TY - JOUR
T1 - Acidolytic cleavage of tris(alkoxy)benzylamide (PAL) “internal reference” amino acyl (IRAA) anchoring linkages
T2 - validation of accepted procedures in solid‐phase peptide synthesis (SPPS)
AU - ALBERICIO, FERNANDO
AU - Barany, George
PY - 1993/3
Y1 - 1993/3
N2 - Under the normal conditions of acidolytic cleavage/deprotection of tris(a1koxy)benzylamide (PAL) anchoring linkages in Fmoc solid‐phase peptide synthesis (SPPS), product release occurs by a straightforward single‐step pathway. A recently reported cleavage of the NH‐VH bond of an amino acyl residue adjacent to PAL [see Int. J. Peptide Protein Res.38, 146–153 (1991)] could not be confirmed in novel experiments incorporating a double “internal reference” amino acid (IRAA) design. The results of the present work revalidate the widely accepted application of IRAAs to monitor yields in SPPS, and confirm the reliability of PAL methodology for the preparation of C‐terminal peptide amides.
AB - Under the normal conditions of acidolytic cleavage/deprotection of tris(a1koxy)benzylamide (PAL) anchoring linkages in Fmoc solid‐phase peptide synthesis (SPPS), product release occurs by a straightforward single‐step pathway. A recently reported cleavage of the NH‐VH bond of an amino acyl residue adjacent to PAL [see Int. J. Peptide Protein Res.38, 146–153 (1991)] could not be confirmed in novel experiments incorporating a double “internal reference” amino acid (IRAA) design. The results of the present work revalidate the widely accepted application of IRAAs to monitor yields in SPPS, and confirm the reliability of PAL methodology for the preparation of C‐terminal peptide amides.
KW - 5‐(4‐(9‐fluorenylmethyloxycarbonyl)aminomethyl‐3,5‐dimethoxyphenoxy)valeric acid
KW - 9‐fluorenylmethyloxycarbonyl
KW - C‐terminal peptide amides
KW - acidolytic cleavage condition
KW - handles
KW - solid‐phase peptide synthesis
KW - “internal reference” amino acids
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U2 - 10.1111/j.1399-3011.1993.tb00339.x
DO - 10.1111/j.1399-3011.1993.tb00339.x
M3 - Article
C2 - 8463054
AN - SCOPUS:0027460245
SN - 0367-8377
VL - 41
SP - 307
EP - 312
JO - International Journal of Peptide and Protein Research
JF - International Journal of Peptide and Protein Research
IS - 3
ER -