Fmoc-S-4-methyltrityl-L-cysteine
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Fmoc-S-4-methyltrityl-L-cysteine

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Category
Fmoc-Amino Acids
Catalog number
BAT-003828
CAS number
269067-38-1
Molecular Formula
C38H33NO4S
Molecular Weight
599.75
Fmoc-S-4-methyltrityl-L-cysteine
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(4-methylphenyl)-diphenylmethyl]sulfanylpropanoic acid
Synonyms
Fmoc-L-Cys(Mtt)-OH; N-[(9H-Fluoren-9-Ylmethoxy)Carbonyl]-S-[(4-Methylphenyl)(Diphenyl)Methyl]-L-Cysteine; (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(4-methylphenyl)-diphenylmethyl]sulfanylpropanoic acid
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Density
1.256±0.06 g/cm3
Melting Point
107-114 °C
Boiling Point
772.7±60.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C38H33NO4S/c1-26-20-22-29(23-21-26)38(27-12-4-2-5-13-27,28-14-6-3-7-15-28)44-25-35(36(40)41)39-37(42)43-24-34-32-18-10-8-16-30(32)31-17-9-11-19-33(31)34/h2-23,34-35H,24-25H2,1H3,(H,39,42)(H,40,41)/t35-/m0/s1
InChI Key
PCCZXLMDPCBTSL-DHUJRADRSA-N
Canonical SMILES
CC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)SCC(C(=O)O)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46

Fmoc-S-4-methyltrityl-L-cysteine is a derivative of the amino acid cysteine, used in peptide synthesis and biochemical research. Here are some key applications of Fmoc-S-4-methyltrityl-L-cysteine:

Solid-phase Peptide Synthesis: Fmoc-S-4-methyltrityl-L-cysteine is used in solid-phase peptide synthesis (SPPS) as a cysteine building block. The Fmoc group protects the amino group, while the 4-methyltrityl group protects the thiol side chain, facilitating the sequential addition of amino acids. This enables the synthesis of peptides with precise sequences, which are critical for research in biochemistry and drug development.

Protein Engineering: This compound serves as a crucial protective group in protein engineering studies, allowing researchers to introduce cysteine residues into proteins without unwanted side reactions. By selectively deprotecting the 4-methyltrityl group, scientists can introduce specific disulfide bonds or modifications at desired locations. This is essential for designing proteins with novel functionalities or improved stability.

Structural Biology: In structural biology, Fmoc-S-4-methyltrityl-L-cysteine is employed to create cysteine-rich peptides or proteins for NMR or X-ray crystallography studies. These studies require high-purity peptides with specific amino acid sequences to elucidate protein structures and interactions. By using this compound, researchers can obtain the high-quality samples necessary for detailed structural analysis.

Bioconjugation: The compound is also used in bioconjugation techniques to link peptides or proteins to various probes, tags, or other biomolecules. The protected thiol group of Fmoc-S-4-methyltrityl-L-cysteine can be deprotected and then conjugated to maleimide or other thiol-reactive groups. This allows for the creation of multifunctional biomolecules for use in diagnostics, therapeutic delivery, or biochemical assays.

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