Vo-Quang Y, Carniato D, Vo-Quang L, Lacoste A M, Neuzil E, Le Goffic F
J Med Chem. 1986 Apr;29(4):579-81. doi: 10.1021/jm00154a024.
DL-(1-Amino-2-propenyl)phosphonic acid was synthesized through the sequential oxidation, sulfoxide elimination, and deprotection of diphenyl [1-[(benzyloxycarbonyl)amino]-3-(phenylthio)propyl] phosphonate. This analogue of vinylglycine is a strong inhibitor of the alanine racemases from Pseudomonas aeruginosa and Streptococcus faecalis and of the D-Ala:D-Ala ligase from this latter species. This molecule is ineffective against the whole bacterial cells. Unlike vinylglycine, this unsaturated phosphonate does not inhibit the following mammalian enzymes: aspartate aminotransferase, alanine aminotransferase, D-amino acid oxidase, which indicates its specificity. Thus, its incorporation in a peptide structure could induce interesting antimicrobial properties.
DL-(1-氨基-2-丙烯基)膦酸是通过对二苯基[1-[(苄氧羰基)氨基]-3-(苯硫基)丙基]膦酸酯进行顺序氧化、亚砜消除和脱保护反应合成的。这种乙烯基甘氨酸类似物是铜绿假单胞菌和粪肠球菌丙氨酸消旋酶以及后一种菌的D-Ala:D-Ala连接酶的强效抑制剂。该分子对整个细菌细胞无效。与乙烯基甘氨酸不同，这种不饱和膦酸酯不抑制以下哺乳动物酶：天冬氨酸转氨酶、丙氨酸转氨酶、D-氨基酸氧化酶，这表明了它的特异性。因此，将其掺入肽结构中可能会诱导出有趣的抗菌特性。
