Spiro Iminosugars: Structural Diversity and Synthetic Strategies

International audienceFrom their discovery in the late 1960s, iminosugars have undergone an expansion from an area of science limited to a few researchers to a field that now attracts the interest of members of the whole synthetic organic chemistry community. Indeed, many tasks concern structural modifications of standard iminosugars in order to improve their biological and pharmacological properties. In this way, the introduction of an adjoining spirocycle afforded unprecedented polyhydroxy-azaspiranes, the structures and syntheses of which are presented in this chapter. Special attention is paid to the key steps involved in the generation of the pivotal quaternary spiro atom

Structure and Function of Enzymes Involved in the Biosynthesis of Tropane Alkaloids

Tropane alkaloids are found in a scattered distribution among the angiosperm families including members within the Solanaceae, Erythroxylaceae, Convolvulaceae, and Brassicaceae. Recent studies regarding the origins of tropane production provide strong evidence for a polyphyletic origin, suggesting that novel enzymes from different gene families have been recruited during the course of flowering plant evolution. Tropane alkaloid biosynthesis is best documented on the molecular genetic and biochemical level from solanaceous species. Regardless of the system chosen, there are currently gaps in the knowledge of enzyme structure-function relationships and how they influence tropane alkaloid biosynthesis. Obtaining insights on structure-function relationships of tropane biosynthetic enzymes is critical to understanding regulation, turnover, and flux of metabolites through the pathway. In this review, we discuss the current state of knowledge regarding structure-function relationships of the known steps involved in tropane biosynthesis.This is a post-peer-review, pre-copyedit version of a chapter published as Kim, Neill, Benjamin Chavez, Charles Stewart, and John C. D’Auria. "Structure and Function of Enzymes Involved in the Biosynthesis of Tropane Alkaloids." In Tropane Alkaloids (Srivastava V., Mehrotra S., Mishra S., eds.) 2021: 21-50. The final authenticated version is available online at DOI: 10.1007/978-981-33-4535-5_2. Posted with permission.</p