High yield immobilisation of a puromycin analogue for the solid support synthesis of aminoacyl-tRNA fragments

Nhat Quang Nguyen-Trung, Silvia Terenzi, Gerd Scherer, and Peter Strazewski
Organic Letters 2003, 5, 2603-2606

High yield immobilisation of a puromycin analogue for the solid support synthesis of aminoacyl-tRNA fragments

An efficient procedure for the immobilisation of 3'-deoxy-3'-(O-methyltyrosyl)aminoadenosine was developed. A polyethylene glycol-derived diacid linker/spacer was attached to aminomethyl polystyrene. Coupling of the 2'-hydroxy instead of the 2'-O-succinylated ribonucleoside resulted in high immmobilisation yields (over 80%) and allowed for the recovery of valuable unreacted material. This specific procedure should be applicable to other ribonucleosides containing a bulky modification at the 3'-position and can be used for the stepwise construction of 3'-aminoacyl- or 3'-peptidyl-RNA conjugates.