Studies on the biosynthesis of asperparaline A: origin of the spirosuccinimde ring system.
The primary amino acid building blocks that constitute asperparaline A have been determined through feeding and incorporation of 13C-labeled intermediates. The beta-methyl proline residue is constituted from (S)-isoleucine, the novel spiro-succinime moiety is derived from the oxidative degradation of (S)-tryptophan, and (S)-adenosylmethionine contributes the two N-methyl residues. In addition, it was found that the incorporation of 13C-labeled acetate into the single isoprene unit clearly demonstrates that the isoprene moiety is derived from the mevalonate pathway.
Gray
Chandele R
CR
Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
Sanz-Cervera
Juan F
JF
Silks
Louis A
LA
Williams
Robert M
RM
D000470:Alkaloids / Q000096:biosynthesis*; D001230:Aspergillus / Q000378:metabolism*; D002247:Carbon Isotopes; D045782:Hemiterpenes / Q000378:metabolism; D007532:Isoleucine / Q000378:metabolism; D019906:Nuclear Magnetic Resonance, Biomolecular; D009943:Organophosphorus Compounds / Q000378:metabolism; D010879:Piperazines; D021241:Spectrometry, Mass, Electrospray Ionization; D013141:Spiro Compounds / Q000378:metabolism*; D013388:Succinimides / Q000378:metabolism*; D014364:Tryptophan / Q000378:metabolism
D000470:Alkaloids; D002247:Carbon Isotopes; D045782:Hemiterpenes; D009943:Organophosphorus Compounds; D010879:Piperazines; D013141:Spiro Compounds; D013388:Succinimides; C109708:aspergillimide; D007532:Isoleucine; C043060:3,3-dimethylallyl pyrophosphate; D014364:Tryptophan