Tetrahydropyranyl and Tetrahydrofuranyl as New Backbone Protecting Groups For Enhanced Fmoc SPPS

Acidic Cleavage Deprotection KineticsTHP and THF protected dipeptides with general structure Fmoc-Gly-(PG)Gly-OH, were reacted in cleavage solutions containing various amounts of TFA, monitored over a 3-hour period.They were compared to the Dmb group and a pseudoproline (Ser( Me,Me Pro)) * motif.Results: Tetrahydrofuran (THF) is hyper acid-labile Tetrahydropyran (THP) can be removed in mild cleavage cocktails Order of reactivity; THF > Me,Me Pro > THP > Dmb

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Publication Details

Published
2024-09-20
DOI
https://doi.org/10.17952/37eps.2024.p2034
Primary Topic
Electrospun Nanofibers in Biomedical Applications
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article
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article

Tetrahydropyranyl and Tetrahydrofuranyl as New Backbone Protecting Groups For Enhanced Fmoc SPPS

Craig A. Hutton, Samuel J. Paravizzini, John A. Karas
Electrospun Nanofibers in Biomedical Applications
article

Tetrahydropyranyl and Tetrahydrofuranyl as New Backbone Protecting Groups For Enhanced Fmoc SPPS

Craig A. Hutton, Samuel J. Paravizzini, John A. Karas
article en

Abstract

Acidic Cleavage Deprotection KineticsTHP and THF protected dipeptides with general structure Fmoc-Gly-(PG)Gly-OH, were reacted in cleavage solutions containing various amounts of TFA, monitored over a 3-hour period.They were compared to the Dmb group and a pseudoproline (Ser( Me,Me Pro)) * motif.Results: Tetrahydrofuran (THF) is hyper acid-labile Tetrahydropyran (THP) can be removed in mild cleavage cocktails Order of reactivity; THF > Me,Me Pro > THP > Dmb

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Electrospun Nanofibers in Biomedical Applications
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Tetrahydropyranyl and Tetrahydrofuranyl as New Backbone Protecting Groups For Enhanced Fmoc SPPS — Craig A. Hutton, Samuel J. Paravizzini, et al. · (2024) | TGRS Research Map | TGRS