Fmoc-S-sulfo-L-cysteine disodium
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Fmoc-S-sulfo-L-cysteine disodium

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A useful cysteine derivative for solid-phase synthesis by the Fmoc-strategy.

Category
Fmoc-Amino Acids
Catalog number
BAT-003834
CAS number
163558-30-3
Molecular Formula
C18H15NNa2O7S2
Molecular Weight
467.43
Fmoc-S-sulfo-L-cysteine disodium
Synonyms
Fmoc-L-Cys(SO3H)-OH disodium salt; FMOC-S-SULFO-L-CYSTEINE DISODIUM; Fmoc-S-sulfo-L-cysteine disodium salt
Appearance
White powder
Purity
≥ 99.8% (HPLC, Chiral purity)
Storage
Store at RT
InChI
InChI=1S/C18H17NO7S2.2Na/c20-17(21)16(10-27-28(23,24)25)19-18(22)26-9-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15;;/h1-8,15-16H,9-10H2,(H,19,22)(H,20,21)(H,23,24,25);;/t16-;;/m0../s1
InChI Key
YYUULCRJTNZKJD-SQKCAUCHSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CSS(=O)(=O)O)C(=O)O.[Na].[Na]

Fmoc-S-sulfo-L-cysteine disodium is a specialized amino acid derivative used in peptide synthesis and other applications in bioscience. Here are some key applications of Fmoc-S-sulfo-L-cysteine disodium:

Peptide Synthesis: Fmoc-S-sulfo-L-cysteine disodium is employed in solid-phase peptide synthesis to incorporate cysteine residues with a sulfonate group into peptides. This modification can enhance the water solubility and stability of synthetic peptides. Researchers use it to create peptides with specific structural and functional properties for various biochemical applications.

Protein Engineering: In protein engineering, Fmoc-S-sulfo-L-cysteine disodium is used to introduce chemically reactive sulfonate groups into proteins. This enables site-specific labeling and conjugation of proteins with other molecules, such as fluorescent probes or drugs. This technique is pivotal for studying protein interactions, folding, and function.

Bioconjugation: Fmoc-S-sulfo-L-cysteine disodium serves as a building block for bioconjugation, allowing the attachment of biomolecules to surfaces or other macromolecules. This application is especially useful in the development of biosensors, drug delivery systems, and other bioanalytical tools. By leveraging its unique chemical properties, scientists can create targeted and responsive bioconjugates.

Phosphorylation Studies: Researchers use Fmoc-S-sulfo-L-cysteine disodium in the study of phosphorylation and related post-translational modifications. The sulfonate group mimics the phospho-group, making it a useful analog in the investigation of protein kinases and phosphatases. This aids in elucidating the mechanisms of cell signaling and regulatory pathways.

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