Type
Text
Type
Thesis
Advisor
Rudick, Jonathan | Grubbs, Robert B | Chu, Benjamin.
Date
2011-12-01
Keywords
Chemistry--Polymer chemistry
Department
Department of Chemistry
Language
en_US
Source
This work is sponsored by the Stony Brook University Graduate School in compliance with the requirements for completion of degree.
Identifier
http://hdl.handle.net/11401/71360
Publisher
The Graduate School, Stony Brook University: Stony Brook, NY.
Format
application/pdf
Abstract
Amphiphilic block copolymers are polymers that consist of hydrophobic and hydrophilic blocks. These polymers have been of interest because of their potential use in medical applications such as gene delivery. The gene delivery vector that our group is currently synthesizing is an amphiphilic tri-arm star copolymer. The tri-arm star copolymer consists of a hydrophillic polyethylene glycol (PEG), a hydrophobic poly (lactic acid) (PLA) block, and a short cleavable oligolysine chain that will complex with DNA. In this document, model studies of lactic acid (LA) polymerization from 3-hydroxy-N-(2-methoxyethyl)-2-[(phenylmethoxy)carbonyl] propanamide (compound 1), and the synthesis of the components of the third arm; which are the cleavable disulfide compound N-succinimidyl 3-(2-pyridyldithio) propionate (SPDP) and the short oligolysine peptides chain. Model studies of LA polymerization were conducted using tin (II) octanoate as catalyst and compound (1) as the initiator for ring opening polymerization. The ring opening polymerizations were conducted in both bulk and solution; with target molecular weights ranging from 2,000 to 10,000 g/mol. The components necessary to make the third arm of the tri-arm star block copolymer are SPDP and oligolysine peptides. The synthesis of SPDP was accomplished in a two-step reaction, done according to literature. Oligolysine-rich peptides KKC and KKKC were prepared by solution phase peptide synthesis using orthogonal protecting groups,56 pages
Recommended Citation
Ngai, Chai Kit, "Synthesis of Components for Amphiphilic Tri-Arm Star Copolymer for Gene Delivery" (2011). Stony Brook Theses and Dissertations Collection, 2006-2020 (closed to submissions). 566.
https://commons.library.stonybrook.edu/stony-brook-theses-and-dissertations-collection/566