Syntheses of [C-14]-detergents: octaethylene-glycol-[1-C-14]-dodecylether,[1-C-14]-dodecyl-beta-D-maltoside and dibromo-analogues

Octaethylene-glycol-dodecylether and dodecyl-beta -D-maltoside are two wide ly used detergents in membrane protein studies. We describe here the synthe sis of the C-14-labelled brominated analogues, and of the C-14-labelled for ms. [1-C-14]-5,6-Dibromo-dodecylether was prepared by coupling [1-C-14]-(Z) -1-bromo-dodec-5-ene with octaethylene glycol followed by bromination. [1-C -14]-5,6-Dibromo-dodecyl-beta -D-maltoside was synthesised from [1-C-14]-(Z )-dodec-5-en-1-ol via a coupling with alpha -bromohepta-O-acetyl-maltose fo llowed by a deprotection step and bromination. Following similar methods, o ctaethylene-glycol-[1-C-14]-dodecylether and [1-C-14]-dodecyl-beta -D-maito side were also obtained. Copyright (C) 2001 John Wiley & Sons, Ltd.