Biosynthesis of the indolizidine alkaloid cyclizidine: incorporation of singly and doubly labelled precursors
Canadian Journal of Chemistry1994Vol. 72(1), pp. 131–141
Citations Over Time
Abstract
Incorporation of CH 3 13 C 18 O 2 Na and CD 3 CH 2 13 CO 2 Na into the indolizidine alkaloid cyclizidine 1, 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.
Related Papers
- → Regulating the molar fraction of 4-hydroxybutyrate in poly(3-hydroxybutyrate-4-hydroxybutyrate) biosynthesis by Ralstonia eutropha using propionate as a stimulator(2000)35 cited
- → A concise asymmetric synthesis of 5,8-disubstituted indolizidine alkaloids. Total synthesis of (−)-indolizidine 209B(2002)33 cited
- → Biosynthesis of the indolizidine alkaloid, cyclizidine(1987)13 cited
- → A General Approach to 3-n-Butyl-5-alkylindolizidines: Total Synthesis of (−)-Indolizidine 195B(2007)21 cited
- → Biosynthesis of asteltoxin by cultures of Emericella variecolor. The role of propionate in the biosynthesis and evidence for a 1,2-bond migration in the formation of the bistetrahydrofuran moiety(1984)17 cited