Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-383 Wroclaw, Poland.
J Pept Sci. 2010 Jan;16(1):31-9. doi: 10.1002/psc.1191.
Microwave-assisted (MW) reactions are of special interest to the chemical community due to faster reaction times, cleaner reactions and higher product yields. The adaptation of MW to solid phase peptide synthesis resulted in spectacular syntheses of difficult peptides. In the case of Merrifield support, used frequently in synthesis of special peptides, the conditions used in product cleavage are not compatible with off-resin monitoring of the reaction progress. The application of MW irradiation in product removal from Merrifield resin using trifluoroacetic acid (TFA) was investigated using model tetrapeptides and the effects were compared with standard trifluoromethanesulphonic acid (TFMSA) cleavage using elemental analysis as well as chromatographic (HPLC) and spectroscopic (IR) methods. The deprotection of benzyloxycarbonyl and benzyl groups in synthetic bioactive peptides was analyzed using LC-MS and MS/MS experiments. In a 5 min microwave-assisted TFA reaction at low temperature, the majority of product is released from the resin, making the analytical scale MW-assisted procedure a method of choice in monitoring the reactions carried out on Merrifield resin due to the short reaction time and compatibility with HPLC and ESI-MS conditions.
微波辅助（MW）反应由于反应时间更快、反应更清洁、产物收率更高，因此受到化学界的特别关注。MW 技术在固相肽合成中的应用导致了困难肽的壮观合成。在 Merrifield 支持物的情况下，经常用于合成特殊肽，用于产物切割的条件与树脂外监测反应进展不兼容。使用三氟乙酸（TFA）从 Merrifield 树脂中去除产物的 MW 辐射应用进行了研究，使用模型四肽进行了研究，并使用元素分析以及色谱（HPLC）和光谱（IR）方法对其进行了比较。使用 LC-MS 和 MS/MS 实验分析了合成生物活性肽中苄氧羰基和苄基的脱保护。在 5 分钟的低温微波辅助 TFA 反应中，大部分产物从树脂中释放出来，使得分析规模的 MW 辅助程序成为监测在 Merrifield 树脂上进行的反应的首选方法，因为反应时间短，并且与 HPLC 和 ESI-MS 条件兼容。
