Fraczyk Justyna, Walczak Małgorzata, Kaminski Zbigniew J
Institute of Organic Chemistry, Lodz University of Technology, 90-924, Lodz, Poland.
J Pept Sci. 2018 Feb;24(2). doi: 10.1002/psc.3063.
Two new rigid bi-aromatic linkers for synthesis of peptide arrays by SPOT methodology were obtained from cellulose treated with 2,4-dichloro-6-methoxy-1,3,5-triazine. Reaction with m-phenylenediamine gave non-cleavable TYPE I linker which enabled attachment of the peptides via resistant to harsh reaction conditions amide, ether, and amine bonds. Reaction with 3-Fmoc-aminobenzoic acid followed by thermal isomerization of the intermediate "superactive" ester producing an amide-like bond gave TYPE II linker that was very stable during peptide synthesis. However, the peptide was cleavable, with fragment of the linker, in the presence of 1 M LiOH solution. The uniform loading of the cellulose and efficient synthesis of the peptide array was achieved by using N-(4,6-dimethoxy-1,3,5-triazin-1-yl)-N-methylmorpholinium 4-toluenesulfonate as the coupling reagent.
通过用2,4-二氯-6-甲氧基-1,3,5-三嗪处理纤维素，获得了两种用于通过SPOT方法合成肽阵列的新型刚性双芳族连接体。与间苯二胺反应得到不可裂解的I型连接体，该连接体能够通过耐苛刻反应条件的酰胺键、醚键和胺键连接肽。与3-Fmoc-氨基苯甲酸反应，然后中间体“超活性”酯进行热异构化生成类酰胺键，得到II型连接体，其在肽合成过程中非常稳定。然而，在1 M LiOH溶液存在下，肽可与连接体片段一起裂解。通过使用N-(4,6-二甲氧基-1,3,5-三嗪-1-基)-N-甲基吗啉鎓4-甲苯磺酸盐作为偶联试剂，实现了纤维素的均匀负载和肽阵列的高效合成。
