Fmoc-S-benzyl-L-cysteine
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Fmoc-S-benzyl-L-cysteine

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Category
Fmoc-Amino Acids
Catalog number
BAT-003831
CAS number
53298-33-2
Molecular Formula
C25H23NO4S
Molecular Weight
433.53
Fmoc-S-benzyl-L-cysteine
IUPAC Name
(2R)-3-benzylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
Fmoc-L-Cys(Bzl)-OH; Fmoc-(S)-2-amino-3-(S-benzylthio)propanoic acid; (2R)-3-benzylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid; Fmoc-Cys(Bzl)-OH
Appearance
Solid
Purity
≥ 99% (HPLC)
Density
1.298±0.06 g/cm3
Melting Point
124-130 °C
Boiling Point
663.2±55.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C25H23NO4S/c27-24(28)23(16-31-15-17-8-2-1-3-9-17)26-25(29)30-14-22-20-12-6-4-10-18(20)19-11-5-7-13-21(19)22/h1-13,22-23H,14-16H2,(H,26,29)(H,27,28)/t23-/m0/s1
InChI Key
AKXYVGAAQGLAMD-QHCPKHFHSA-N
Canonical SMILES
C1=CC=C(C=C1)CSCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-S-benzyl-L-cysteine, a prominent chemical reagent in peptide synthesis, finds diverse applications in various fields. Here are four key applications of Fmoc-S-benzyl-L-cysteine:

Peptide Synthesis: Central to drug development and biochemical research, Fmoc-S-benzyl-L-cysteine plays a pivotal role in solid-phase peptide synthesis. The Fmoc group acts as a transient protective shield for the amino function, facilitating the systematic construction of peptides. This meticulous approach ensures optimal purity and efficiency in generating bespoke peptides tailored for specific applications.

Protein Engineering: Within the realm of protein engineering, Fmoc-S-benzyl-L-cysteine is harnessed to introduce precise cysteine residues into proteins. These cysteine residues are instrumental in forming disulfide bonds, crucial for the structural integrity and functionality of proteins. This technique is indispensable for crafting engineered proteins endowed with enhanced or novel properties, pushing the boundaries of protein design.

Bioconjugation: Acting as a versatile linker in bioconjugation methodologies, Fmoc-S-benzyl-L-cysteine facilitates the attachment of biomolecules like proteins or peptides onto diverse substrates. This capability is particularly valuable in the development of cutting-edge biosensors, targeted drug delivery systems, and diagnostic assays. The benzyl protecting group ensures specific and controlled attachment, elevating the performance of the resultant conjugates in various applications.

Chemical Biology: In the dynamic field of chemical biology, Fmoc-S-benzyl-L-cysteine stands as a foundational building block for synthesizing modified peptides and small molecules employed in dissecting biological systems. By incorporating these modified peptides, researchers can probe protein interactions, enzyme mechanisms, and cellular processes, gaining deeper insights into biological mechanisms and identifying potential therapeutic targets. This application empowers researchers to unravel the intricacies of biological processes with precision and depth.

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