Fmoc-S-2-hydroxyethyl-L-cysteine
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Fmoc-S-2-hydroxyethyl-L-cysteine

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Category
Fmoc-Amino Acids
Catalog number
BAT-003848
CAS number
200354-35-4
Molecular Formula
C20H21NO5S
Molecular Weight
387.46
Fmoc-S-2-hydroxyethyl-L-cysteine
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(2-hydroxyethylsulfanyl)propanoic acid
Synonyms
Fmoc-L-Cys(2-hydroxyethyl)-OH; Fmoc-(S)-2-amino-3-(ethanolthio)propanoic acid; (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(2-hydroxyethylsulfanyl)propanoic acid
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.348±0.06 g/cm3
Boiling Point
663.0±55.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C20H21NO5S/c22-9-10-27-12-18(19(23)24)21-20(25)26-11-17-15-7-3-1-5-13(15)14-6-2-4-8-16(14)17/h1-8,17-18,22H,9-12H2,(H,21,25)(H,23,24)/t18-/m0/s1
InChI Key
VDIVFUTVJUGBOW-SFHVURJKSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CSCCO)C(=O)O

Fmoc-S-2-hydroxyethyl-L-cysteine, a derivative employed in peptide synthesis, boasts diverse and impactful applications in bioscience.

Peptide Synthesis: Serving as a foundational component in peptide synthesis, Fmoc-S-2-hydroxyethyl-L-cysteine enables the incorporation of hydroxyl groups into peptides, thereby altering their chemical characteristics and enhancing their biological activities. This modification plays a pivotal role in crafting peptides with tailored functionalities for both research and therapeutic purposes, offering a wide array of possibilities for customization and specialization.

Protein Engineering: Through the integration of Fmoc-S-2-hydroxyethyl-L-cysteine into proteins, researchers can explore the impact of hydroxylation on protein structure and function. This amino acid derivative facilitates the development of proteins with enhanced stability, binding affinities, or enzymatic capabilities, laying the groundwork for the creation of engineered proteins with precise and desired properties. Such advanced protein design opens doors to diverse applications, including the realm of drug development and beyond.

Chemical Biology: Within the realm of chemical biology, Fmoc-S-2-hydroxyethyl-L-cysteine finds its niche in the creation of bioconjugates and probes. The reactive hydroxyl group serves as a focal point for additional chemical alterations, enabling the attachment of diverse biomolecules such as fluorophores or affinity tags. This capability drives exploration into protein interactions, localization, and functionality within intricate biological systems, fostering a deeper understanding of molecular mechanisms and cellular processes.

Materials Science: In the realm of materials science, Fmoc-S-2-hydroxyethyl-L-cysteine emerges as a key player in synthesizing peptidomimetic materials. These materials harness the distinctive properties endowed by the hydroxyl group, including heightened hydrophilicity and potential for further chemical modifications. They find applications in the development of biomaterials for various purposes, ranging from medical devices to tissue engineering and drug delivery systems, showcasing the versatility and adaptability of this innovative compound in shaping the landscape of materials science.

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