Wang Xiaoji, Feng Junmin, Xu Zhengshuang, Ye Tao, Meng Yi, Zhang Zhiyu
School of Life Science, Jiangxi Science and Technology Normal University, Nanchang 330013, China.
Laboratory of Chemical Genomics, Engineering Laboratory for Chiral Drug Synthesis, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, University Town of Shenzhen, Xili, Nanshan District, Shenzhen 518055, China.
Mar Drugs. 2017 Feb 27;15(3):58. doi: 10.3390/md15030058.
Nostosins A and B were isolated from a hydrophilic extract of Nostoc sp. strain from Iran, which exhibits excellent tryps inhibitory activity. Nostosin A was the most potent natural tripeptide aldehyde as trypsin inhibitor up to now. Both R- and S-2-hydroxy-4-(4-hydroxy-phenyl) butanoic acid (Hhpba) were prepared and incorporated into the total synthesis of nostosin B, respectively. Careful comparison of the NMR spectra and optical rotation data of synthetic nostosin B (1a and 1b) with the natural product led to the unambiguous identification of the R-configuration of the Hhpba fragment, which was further confirmed by co-injection with the authentic sample on HPLC using both reversed phase column and the chiral AD-RH column.
诺斯托辛A和B是从伊朗的一种念珠藻属菌株的亲水性提取物中分离出来的，该提取物具有出色的胰蛋白酶抑制活性。诺斯托辛A是迄今为止最有效的天然三肽醛类胰蛋白酶抑制剂。分别制备了R-和S-2-羟基-4-(4-羟基苯基)丁酸（Hhpba），并将其纳入诺斯托辛B的全合成中。通过将合成的诺斯托辛B（1a和1b）的核磁共振谱和旋光数据与天然产物进行仔细比较，明确鉴定了Hhpba片段的R-构型，通过在高效液相色谱上使用反相柱和手性AD-RH柱与真实样品共注射进一步证实了这一点。
