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Fmoc-L-Cys(SIT)-OH
Nom chimique: N-alpha-(9-Fluorenylmethyloxycarbonyl)-S-(sec-isoamyl mercaptan)-L-cysteine // Synonymes: Fmoc-Cys(SIT)-OH, N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-((3-methylbutan-2-yl)thio)-L-cysteine, N-alpha-(9-Fluorenylmethyloxycarbonyl)-S-((3-methylbutan-2-yl)thio)-L-cysteine
- n° Art.:FAA8495
- n° CAS:2545642-31-5
- Formule:C23H27NO4S2
- Storage temperature:2-8°C
- Masse moléculaire:445,59 g/mol
from 200,00 €
description
The disulfide-based Cysteine thiol protecting group sec-isoamyl mercaptan (SIT) is fully compatible with Fmoc/tBu SPPS. In comparison to StBu, it is sterically less hindered and can therefore be easily removed upon treatment with dithiothreitol.
In a comparative study, the deprotection rate of Fmoc-Cys(StBu)-OH and Fmoc-Cys(SIT)-OH by using DTT as reducing agent was monitored by HPLC for 500 min. After that time, StBu was only partially (60%) removed. SIT was totally removed after 160 min. The addition of water (5%) even speeds the reaction: StBu was completely removed in 250 min; SIT in <40 min. Furthermore, this compound expands the toolbox of orthogonal protecting groups required for synthesis of peptides containing multiple disulfide bridges.
references
Disulfide-Based Protecting Groups for the Cysteine Side Chain; A. Chakraborty; A. Sharma; F. Albericio, B. G. de la Torre; Org. Lett. 2020; 22: 9644-9647. https://doi.org/10.1021/acs.orglett.0c03705.
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All information contained in our webshop is compiled to the best of our knowledge.
Prices and product availability are subject to change and require reconfirmation. Please contact us for further information.
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