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Articles by Ryan Alam
Biosynthesis of cinchona alkaloids
Abstract Cinchona alkaloids, which have been studied for more than 250 years, are plant-derived natural products that have collectively had a substantial impact in medicine and basic science1,2,3,4,5. Examples of cinchona alkaloids include quinine, a historically important antimalarial drug, and cinchonidine, a chiral catalyst widely used in process chemistry. However, it is still largely unknown how plants synthesize these well-known compounds.
Discovery of iridoid cyclase completes the iridoid pathway in asterids - Nature Plants
Abstract Iridoids are specialized monoterpenes ancestral to asterid flowering plants1,2 that play key roles in defence and are also essential precursors for pharmacologically important alkaloids3,4. The biosynthesis of all iridoids involves the cyclization of the reactive biosynthetic intermediate 8-oxocitronellyl enol.
Enzymatic epimerization of monoterpene indole alkaloids in kratom - Nature Chemical Biology
Abstract Monoterpene indole alkaloids (MIAs) are a large, structurally diverse class of bioactive natural products. These compounds are biosynthetically derived from a stereoselective Pictet–Spengler condensation that generates a tetrahydro-β-carboline scaffold characterized by a 3S stereocenter. However, a subset of MIAs contains a noncanonical 3R stereocenter. Here we report the basis for 3R-MIA biosynthesis in Mitragyna speciosa (kratom).
Ipecac alkaloid biosynthesis in two evolutionarily distant plants - Nature Chemical Biology
Abstract Ipecac alkaloids are medicinal monoterpenoid-derived tetrahydroisoquinoline alkaloids found in two distantly related plants: Carapichea ipecacuanha (Gentianales) and Alangium salviifolium (Cornales). Here we provide evidence suggesting that both plants initiate ipecac alkaloid biosynthesis through a nonenzymatic Pictet–Spengler reaction and we elucidate the biosynthetic fate of both the 1R and 1S stereoisomers that are produced in this nonstereoselective reaction.
Incorporation of nitrogen in antinutritional Solanum alkaloid biosynthesis - Nature Chemical Biology
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Abstract Steroidal glycoalkaloids (SGAs) are specialized metabolites produced by hundreds of Solanum species including food crops, such as tomato, potato and eggplant. Unlike true alkaloids, nitrogen is introduced at a late stage of SGA biosynthesis through an unknown transamination reaction. Here, we reveal the mechanism by which GLYCOALKALOID METABOLISM12 (GAME12) directs the biosynthesis of nitrogen-containing steroidal alkaloid aglycone in Solanum.
By Dagny Grzech, Samuel J. Smit, Ryan Alam, Lorenzo Caputi, Benjamin R. Lichman, Sarah O'Connor Verified, Asaph Aharoni
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Nature
Verified
Accessing Dihydropyrrolo[3,4‐b]indol‐1(2H)‐ones via Pd‐Catalyzed Intramolecular Aminocarbonylative Ring Closure
Abstract Present in a number of small molecule derivatives that display a wide range of biological activities, the dihydropyrrolo[3,4-b]indol-(2H)-one (DHPI) core represents an underexplored heterocyclic scaffold. Given the pharmaceutical potential of the DHPI motif, the development of synthetic methodologies that would facilitate their expedient assembly would be highly desirable.
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