Chemistry & Biology
Aza-Tryptamine Substrates in Alkaloid Biosynthesis
suspension culture (150 ml) that had been subcultured for 10 days. The
cultures were allowed to incubate for an additional 7 days, at which point
the cells were filtered and ground in methanol. The methanol extract was dried,
redissolved in ethyl acetate, and washed with water. The organic layer was
concentrated, dissolved in methanol and subjected to LC-MS analysis. Ultra-
performance LC analysis was performed on an Acquity Ultra Performance
BEH C18 column with a 1.7 mm particle size, 2.1 3 100 mm dimension, and
a flow rate of 0.6 ml minꢀ1 in tandem with a Micromass LCT Premier TOF
Mass Spectrometer with an ESI source (Waters Corporation). The capillary
and sample cone voltages were 3000 V and 30 V, respectively. The desolvation
and source temperatures were 300 and 100ꢂC, respectively. The cone and
desolvation gas flow rates were 60 and 800 l hrꢀ1. Analysis was performed
with MassLynx 4.1. Compound 14 was purified from reverse phase prepara-
tive HPLC using a gradient of 0%–30% acetonitrile in water with 0.1% trifluoro-
acetic acid over 40 min.
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7-Aza-isositsirikine (3a, 16R, 19E) 14
McCoy, E., Galan, M.C., and O’Connor, S.E. (2006). Substrate specificity of
1H-NMR (600 MHz, CD3OD) d 8.25 (d, J = 3.7 Hz, 1H), 8.00 (d, J = 7.7 Hz, 1H),
7.17 (dd, J = 7.7 Hz, 4.9 Hz, 1H), 6.04 (q, J = 6.7 Hz, 1H), 3.88 (m, 3H), 3.78
(s, 3H), 3.70 (m, 3H), 3.56 (m, 2H), 3.19 (m, 1H), 3.06 (m, 1H), 2.62 (m, 2H),
2.46 (m, 2H). Exact mass (ESI-TOF): m/z calc (M+H): 356.1969, found:
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SUPPLEMENTAL DATA
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Supplemental Data include thirteen figures, six tables, and Supplemental
Experimental Procedures and can be found with this article online at http://
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ACKNOWLEDGMENTS
Pullagurla, M., Dukat, M., Roth, B.L., Setola, V., and Glennon, R.A. (2005).
5-Azatryptamine analogs as h5-HT6 serotonin receptor ligands. Med. Chem.
Res. 14, 1–18.
We acknowledge support from GM074820.
Received: August 7, 2009
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Revised: October 27, 2009
Accepted: November 13, 2009
Published: December 23, 2009
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