Andruszkiewicz R, Chmara H, Milewski S, Borowski E
Int J Pept Protein Res. 1986 May;27(5):449-53. doi: 10.1111/j.1399-3011.1986.tb01041.x.
Several analogues of N3-fumaramoyl-L-2,3-diaminopropanoic acid were synthesized and evaluated for inhibition of glucosamine-6-phosphate synthetase activity. The syntheses were accomplished by acylation reaction of N2-tert.-butoxycarbonyl-L-2,3-diaminopropanoic acid (Boc-A2pr) or N2-tert.-butoxycarbonyl-L-2,4-diaminobutanoic acid (Boc-A2-bu) with the N-succinimidoyl esters of several derivatives of alpha, beta-unsaturated acids 2a-d followed by deprotection of the Boc groups. The obtained compounds were tested for inhibition of glucosamine synthetase isolated from Salmonella typhimurium and Saccharomyces cerevisiae. The results indicated that among the synthesized compounds, N3-4-methoxyfumaroyl-L-2,3-diaminopropanoic acid (FMDP) was the most powerful inhibitor of glucosamine synthetase.
合成了几种N3-富马酰-L-2,3-二氨基丙酸类似物，并对其抑制6-磷酸葡萄糖胺合成酶活性的能力进行了评估。合成过程是通过N2-叔丁氧羰基-L-2,3-二氨基丙酸（Boc-A2pr）或N2-叔丁氧羰基-L-2,4-二氨基丁酸（Boc-A2-bu）与几种α,β-不饱和酸2a-d衍生物的N-琥珀酰亚胺酯进行酰化反应，然后脱除Boc基团来完成的。对所得到的化合物进行了测试，以考察其对从鼠伤寒沙门氏菌和酿酒酵母中分离出的葡萄糖胺合成酶的抑制作用。结果表明，在所合成的化合物中，N3-4-甲氧基富马酰-L-2,3-二氨基丙酸（FMDP）是葡萄糖胺合成酶最有效的抑制剂。
