Fmoc-S-4-methylbenzyl-L-cysteine
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Fmoc-S-4-methylbenzyl-L-cysteine

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Category
Fmoc-Amino Acids
Catalog number
BAT-003827
CAS number
136050-67-4
Molecular Formula
C26H25NO4S
Molecular Weight
447.60
Fmoc-S-4-methylbenzyl-L-cysteine
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(4-methylphenyl)methylsulfanyl]propanoic acid
Synonyms
Fmoc-L-Cys(pMeBzl)-OH; Fmoc-Cys(pMeBzl)-OH; FMOC-CYS(4-MBZL)-OH; Fmoc-Cys(Mbzl)-OH; Fmoc-Cys(4-MeBzl)-OH; Fmoc-S-(4-methylbenzyl)-L-cysteine
Appearance
White powder
Purity
≥ 98%
Density
1.278±0.06 g/cm3
Melting Point
151-157 °C
Boiling Point
671.7±55.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C26H25NO4S/c1-17-10-12-18(13-11-17)15-32-16-24(25(28)29)27-26(30)31-14-23-21-8-4-2-6-19(21)20-7-3-5-9-22(20)23/h2-13,23-24H,14-16H2,1H3,(H,27,30)(H,28,29)/t24-/m0/s1
InChI Key
OQYBTXFHTQYWCZ-DEOSSOPVSA-N
Canonical SMILES
CC1=CC=C(C=C1)CSCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-S-4-methylbenzyl-L-cysteine, a protected amino acid, finds diverse applications in peptide synthesis and biochemical studies. Here are four key applications:

Peptide Synthesis: As a crucial component in solid-phase peptide synthesis (SPPS), Fmoc-S-4-methylbenzyl-L-cysteine plays a pivotal role in the meticulous construction of peptides. The Fmoc (9-fluorenylmethyloxycarbonyl) group acts as a protective cloak during synthesis, ensuring precise reactions at the cysteine residue. This meticulous process results in the production of high-purity peptides, critical for both research and therapeutic endeavors.

Protein Labeling: In the realm of protein labeling studies, Fmoc-S-4-methylbenzyl-L-cysteine emerges as a key player in the development of peptide-based probes. By incorporating this amino acid into peptides, researchers introduce reactive sulfhydryl groups that serve as sites for fluorescent or affinity tags. This application is indispensable for exploring protein interactions, dynamics, and localization within complex biological systems.

Drug Development: In the arena of drug development, Fmoc-S-4-methylbenzyl-L-cysteine assumes a crucial role in the design and synthesis of peptide-based drugs or peptidomimetics. Its incorporation allows for the introduction of modified cysteine residues, enhancing drug stability, specificity, and bioavailability. This innovative approach is instrumental in crafting novel therapeutics targeting specific disease pathways.

Bioconjugation: Through bioconjugation techniques, Fmoc-S-4-methylbenzyl-L-cysteine facilitates the linking of peptides or proteins to other biomolecules or surfaces. The unique reactivity of its cysteine moiety enables the formation of stable thioether or disulfide bonds, creating complex biomaterials crucial for biomedical applications. These applications extend to the development of targeted drug delivery systems and cutting-edge biosensors, advancing the frontiers of biomedical research and innovation.

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