Khan S A, Merkel G J, Becker J M, Naider F
Int J Pept Protein Res. 1981 Feb;17(2):219-30. doi: 10.1111/j.1399-3011.1981.tb01985.x.
The synthesis of His-Trp-Leu-Gln-Leu-Lys-Pro-Gly-Gln-Pro-Met-Tyr, the dodecapeptide alpha-mating factor from Saccharomyces cerevisiae, and its Ala2- and Cha2-(beta-cyclohexylalanine) analogs are reported. Peptides were synthesized in solution using a combination of mixed anhydride and 1-hydroxybenzotriazole accelerated active ester coupling procedures. Dilute methanesulfonic acid (0.1-0.2 M) in methylene chloride-formic acid solution was employed to specifically remove the tert.-butoxycarbonyl group in the presence of the benzyloxycarbonyl group. Free peptides were obtained using catalytic transfer hydrogenation with formic acid as the hydrogen donor followed by mild acidolysis with trifluoroacetic acid. The alpha-factor and the Cha2-analog exhibited almost equal ability to cause "shmooing" of a-mating types of S. cerevisiae whereas the Ala2-analog exhibited no activity in this assay. These results differ with structure-activity studies reported on the tridecapeptide alpha-factor.
报道了来自酿酒酵母的十二肽α-交配因子His-Trp-Leu-Gln-Leu-Lys-Pro-Gly-Gln-Pro-Met-Tyr及其Ala2-和Cha2-（β-环己基丙氨酸）类似物的合成。使用混合酸酐和1-羟基苯并三唑加速活性酯偶联程序的组合在溶液中合成肽。在二氯甲烷-甲酸溶液中使用稀甲磺酸（0.1-0.2 M）在苄氧羰基存在下特异性去除叔丁氧羰基。使用甲酸作为氢供体的催化转移氢化，然后用三氟乙酸进行温和酸解，得到游离肽。α-因子和Cha2-类似物在引起酿酒酵母α-交配型“成帽”方面表现出几乎相同的能力，而Ala2-类似物在该测定中没有活性。这些结果与关于十三肽α-因子的结构-活性研究不同。
