2 Methylene-beta-alanine methyl ester: a toxic amino acid originating from the sponge Fasciospongia cavernosa.
N-acyl-2-methylene-beta-alanine methyl esters (A) are the main lipidic compounds in the sponge Fasciospongia cavernosa. These compounds were isolated and after methanolysis--2 methylene-beta-alanine methyl esters (AA) and free fatty acid methyl esters were obtained. The interaction of A and AA with the thiol group of cysteine was detected by Ellman's procedure. Both A and AA interact with the thiol group of cysteine in the pH range of 6.0-8.0. Both compounds were found to be strong inhibitors of glyceraldehyde triphosphate dehydrogenase (TPD) from rabbit muscle. The inhibitory effect of A and AA decreases upon addition of beef extract and other protein mixtures containing thiol groups. E. coli growth on a synthetic medium was inhibited by compound AA. Resistant E. coli varieties were isolated by techniques of enrichment cultures. Some of these resistant varieties were shown, by cross-feeding with cysteine dependent E. coli varieties, to excrete cysteine and cysteine derivatives.
D000409:Alanine / Q000031:analogs & derivatives*; D000818:Animals; D004926:Escherichia coli / Q000187:drug effects; D005987:Glyceraldehyde-3-Phosphate Dehydrogenases / Q000037:antagonists & inhibitors; D008387:Marine Toxins / Q000633:toxicity*; D011161:Porifera; D011817:Rabbits; D013997:Time Factors; D015091:beta-Alanine / Q000031:analogs & derivatives* / Q000633:toxicity
D008387:Marine Toxins; D015091:beta-Alanine; C038925:2-methylene beta-alanine methyl ester; D005987:Glyceraldehyde-3-Phosphate Dehydrogenases; D000409:Alanine