Aza-Tryptamine Substrates in Monoterpene Indole Alkaloid Biosynthesis

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Presentation transcript:

Aza-Tryptamine Substrates in Monoterpene Indole Alkaloid Biosynthesis Hyang-Yeol Lee, Nancy Yerkes, Sarah E. O'Connor Chemistry & Biology Volume 16, Issue 12, Pages 1225-1229 (December 2009) DOI: 10.1016/j.chembiol.2009.11.016 Copyright © 2009 Elsevier Ltd Terms and Conditions

Figure 1 The Aza-indole Moiety (Highlighted in Red) in Natural and Synthetic Compounds (A) Aza-indoles in natural products. (B) Aza-indole moiety in an indole natural product analog. (C) Synthetic pharmaceutically important compounds containing an aza-indole group. Chemistry & Biology 2009 16, 1225-1229DOI: (10.1016/j.chembiol.2009.11.016) Copyright © 2009 Elsevier Ltd Terms and Conditions

Figure 2 Synthesis of Aza-tryptamine Compounds 1-4 Chemistry & Biology 2009 16, 1225-1229DOI: (10.1016/j.chembiol.2009.11.016) Copyright © 2009 Elsevier Ltd Terms and Conditions

Figure 3 Reaction of Aza-tryptamines in Monoterpene Indole Alkaloid Biosynthesis (A) Reaction of aza-tryptamine compounds 1-4 in a Pictet-Spengler reaction. (B) Formation of downstream alkaloid and aza-alkaloid products. Chemistry & Biology 2009 16, 1225-1229DOI: (10.1016/j.chembiol.2009.11.016) Copyright © 2009 Elsevier Ltd Terms and Conditions

Figure 4 LC-MS Spectra Showing Production of New Compounds by Catharanthus roseus When Supplemented with Deglycosylated Strictosidine Derived from 1 and 4 Starred peaks indicate compounds found only in cultures supplemented with deglycosylated strictosidine derived from 1 or 4. LC-MS spectra showing the results of feeding deglycosylated strictosidine 11 derived from natural tryptamine 5 to cell cultures are shown in the Supplemental Data. Chemistry & Biology 2009 16, 1225-1229DOI: (10.1016/j.chembiol.2009.11.016) Copyright © 2009 Elsevier Ltd Terms and Conditions