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Journal of Peptide Science

Journal of Peptide Science

IF: 1.8
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Reduction of cysteine-S-protecting groups by triisopropylsilane

Published:24 October 2018 DOI: 10.1002/psc.3130 PMID: 30353614
Emma J. Ste.Marie, Robert J. Hondal

Abstract

Triisopropylsilane (TIS), a hindered hydrosilane, has long been utilized as a cation scavenger for the removal of amino acid protecting groups during peptide synthesis. However, its ability to actively remove S-protecting groups by serving as a reductant has largely been mischaracterized by the peptide community. Here, we provide strong evidence that TIS can act as a reducing agent to facilitate the removal of acetamidomethyl (Acm), 4-methoxybenzyl (Mob), and tert-butyl (But) protecting groups from cysteine (Cys) residues in the presence of trifluoroacetic acid (TFA) at 37?°C. The lability of the Cys protecting groups in TFA/TIS (98/2) in this study are in the order: Cys(Mob)?>?Cys(Acm)?>?Cys(But), with Cys(Mob) being especially labile. Unexpectedly, we found that TIS promoted disulfide formation in addition to aiding in the removal of the protecting group. Our results raise the possibility of using TIS in orthogonal deprotection strategies of Cys-protecting groups following peptide synthesis as TIS can be viewed as a potential deprotection agent instead of merely a scavenger in deprotection cocktails based on our results. We also tested other common scavengers under these reaction conditions and found that thioanisole and triethylsilane were similarly effective as TIS in enhancing deprotection and catalyzing disulfide formation. Our findings reported herein show that careful consideration should be given to the type of scavenger used when it is desirable to preserve the Cys-protecting group. Additional consideration should be given to the concentration of scavenger, temperature of the reaction, and reaction time.

Substances (10)

Related products
Procduct Name CAS Molecular Formula Supplier Price
L-Cysteine 52-90-4 C3H7NO2S 1289 suppliers $3.00-$16760.00
Trifluoroacetic acid 76-05-1 C2HF3O2 827 suppliers $9.00-$12230.00
Triethylsilane 617-86-7 C6H16Si 641 suppliers $6.00-$4500.00
Triisopropylsilane 6485-79-6 C9H22Si 452 suppliers $5.00-$1423.00
Thioanisole 100-68-5 C7H8S 431 suppliers $5.00-$6815.66
Sodium 5-[(4-Amino-1-naphthyl)azo]-2-[4-[(2-hydroxy-1-naphthyl)azo]-2-sulfonatostyryl]benzenesulfonate 6459-79-6 C34H26N5NaO7S2 121 suppliers $10.16-$77.00
tert-Butyl peroxyacetate 107-71-1 C6H12O3 85 suppliers $68.20-$3212.06
ANISYL PHENYLACETATE 102-17-0 C16H16O3 45 suppliers $36.65-$12679.40
S,S,S,S,S-Trandolapril Hydrochloride 6 suppliers Inquiry
2,4-dichloro-5-(acetamidomethyl)benzene-1-sulfonyl chloride 1 suppliers Inquiry

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