Evaluation of COMU as a coupling reagent for in situ neutralization Boc solid phase peptide synthesis

Hjorringgaard, Claudia U., Brust, Andreas and Alewood, Paul F. (2012) Evaluation of COMU as a coupling reagent for in situ neutralization Boc solid phase peptide synthesis. Journal of Peptide Science, 18 3: 199-207. doi:10.1002/psc.1438


Author Hjorringgaard, Claudia U.
Brust, Andreas
Alewood, Paul F.
Title Evaluation of COMU as a coupling reagent for in situ neutralization Boc solid phase peptide synthesis
Formatted title
Evaluation of COMU as a coupling reagent for in situ neutralization Boc solid phase peptide synthesis
Journal name Journal of Peptide Science   Check publisher's open access policy
ISSN 1075-2617
1099-1387
Publication date 2012-03
Sub-type Article (original research)
DOI 10.1002/psc.1438
Volume 18
Issue 3
Start page 199
End page 207
Total pages 9
Place of publication Bognor Regis, West Sussex, United Kingdom
Publisher John Wiley & Sons
Collection year 2013
Language eng
Formatted abstract
Benzotriazole-based coupling reagents have dominated the last two decades of solid phase peptide synthesis. However, a growing interest in synthesizing complex peptides has stimulated the search for more efficient and low-cost coupling reagents, such as COMU which has been introduced as a nonexplosive alternative to the classic benzotriazole coupling reagents. Here, we present a comparative study of the coupling efficiency of COMU with the benzotriazole-based HBTU and HCTU for use in in situ neutralization Boc-SPPS. Difficult sequences, such as ACP(65–74), Jung–Redeman 10-mer, and HIV-1 PR(81–99), were used as model target peptides on polystyrene-based resins, as well as polyethylene glycol-based resins. Coupling yields obtained using fast in situ Boc-SPPS cycles were determined with the quantitative ninhydrin test as well as via LC-MS analysis of the crude cleavage products. Our results demonstrate that COMU coupling efficiency was less effective compared to HBTU and HCTU with HCTU ≥ HBTU > COMU, when polystyrene-based resins were employed. However, when the PEG resin was employed in combination with a safety catch amide (SCAL) linker, more comparable yields were observed for the three coupling reagents with the same ranking HCTU ≥ HBTU > COMU.
Keyword Coupling reagents
In situ neutralization Boc-SPPS
COMU
HBTU
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2013 Collection
Institute for Molecular Bioscience - Publications
 
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