Synthesis of Phenyl Carbamoylated Guanidine Functionalized Chitosan

Authors

Eduardo Hernandez Requejo, Florida International UniversityFollow

Document Type

Thesis

Degree

Master of Science (MS)

Major/Program

Chemistry

First Advisor's Name

Joong Ho Moon

First Advisor's Committee Title

Committee chair

Second Advisor's Name

Stanislaw Wnuk

Second Advisor's Committee Title

committee member

Third Advisor's Name

Watson Lees

Third Advisor's Committee Title

committee member

Keywords

chitosan, guanylurea, guanidinylation, carbamoylated, guanidine

Date of Defense

6-14-2022

Abstract

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. This modified polymer will be used in future experiments in protein delivery, antimicrobial activity, and siRNA transfection. Future research is also planned to obtain PCGCs with different degrees of substitution.

Identifier

FIDC010815

Recommended Citation

Hernandez Requejo, Eduardo, "Synthesis of Phenyl Carbamoylated Guanidine Functionalized Chitosan" (2022). FIU Electronic Theses and Dissertations. 5124.
https://digitalcommons.fiu.edu/etd/5124