6533b7d7fe1ef96bd12690e7

RESEARCH PRODUCT

"A versatile post-polymerization modification method for polyglutamic acid: synthesis of orthogonal reactive polyglutamates and their use in ""click chemistry"""

Aroa Duro-castanoMatthias BarzMaría J. Vicent

subject

Polymers and PlasticsOrganic ChemistryPolyglutamic acidBioengineering02 engineering and technologyConjugated system010402 general chemistry021001 nanoscience & nanotechnology01 natural sciencesBiochemistryCombinatorial chemistryOrganic mediaChloride0104 chemical scienceschemistry.chemical_compoundchemistryPEGylationClick chemistrymedicineOrganic chemistrySurface modification0210 nano-technologyPost polymerizationmedicine.drug

description

In this article we describe a versatile methodology for the synthesis of polyglutamic acid (PGA) derivatives bearing orthogonal reactive sites. The reactive groups enable selective conjugation chemistry by copper catalyzed azide-alkyne coupling (CuAAC). PGA was derived in aqueous media as well as in organic media using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methyl morpholinium chloride (DMTTM) salts. The spectra of attached chemical moieties ranges from simple PEGylation with 2,5,8,11,14,17,20-heptaoxadocosan-22-amine (mEG(6)NH2) to the incorporation of propargylamine, 11-azido-3,6,9-trioxaundecan-1-amine (NH2-EG(2)N-3), and 20-azido-3,6,9,12,15,18-hexaoxaicosan-1-amine (NH2-EG(6)N-3). Herein, it is demonstrated that the degree of functionalization can be easily controlled within this one pot reaction. Additionally, we report conditions for the CuAAC with various PGA derivatives, which can be employed for site-specific conjugation of either hydrophilic or hydrophobic compounds.

yearjournalcountryeditionlanguage
2013-01-01