., d,. '., m., m., m., m., m.0, m.., m.., m.., m \ \ \ \ \ \. \. \. \ '., s., s., s., s., s., s.., s..0, s.., s '., s., s., s., s., s., s.., s.., s.., s '., d,.0., d,.., d,..0, d,.., d,.0., d,..., d,..., d,..., d,. ''., m., m., m., m., m.0, m.., m.., m.., m ' \ \ \ \ \ \. \.0 \. \ ''., s., s.0, s., s., s., s.., s.., s.., s ''., s., s., s., s., s., s.., s.., s.., s Signals were assigned by comparison of the spectra of the enzyme products with those of the substrate, and with each other, as well as by SQC and MBC correlations.
6 0 ' ' ' 0 ' ' ' 0 ' ' ' ' ' ' 0 ' ' ' 0 b f g i j ' ' ' 0 j O ' '' '' ' '' '' ' '' '' ' O ' ' ' 0 j 0 j O ' '' '' ' '' ' ' ' ' ' ' 0 k CO ' ' 0 ' ' ' k CO ' 0 l CO MBC connectivity Figure. S MBC connectivities of enzyme products b, f, g, i, j, j, j, j, k, k and l.
7 0 ' ' ' Figure S. -NMR spectrum of b in CD OD (00 Mz) Figure S. SQC spectrum of b in CD OD (00 Mz)
8 Figure S. MBC spectrum of b in CD OD (00 Mz) 0 ' ' ' Figure S. -NMR spectrum of f in CD OD (00 Mz)
9 Figure S. SQC spectrum of f in CD OD (00 Mz) Figure S. MBC spectrum of f in CD OD (00 Mz)
10 0 ' ' ' Figure S. -NMR spectrum of g in CD OD (00 Mz) Figure S. SQC spectrum of g in CD OD (00 Mz)
11 Figure S. MBC spectrum of g in CD OD (00 Mz) ' ' 0 ' Figure S. -NMR spectrum of i in CD OD (00 Mz) 0
12 Figure S. SQC spectrum of i in CD OD (00 Mz) Figure S. MBC spectrum of i in CD OD (00 Mz)
13 ' ' ' 0 O Figure S -NMR spectrum of i in CD OD (00 Mz) ' ' ' 0 ' '' '' ' '' Figure S -NMR spectrum of i in CD OD (00 Mz)
14 '' 0 ' ' ' ' '' ' '' Figure S -NMR spectrum of i in CD OD (00 Mz) ' ' ' 0 O ' '' '' ' '' Figure S -NMR spectrum of i in CD OD (00 Mz)
15 '' '' ' '' ' O ' ' ' 0 Figure S0 -NMR spectrum of i in CD OD (00 Mz) ' ' 0 ' Figure S. -NMR spectrum of j in CD OD (00 Mz)
16 Figure S. SQC spectrum of j in CD OD (00 Mz) Figure S. MBC spectrum of j in CD OD (00 Mz)
17 0 ' ' ' Figure S -NMR spectrum of j in CD OD (00 Mz) ' ' ' 0 O Figure S -NMR spectrum of j in CD OD (00 Mz)
18 ' '' '' ' '' ' ' 0 ' Figure S -NMR spectrum of j in CD OD (00 Mz) ' '' '' ' '' 0 ' ' ' Figure S -NMR spectrum of j in CD OD (00 Mz)
19 ' ' 0 ' O ' '' '' ' '' Figure S. -NMR spectrum of j in CD OD (00 Mz) Figure S. SQC spectrum of j in CD OD (00 Mz)
20 Figure S. MBC spectrum of j in CD OD (00 Mz) ' ' '' ' '' '' ' O 0 ' Figure S. -NMR spectrum of j in CD OD (00 Mz)
21 Figure S. SQC spectrum of j in CD OD (00 Mz) Figure S. MBC spectrum of j in CD OD (00 Mz) 0
22 ' 0 O ' ' '' '' ' '' ' Figure S. -NMR spectrum of j in CD OD (00 Mz) Figure S. SQC spectrum of j in CD OD (00 Mz)
23 Figure S. MBC spectrum of j in CD OD (00 Mz) ' ' ' 0 CO Figure S. -NMR spectrum of k in CD OD (00 Mz)
24 Figure S. SQC spectrum of k in CD OD (00 Mz) Figure S. MBC spectrum of k in CD OD (00 Mz)
25 0 CO ' ' ' Figure S0. -NMR spectrum of k in CD OD (00 Mz) Figure S0. SQC spectrum of k in CD OD (00 Mz)
26 Figure S0. MBC spectrum of k in CD OD (00 Mz) ' ' ' 0 CO Figure S. -NMR spectrum of l in CD OD (00 Mz)
27 Figure S. SQC spectrum of l in CD OD (00 Mz) Figure S. MBC spectrum of l in CD OD (00 Mz)
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