为了合成一种有前途的材料,用于开发一种新型的肽/蛋白质递送系统,本文研究了壳寡糖与1-脒并吡唑盐酸盐的胍化。通过红外光谱(IR)证明了胍化壳寡糖的生产,核磁共振(NMR),和元素分析。有趣的是,我们发现胍化壳寡糖的还原端转化为环状胍结构(2-[(氨基亚氨基甲基)氨基]-2-脱氧-d-葡萄糖结构)。通过d-葡糖胺的胍化仔细证明了该反应。虽然这不是关于2-[(氨基亚氨基甲基)氨基]-2-脱氧-d-葡萄糖合成的第一次报道,它利用还原端的高反应性提供了合理的合成路线。此外,我们发现,在中性pH环境中,壳寡糖与牛血清白蛋白的相互作用较弱;胍化显著改善。胍化的壳寡糖不仅可用于开发新的药物递送系统,而且可用作几丁质酶/壳聚糖酶抑制剂和抗菌剂。
In order to synthesize a promising material for developing a novel peptide/protein delivery system, guanidinylation of chitooligosaccharides with 1-amidinopyrazole hydrochloride was investigated herein. The production of guanidinylated chitooligosaccharides was demonstrated by infrared spectroscopy (IR), nuclear magnetic resonance (NMR), and elemental analyses. Interestingly, we found that the reducing end in the guanidinylated chitooligosaccharides was converted to a cyclic guanidine structure (2-[(aminoiminomethyl)amino]-2-deoxy-d-glucose structure). This reaction was carefully proven by the guanidinylation of d-glucosamine. Although this is not the first report on the synthesis of the 2-[(aminoiminomethyl)amino]-2-deoxy-d-glucose, it has provided a rational synthetic route using the high reactivity of the reducing end. Furthermore, we found that the interaction between chitooligosaccharides and bovine serum albumin is weak when in a neutral pH environment; however, it is significantly improved by guanidinylation. The guanidinylated chitooligosaccharides are useful not only for the development of a novel drug delivery system but also as a chitinase/chitosanase inhibitor and an antibacterial agent.