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Fmoc-L-Cys(SIT)-OH
Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-S-(sec-isoamyl mercaptan)-L-cysteine // Synonyms: 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
- Product code:FAA8495
- CAS No.:2545642-31-5
- Formula:C23H27NO4S2
- Storage temperature:2-8°C
- Molecular weight: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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