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Claudia U. Hjørringgaard Andreas Brust Paul F. Alewood 《Journal of peptide science》2012,18(3):199-207
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. 相似文献
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Christina Ann Chantell Michael Abayomi Onaiyekan Mahendra Menakuru 《Journal of peptide science》2012,18(2):88-91
The ability to speed up conventional Fmoc solid‐phase peptide synthesis (SPPS) has many advantages including increased productivity. One way to speed up conventional Fmoc SPPS is the choice of activator. Recently, several new activators have been introduced into the market, and they were evaluated along with some older activators for their ability to synthesize a range of peptides with shorter and longer reaction times. It was found that HDMC, PyClock, COMU, HCTU, and HATU worked well at shorter reaction times (2 × 1 min), but PyOxim and TFFH only worked well at longer reaction times. The performance of PyBOP at shorter reaction times was poor only for more difficult sequences. These results are important for selecting an appropriate activator for fast SPPS applications. Copyright © 2011 European Peptide Society and John Wiley & Sons, Ltd. 相似文献
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Fast conventional Fmoc solid-phase peptide synthesis with HCTU. 总被引:1,自引:0,他引:1
Christina A Hood German Fuentes Hirendra Patel Karen Page Mahendra Menakuru Jae H Park 《Journal of peptide science》2008,14(1):97-101
1H-Benzotriazolium 1-[bis(dimethyl-amino)methylene]-5-chloro-hexafluorophosphate (1-),3-oxide (HCTU) is a nontoxic, nonirritating and noncorrosive coupling reagent. Seven biologically active peptides (GHRP-6, (65-74)ACP, oxytocin, G-LHRH, C-peptide, hAmylin(1-37), and beta-amyloid(1-42)) were synthesized with reaction times reduced to deprotection times of 3 min or less and coupling times of 5 min or less using HCTU as the coupling reagent. Expensive coupling reagents or special techniques were not used. Total peptide synthesis times were dramatically reduced by as much as 42.5 h (1.8 days) without reducing the crude peptide purities. It was shown that HCTU can be used as an affordable, efficient coupling reagent for fast Fmoc solid-phase peptide synthesis. 相似文献
4.
Giuseppina Sabatino Barbara Mulinacci Maria C. Alcaro Mario Chelli Paolo Rovero Anna M. Papini 《Letters in Peptide Science》2002,9(2-3):119-123
The efficiency of a series of well-known coupling reagents (TBTU, HATU, and PyBOP) and of new in situ activating reagents (TCTU, HCTU, and DMTMM) was compared by synthesizing the 65–74 fragment of the Acyl Carrier Protein (H-Val-Gln-Ala-Ala-Ile-Asp-Tyr-Ile-Asn-Gly-NH2), containing `a difficult sequence', as a test peptide, in a multiple peptide synthesizer. The longer sequence rMOG(35–55) was also synthesized. It was clear that the aminium salts are more efficient than the phosphonium salt (PyBOP) and that the new 6Cl-HOBt based reagents (HCTU and particularly TCTU) are very efficient, while DMTMM appeared to be not suitable for SPPS. 相似文献
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Sabatino Giuseppina Mulinacci Barbara Alcaro Maria C. Chelli Mario Rovero Paolo Papini Anna M. 《International journal of peptide research and therapeutics》2002,9(2-3):119-123
Summary The efficiency of a series of well-known coupling reagents (TBTU, HATU, and PyBOP) and of newin situ activating reagents (TCTU, HCTU, and DMTMM) was compared by synthesizing the 65–74 fragment of the Acyl Carrier Protein (H-Val-Gln-Ala-Ala-Ile-Asp-Tyr-Ile-Asn-Gly-NH2), containing ‘a difficult sequence’, as a test peptide, in a multiple peptide synthesizer. The longer sequence rMOG(35–55)
was also synthesized. It was clear that the aminium salts are more efficient than the phosphonium salt (PyBOP) and that the
new 6Cl-HOBt based reagents (HCTU and particularly TCTU) are very efficient, while DMTMM appeared to be not suitable for SPPS. 相似文献
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