Improved approach for anchoring N alpha-9-fluorenylmethyloxycarbonylamino acids as p-alkoxybenzyl esters in solid-phase peptide synthesis.
Several Fmoc-amino acids have been esterified by use of N,N-dimethylformamide dineopentyl acetal to 2,4,5-trichlorophenyl 3'-(4''-hydroxymethyl-phenoxy)propionate, and the resultant handle derivatives were purified and then quantitatively coupled onto aminomethyl supports. Compared to literature methodology, the present procedure is preferred because: (i) extra steps to selectively protect and liberate the carboxyl of the handle are circumvented; and (ii) the additional methylene group spacer reflecting substitution of a propionyl group for an acetyl group in the handle changes the electronic parameters of the resultant p-alkoxybenzyl ester sufficiently so that the rates of acidolytic cleavage of the anchoring linkage are 2- to 3-fold increased and useful improvements in yields can be achieved.
D000596:Amino Acids; D001593:Benzyl Compounds; D055598:Chemical Phenomena; D002621:Chemistry; D005449:Fluorenes; D007202:Indicators and Reagents; D010455:Peptides / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship
D000596:Amino Acids; D001593:Benzyl Compounds; D005449:Fluorenes; D007202:Indicators and Reagents; D010455:Peptides