Fmoc-S-4-methoxybenzyl-L-cysteine
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Fmoc-S-4-methoxybenzyl-L-cysteine

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Category
Fmoc-Amino Acids
Catalog number
BAT-003824
CAS number
141892-41-3
Molecular Formula
C26H25NO5S
Molecular Weight
463.60
Fmoc-S-4-methoxybenzyl-L-cysteine
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(4-methoxyphenyl)methylsulfanyl]propanoic acid
Synonyms
Fmoc-L-Cys(pMeOBzl)-OH; Fmoc-Cys(PMeOBzl)-OH; Fmoc-S-p-methoxybenzyl-L-cysteine; FMOC-CYS(4-MEOBZL)-OH; N-Fmoc-S-(4-methoxybenzyl)-L-cysteine; Fmoc-S-4-methoxybenzyl-L-cysteine
Appearance
White powder
Purity
≥ 99% (HPLC)
Density
1.295±0.06 g/cm3
Melting Point
138-144 °C
Boiling Point
689.5±55.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C26H25NO5S/c1-31-18-12-10-17(11-13-18)15-33-16-24(25(28)29)27-26(30)32-14-23-21-8-4-2-6-19(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
IWZGYHFOLFRYPK-DEOSSOPVSA-N
Canonical SMILES
COC1=CC=C(C=C1)CSCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-S-4-methoxybenzyl-L-cysteine, a protected amino acid central to peptide synthesis, finds diverse applications in various fields. Here are four key applications:

Solid-Phase Peptide Synthesis: Embedded within the solid-phase peptide synthesis (SPPS) methodology, Fmoc-S-4-methoxybenzyl-L-cysteine plays a pivotal role in crafting intricate peptides. By safeguarding the thiol group of cysteine through chain assembly, it ensures the precise formation of desired peptide bonds. This meticulous process enables the efficient and accurate construction of diverse peptide sequences, crucial for advancing biochemical research.

Protein Engineering: At the forefront of protein engineering, Fmoc-S-4-methoxybenzyl-L-cysteine facilitates the synthesis of tailored proteins with distinct functional attributes. By incorporating this guarded amino acid, researchers can strategically introduce cysteine residues at specific sites within a protein. This customization is fundamental for investigating protein interactions, folding dynamics, and structural stability in depth.

Pharmaceutical Development: Serving as a cornerstone in the creation of therapeutic peptides and proteins, Fmoc-S-4-methoxybenzyl-L-cysteine is indispensable in pharmaceutical development. Its protective group empowers the synthesis of peptides that exhibit both stability and bioactivity, essential qualities for effective drug design. This capability streamlines the production of peptide-based therapeutics, known for their exceptional specificity and clinical efficacy.

Chemical Biology: Within the realm of chemical biology, Fmoc-S-4-methoxybenzyl-L-cysteine emerges as a vital tool for synthesizing peptide probes and inhibitors. These molecular constructs play a critical role in unraveling intricate biological pathways and deciphering enzyme functionalities. The precision inherent in this amino acid’s involvement in peptide synthesis elevates its significance as a potent instrument for deciphering the complexities of biological systems.

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