Improved approach for anchoring Nα‐9‐fluorenylmethyloxycarbonylamino acids as p‐alkoxybenzyl esters in solid‐phase peptide synthesis
- 1 July 1985
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 26 (1) , 92-97
- https://doi.org/10.1111/j.1399-3011.1985.tb03182.x
Abstract
Several Fmoc[9-fluorenylmethyloxycarbonyl]-amino acids were esterified by use of N,N-dimethylformamide dineopentyl acetal to 2, 4, 5-trichlorophenyl 3''-(4"-hydroxymethylphenoxy)propionate and the resultant handle derivatives were purified and then quantitatively coupled onto aninomethyl 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.Keywords
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