Fmoc-(S)-4-methoxybenzyl selenocysteine
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Fmoc-(S)-4-methoxybenzyl selenocysteine

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Category
Fmoc-Amino Acids
Catalog number
BAT-001988
CAS number
150308-80-8
Molecular Formula
C26H25NO5Se
Molecular Weight
510.40
Fmoc-(S)-4-methoxybenzyl selenocysteine
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(4-methoxyphenyl)methylselanyl]propanoic acid
Synonyms
Fmoc-L-Sec(pMeOBzl)-OH
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Boiling Point
708.5±60.0 °C(Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C26H25NO5Se/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
XCPAYIZRJRMXBI-DEOSSOPVSA-N
Canonical SMILES
COC1=CC=C(C=C1)C[Se]CC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-(S)-4-methoxybenzyl selenocysteine, a specialized amino acid derivative, plays a crucial role in peptide synthesis and bioconjugation. Here are four key applications of Fmoc-(S)-4-methoxybenzyl selenocysteine:

Peptide Synthesis: In the realm of solid-phase peptide synthesis (SPPS), Fmoc-(S)-4-methoxybenzyl selenocysteine emerges as a key player, facilitating the incorporation of selenocysteine residues into peptides. This innovative approach results in the generation of selenium-containing peptides, which exhibit distinct chemical properties when compared to their sulfur-containing counterparts. Leveraging the reactivity and redox characteristics of selenium, these peptides become invaluable tools for investigating protein function and advancing the development of therapeutic agents.

Protein Engineering: At the frontier of protein engineering, Fmoc-(S)-4-methoxybenzyl selenocysteine takes center stage as it is harnessed to replace cysteine residues in proteins. This strategic substitution empowers researchers to explore the structural and functional variances between sulfur-containing and selenium-containing proteins. Such in-depth investigations offer profound insights into protein stability, catalysis, and redox mechanisms, pushing the boundaries of our understanding of protein behavior.

Bioconjugation: Offering a gateway to precise bioconjugation reactions, Fmoc-(S)-4-methoxybenzyl selenocysteine showcases its unique reactivity through the selenocysteine side chain. This distinctive feature enables the targeted attachment of diverse molecules, ranging from drugs and probes to polymers, onto peptides and proteins. These tailored conjugates play a pivotal role in the development of targeted therapeutics and diagnostic tools.

Redox Biology Research: In the domain of redox biology research, the distinctive redox properties of selenium come to the fore, offering a valuable lens through which to study oxidative stress and redox signaling pathways. By integrating Fmoc-(S)-4-methoxybenzyl selenocysteine into peptides and proteins, researchers embark on a journey to unravel the intricate roles of selenium in redox regulation.

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