Fmoc-L-hCys(SIT)-OH

Nombre químico: N-alpha-(9-Fluorenylmethyloxycarbonyl)-S-(sec-isoamyl mercaptan)-L-homocysteine // Sinónimos: N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-((3-methylbutan-2-yl)thio)-L-homocysteine

  • Nº Artículo:FAA8865
  • Fórmula:C24H29NO4S2
  • Storage temperature:-20°C
  • Masa molecular:459,62 g/mol

from 560,00 €

Grouped product items
Cantidad Unidad de venta Precio Unidad de almacenamiento de stock (SKU) Disponibilidad
1 g
560,00 €
FAA8865.0001
<10 días laborables
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

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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