TY - JOUR
T1 - Improved approach for anchoring Nα‐9‐fluorenylmethyloxycarbonylamino acids as p‐alkoxybenzyl esters in solid‐phase peptide synthesis
AU - ALBERICIO, FERNANDO
AU - BARANY, GEORGE
PY - 1985/7
Y1 - 1985/7
N2 - Several Fmoc‐amino acids have been esterified by use of N,N‐dimethylformamide dineopentyl acetal (2) to 2,4,5‐trichlorophenyl 3‘‐(4“‐hydroxymethyl‐phenoxy)propionate (7), and the resultant handle derivatives (5) 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.
AB - Several Fmoc‐amino acids have been esterified by use of N,N‐dimethylformamide dineopentyl acetal (2) to 2,4,5‐trichlorophenyl 3‘‐(4“‐hydroxymethyl‐phenoxy)propionate (7), and the resultant handle derivatives (5) 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.
KW - 2,4,5‐trichlorophenyl 3‘‐(4“‐hydroxy‐methylphenoxy)propionate handle
KW - N,N‐dimethylformamide dineopentyl acetal
KW - N‐9‐fluorenylmethyloxycarbonylamino acids
KW - p‐alkoxybenzyl esters
KW - solid‐phase peptide synthesis
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U2 - 10.1111/j.1399-3011.1985.tb03182.x
DO - 10.1111/j.1399-3011.1985.tb03182.x
M3 - Article
C2 - 4055231
AN - SCOPUS:0022091975
SN - 0367-8377
VL - 26
SP - 92
EP - 97
JO - International Journal of Peptide and Protein Research
JF - International Journal of Peptide and Protein Research
IS - 1
ER -