Evaluation of COMU as a coupling reagent for in situ neutralization Boc solid phase peptide synthesis
Identifieur interne : 002378 ( Main/Exploration ); précédent : 002377; suivant : 002379Evaluation of COMU as a coupling reagent for in situ neutralization Boc solid phase peptide synthesis
Auteurs : Claudia U. Hj Rringgaard [Australie, Danemark] ; Andreas Brust [Australie] ; Paul F. Alewood [Australie]Source :
- Journal of Peptide Science [ 1075-2617 ] ; 2012-03.
English descriptors
- Teeft :
- Albericio, Alewood, Alewood figure, Amide, Amide bond formation, Amino, Amino acids, Chem, Chemical synthesis, Chemmatrix resin, Chemmatrixw, Chemmatrixw resin, Comparative study, Comu, Copyright, Crude constitution, Crude product, Deletion, Deletion products, Dipea, Ester species, European peptide society, Fmoc, Hbtu, Hctu, Hctu hbtu comu, Hplc, Hplc traces, John wiley sons, Lett, Linker, Neutralization, Neutralization protocol, Ninhydrin, Pept, Peptide, Peptide synthesis, Quantitative ninhydrin test, Reagent, Resin, Scal, Scal linker, Solid phase peptide synthesis, Spps, Tetrahedron, Tetrahedron lett.
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. Copyright © 2012 European Peptide Society and John Wiley & Sons, Ltd.
A coupling efficiency study of COMU versus the benzotriazole‐based HBTU and HCTU, with the use of fast in situ neutralization Boc‐SPPS: Difficult sequences, synthesized on polystyrene‐based and polyethylene glycol‐based resins, were investigated. COMU coupling efficiency was less effective compared to HBTU and HCTU. The improvement of the microenvironment, through the use of a PEG resin with a safety catch amide (SCAL) linker, resulted in the improvement of the coupling efficiency, with HCTU ≥ HBTU > COMU.
Url:
DOI: 10.1002/psc.1438
Affiliations:
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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. Copyright © 2012 European Peptide Society and John Wiley & Sons, Ltd.</div><div type="abstract">A coupling efficiency study of COMU versus the benzotriazole‐based HBTU and HCTU, with the use of fast in situ neutralization Boc‐SPPS: Difficult sequences, synthesized on polystyrene‐based and polyethylene glycol‐based resins, were investigated. COMU coupling efficiency was less effective compared to HBTU and HCTU. The improvement of the microenvironment, through the use of a PEG resin with a safety catch amide (SCAL) linker, resulted in the improvement of the coupling efficiency, with HCTU ≥ HBTU > COMU.</div></front></TEI><affiliations><list><country><li>Australie</li><li>Danemark</li></country></list><tree><country name="Australie"><noRegion><name sortKey="Hj Rringgaard, Claudia U" sort="Hj Rringgaard, Claudia U" uniqKey="Hj Rringgaard C" first="Claudia U." last="Hj Rringgaard">Claudia U. Hj Rringgaard</name></noRegion><name sortKey="Alewood, Paul F" sort="Alewood, Paul F" uniqKey="Alewood P" first="Paul F." last="Alewood">Paul F. Alewood</name><name sortKey="Alewood, Paul F" sort="Alewood, Paul F" uniqKey="Alewood P" first="Paul F." last="Alewood">Paul F. Alewood</name><name sortKey="Alewood, Paul F" sort="Alewood, Paul F" uniqKey="Alewood P" first="Paul F." last="Alewood">Paul F. 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