用L-高丝氨酸内酯的氢溴酸盐与酰氯在Schotten-Baumann条件下反应,合成了6种N-酰基-L-高丝氨酸内酯类(AHLs)信号分子:N-丁酰基-L-高丝氨酸内酯、N-己酰基-L-高丝氨酸内酯、N-辛酰基-L-高丝氨酸内酯、N-癸酰基-L-高丝氨酸内酯、N-十二酰基-L-高丝氨酸内酯和N-十四酰基-L-高丝氨酸内酯,通过红外、核磁共振仪、气相-质谱联用仪对所有化合物进行了结构表征和纯度分析。同时检测合成的6种化合物对污损硅藻-柱鞘藻(Cylindrothecasp.)生长的影响,结果表明:合成的信号分子除侧链最短的N-丁酰基-L-高丝氨酸内酯外,其它在高浓度下均能抑制柱鞘藻的生长,其中C12-HSL和C14-HSL在较低浓度下对柱鞘藻的生长也具有明显的抑制效应。
Six N-acyl-L-homoserine lactone derivatives(AHLs)were synthesized via reaction of S-(–)-α-Amino-γ-butyrolactone hydrobromide with a variety of acid chlorides and the structures were N-butanoyl-L-homoserine lactone,N-hexanoyl-L-homoserine lactone,N-octanoyl-L-homoserine lactone,Ndecanoyl-L-homoserine lactone,N-dodecanoyl-L-homoserine lactone and N-tetradecanoyl-L-homoserine lactone,which were confirmed by IR,1 H NMR and 13 C NMR,and GC-MS.The effects of synthetic AHLs on the growth of the fouling diatomCylindrothecasp.in the 96-well plate were studied.The results showed that the Cylindrotheca sp.could sense a range of different AHL molecules and all synthetic AHLs inhibited the growth of Cylindrothecasp.at the concentrations of above 10mg/L except for the shortest side chain,N-butanoyl-L-homoserine lactone.In addition,it was found that C12-HSL and C14-HSL tended to result in the inhibition on the growth of Cylindrothecasp.under the lower concentrations.