Phosphine-mediated one-pot thiol-ene "click" approach to polymer-protein conjugates.
We employ water-soluble organic phosphines as key reagents in a one-pot synthetic protocol where a (poly)peptide disulfide bridge is first reduced followed by subsequent reaction of the two thiols in situ with poly(monomethoxy ethylene glycol)(meth)acrylates (p(mPEG)(M)A); we use salmon calcitonin (sCT) as a disulfide bridge-containing peptide, which contains a disulfide bridge-Cys1-Cys7-that can be reduced to give two sulfhydryl units available for thiol functionalisation; bioactivity is retained.
Jones
Mathew W
MW
Department of Chemistry, University of Warwick, Coventry, UKCV4 7AL.
Mantovani
Giuseppe
G
Ryan
Sinead M
SM
Wang
Xuexuan
X
Brayden
David J
DJ
Haddleton
David M
DM
D002116:Calcitonin / Q000737:chemistry*; D004337:Drug Carriers; D010720:Phosphines / Q000737:chemistry*; D011092:Polyethylene Glycols / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013438:Sulfhydryl Compounds / Q000737:chemistry
D004337:Drug Carriers; D010720:Phosphines; D011108:Polymers; D013438:Sulfhydryl Compounds; D011092:Polyethylene Glycols; C028815:salmon calcitonin; C028210:monomethoxypolyethylene glycol; D002116:Calcitonin