Antimutagenic unusual amino acids from plants.
Five unusual amino acids were identified as antimutagens against spontaneous mutation of Salmonella typhimurium TA100: L-azetidine-2-carboxylic acid (1) from Liliaceae plants, alpha-(methylenecyclopropyl)glycine (2) from Litchi chinensis seeds, and 2-amino-4-methylhex-5-ynoic acid (3), hypoglycin A (4), and (2S,4R)-2-amino-4-hydroxyhept-6-ynoic acid (5) from Euphoria longana seeds. The absolute stereochemistry of 5 was determined by its chiral synthesis from L-allylglycine, proving that 5 is the C-4 epimer of the amino acid previously isolated from dried longan seeds.
D000596:Amino Acids / Q000302:isolation & purification* / Q000494:pharmacology; D000963:Antimetabolites / Q000302:isolation & purification / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects / Q000235:genetics; D009152:Mutagenicity Tests; D009154:Mutation; D010936:Plant Extracts / Q000494:pharmacology; D010944:Plants / Q000032:analysis*; D012486:Salmonella typhimurium / Q000187:drug effects / Q000235:genetics; D012639:Seeds / Q000032:analysis; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000596:Amino Acids; D000963:Antimetabolites; D010936:Plant Extracts