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Journal of Peptide Science

Journal of Peptide Science

IF: 1.8
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Preventing aspartimide formation in Fmoc SPPS of Asp-Gly containing peptides — practical aspects of new trialkylcarbinol based protecting groups

Published:11 January 2016 DOI: 10.1002/psc.2844
Raymond Behrendt, Simon Huber, Peter White

Abstract

In our efforts to develop a universal solution to the problem of aspartimide formation in Fmoc SPPS, we investigated the application of our new β-trialkylmethyl protected aspartic acid building blocks to the synthesis of peptides containing the Asp-Gly motif. The Nα-Fmoc aspartic acid β-tri-(ethyl/propyl/butyl)methyl esters were used in the synthesis of the classic model peptide scorpion toxin II (VKDGYI), and their effectiveness in minimising aspartimide formation during extended piperidine treatments was evaluated. Furthermore, we compared their efficacy against that of the commonly used approach of adding acids to the Fmoc deprotection solution. Finally, we applied our aspartic acid building blocks to the stepwise Fmoc SPPS of teduglutide, a human GLP-2 analogue, whose synthesis is made challenging by extensive aspartimide formation. In all experiments, our approach led to almost complete reduction of aspartimide formation with accompanied suppression of aspartic acid epimerisation. Copyright ? 2016 European Peptide Society and John Wiley & Sons, Ltd.

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Related products
Procduct Name CAS Molecular Formula Supplier Price
L-ASPARTIC ACID 6899-03-2 C4H7NO4 250 suppliers Inquiry
Fmoc-Tyr(Me)-OH 77128-72-4 C25H23NO5 208 suppliers $10.00-$2700.00
Teduglutide 197922-42-2 C164H252N44O55S 184 suppliers Inquiry
GLP-2 (HUMAN) 223460-79-5 C165H254N44O55S 88 suppliers $180.00-$5880.00
FMoc-D-Arg-OH HCl 214852-44-5 C21H25ClN4O4 23 suppliers $107.00-$1430.00
SCORPION VENOM SCORPIO MAURUS PALMATUS 188240-41-7 C145H232N46O46S8 11 suppliers $215.00-$215.00
Fatty acids, vegetable-oil, Me esters 68990-52-3 6 suppliers Inquiry
aspartimide 5615-80-5 C4H6N2O2 2 suppliers Inquiry

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