Acidolytic cleavage of tris(alkoxy)benzylamide (PAL) “internal reference” amino acyl (IRAA) anchoring linkages: validation of accepted procedures in solid‐phase peptide synthesis (SPPS)
- 1 March 1993
- journal article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 41 (3) , 307-312
- https://doi.org/10.1111/j.1399-3011.1993.tb00339.x
Abstract
Under the normal conditions of acidolytic cleavage/deprotection of tris(alkoxy)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--alpha CH 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.Keywords
This publication has 18 references indexed in Scilit:
- Cleavage kinetics and anchor linked intermediates in solid phase peptide amide synthesisInternational Journal of Peptide and Protein Research, 1991
- A cleavage method which minimizes side reactions following Fmoc solid phase peptide synthesisInternational Journal of Peptide and Protein Research, 1990
- Preparation and application of the 5-(4-(9-fluorenylmethyloxycarbonyl)aminomethyl-3,5-dimethoxyphenoxy)-valeric acid (PAL) handle for the solid-phase synthesis of C-terminal peptide amides under mild conditionsThe Journal of Organic Chemistry, 1990
- Synthesis of peptide amides by Fmoc‐solid‐phase peptide synthesis and acid labile anchor groupsInternational Journal of Peptide and Protein Research, 1989
- A modified benzhydrylamine - A useful handle reagent for Fmoc based solid phase synthesis of peptide amidesCollection of Czechoslovak Chemical Communications, 1988
- Solid‐phase peptide synthesis: a silver anniversary report*International Journal of Peptide and Protein Research, 1987
- An acid‐labile anchoring linkage for solid‐phase synthesis of C‐terminal peptide amides under mild conditions*International Journal of Peptide and Protein Research, 1987
- Solid Phase SynthesisScience, 1986
- Improved approach for anchoring Nα‐9‐fluorenylmethyloxycarbonylamino acids as p‐alkoxybenzyl esters in solid‐phase peptide synthesisInternational Journal of Peptide and Protein Research, 1985
- Solid Phase Peptide Synthesis. I. The Synthesis of a TetrapeptideJournal of the American Chemical Society, 1963