Synthesis of peptide amides using Fmoc‐based solid‐phase procedures on 4‐methylbenzhydrylamine resins
- 1 August 1995
- journal article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 46 (2) , 174-180
- https://doi.org/10.1111/j.1399-3011.1995.tb01333.x
Abstract
A two-step low-high protocol for the efficient synthesis of peptide amides is described. The protocol exploits the efficiency of Reagent K for side-chain deprotection with the capability of the hard acid trifluoromethane-sulfonic acid (TFSMA) for cleavage of the peptide from the benzhydrylamine resin. This procedure has proven to be an effective method for the synthesis of peptide amides. The formation of alpha-aminosuccinimide (Asu) derivatives were observed with aspartyl-containing peptides as a minor side reaction product of this procedure, but this Asp-->Asu rearrangement could be successfully suppressed by employing low temperature conditions. The N- to O-acyl rearrangement of threonine and/or serine residues also only occurred to a minor extent under these synthetic conditions.Keywords
This publication has 17 references indexed in Scilit:
- Hypoglycaemic activity of an analogue of human growth hormone [6-13] incorporating a d-ala-pro dipeptide unitBioorganic & Medicinal Chemistry Letters, 1993
- Comparison of methods for the Fmoc solid‐phase synthesis and cleavage of a peptide containing both tryptophan and arginineInternational Journal of Peptide and Protein Research, 1993
- Application of arylsulphonyl side-chain protected arginines in solid-phase peptide synthesis based on 9- fluorenylmethoxycarbonyl amino protecting strategyInternational Journal of Peptide and Protein Research, 1992
- Solid phase peptide synthesis utilizing 9‐fluorenylmethoxycarbonyl amino acidsInternational Journal of Peptide and Protein Research, 1990
- Solid phase synthesis of bioadhesive analogue peptides with trifluoromethanesulfonic acid cleavage from PAM resinInternational Journal of Peptide and Protein Research, 1989
- Methodological implications of simultaneous solid-phase peptide synthesis. 1. Comparison of different coupling proceduresThe Journal of Organic Chemistry, 1988
- Synthetic peptide antagonists of glucagon.Proceedings of the National Academy of Sciences, 1987
- NG-2,2,5,7,8-pentamethylchroman-6-sulphonyl-L-arginine: A new acid labile derivative for peptide synthesisTetrahedron Letters, 1987
- SN 1 and SN 2 mechanisms for the deprotection of synthetic peptides by hydrogen fluorideInternational Journal of Peptide and Protein Research, 1983
- Peptide synthesis. Part 2. Procedures for solid-phase synthesis using Nα-fluorenylmethoxycarbonylamino-acids on polyamide supports. Synthesis of substance P and of acyl carrier protein 65–74 decapeptideJournal of the Chemical Society, Perkin Transactions 1, 1981