F. J. Leeper, S. E. Shaw and P. Satish
"The Biosynthesis of Cyclizidine: Incorporation of Singly and Doubly Labelled Precursors"
Can. J. Chem., 1994, 72, 131-141. Full Text
Incorporation of isotopically labelled forms of CH3CO2Na and CH3CH2CO2Na into the indolizidine alkaloid cyclizidine, produced by Streptomyces species NCIB 11649, shows that the oxygen attached to C-2 is derived intact from acetate and that the cyclopropyl ring is derived from a single intact propionate unit. However, the level and stereochemistry of the incorporation of deuteriated sodium propionate indicates that it undergoes unexpected modification during incorporation into the cyclopropyl ring.
Department of Chemistry
University of Cambridge