Chemistry Commons^™

Synthesis Of Phenyl Carbamoylated Guanidine Functionalized Chitosan, Eduardo Hernandez Requejo

FIU Electronic Theses and Dissertations

The lack of solubility of the chitosan in organic solvents hinders its potential for chemical modifications. For this reason, it was hypothesized that the insertion of the phenyl carbamoylated guanidine moiety could lead to increased solubility in DMSO and new potential modifications and uses.

This research involved the synthesis of S-methyl phenyl carbamoylated guanidine (SMPCG) starting from the commercially available S-methyl isothiourea. This was followed by the reaction of the SMPCG with chitosan to yield phenyl carbamoylated guanidine functionalized chitosan (PCGCs) with a degree of substitution of 14%.

The chitosan derivative is fully soluble in DMSO and partially in DMF. …

Synthesis And Characterization Of Chitosan Derivatives Intended For Gene Delivery Applications, Alex M. Mcmullen

MSU Graduate Theses

Chitosan has been studied as a non-viral vector capable of efficient gene delivery due to its favorable properties such as biodegradability, biocompatibility, and is non-toxic to mammalian cells. Incorporating electrostatic interactions in non-viral vectors enhance the vector permeability. This work focuses on two parts. Firstly, cationic chitosan derivatives were synthesized using quarternary ammonium and phosphonium groups. This was achieved by coupling carboxylic acid ligands with these quarternary groups to chitosan through an amide bond. The carboxylic acid ligands were synthesized from 4-methylbenzoic acid and either triethyl phosphine or triethyl amine. The ligand was then attached to chitosan through an amide …