Abstract
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.
Highlights
Chitosan (CS) is an amino polysaccharide, composed of β-d-glucosamine (>60%) and β-d-N-acetylglucosamine linking through a β-1,4-linkage and obtained by the deacetylation of chitin [1]
Guanidinylation was performed with 3.8 equivalents of AP toward an amino group in was with
Notethat thatalthough althoughthe thecyclic cyclic guanidine guanidine structure structure on isomers after guanidinylation
Summary
Chitosan (CS) is an amino polysaccharide, composed of β-d-glucosamine (>60%) and β-d-N-acetylglucosamine linking through a β-1,4-linkage and obtained by the deacetylation of chitin [1]. Chitosans with degree of polymerization (DP) < 20 and that have an average molecular weight of up to 3900 Da are called chitooligosaccharides (COSs) [2]. Common chitosans are insoluble in a neutral water, COSs are highly soluble. COSs are reported to possess remarkable biological properties [3,4], undoubtedly making them attractive materials for developing novel pharmaceuticals. Improvement of the low biomembrane permeability of peptide/protein drugs is a key aspect of pharmaceutical sciences [5]. Cell-penetrating peptide (CPP) has attracted great attention as a promising [6]. Their their cytotoxicity cytotoxicity and the innate innate promising material material for for delivering delivering such such drugs drugs into into cells cells [6]
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